Sex and the Twenties

 My Dearest Readers,

When I started this blog, I honestly didn’t have the faintest idea what I was doing. I simply thought, hey, I love writing and I have a LOT of thoughts on dating… why not combine the two? I had no plan. No goals. I was just having fun.

And now, more than two years later, I am shocked and grateful for how far this blog has come. If you had told me back then, that I would end up having hundreds of thousands of readers who would chime in and offer me (and each other) advice and love and compassion – I would have told you, you were high. But somehow, I was blessed and that is exactly what happened.

This blog has changed my life (yes I know that sounds corny but it’s true) and it’s because of all of you. You all have changed me with your advice, your empathy, your camaraderie, your tough love and even your anger. And through all of this, you have given me an entirely different perspective on dating. I have fundamentally changed how I interpret the things guys do and I think you’ve left me more open minded and forgiving than when I started. For this and for so much more, I am eternally grateful.

But alas, all good things must at some point come to an end, and the time has come for me to put the laptop down. I am (officially!!!) moving to NYC next month, and for me this move is all about having  a clean slate. It’s a chance to close the book on the past and to move forward with all of the wonderful lessons and new perspectives I have gained. And in order to truly do this, I can’t very well be blogging on the same blog with all my past love and heartbreak only a short scroll away.

So what does this mean? Well, I want the site to live on. I take great pride in what we’ve all accomplished here and I love (and welcome) those who are still discovering S&20s. And while I won’t be blogging anymore, that doesn’t mean the site has to be empty. What I’d love to do is find a new Cali Bradshaw. Ideally a single 20 something who likes to date and who loves to write. I’m looking for someone who is funny and sarcastic but also willing to be vulnerable. And most importantly, I’d like to pass the reigns to someone who knows they can handle the punches that come with talking about dating on the internet.

If you think this person could be you, or you know someone perfect for the role, shoot me a note at sexandthetwenties@yahoo.com. While it can be a bit of work, I can tell you first hand, there is nothing in my life that I more proud of. And plus, you’ll be inheriting the best readers a blogger could ask for! This group of men and women are smart, funny and kind. I know that if you are awesome (which you will be, because I picked you :)) that they will welcome you with open arms.

As for me, it’s possible that I’ll get the itch to blog again (although likely on a different subject) and if so, you’ll be the first to know where I’m at. But for now, before I go, I’d like to say one final thank you and goodbye to the true stars of this site – the men I’ve dated. Cheers to you, my dear men. I couldn’t have done this without you! Here are my final words…

Mr. Not Quite Right - I will probably always wonder what would have happened if we had met later in life. There is no denying, we had awesome chemistry and perhaps if we’d been older and more mature, we would have been more equipped to handle it. And then again, maybe not.

Either way, I am sorry for how I acted during and/after our break up and if I could go back in time and change things I would. You are a good man – strong, sensitive, fun –  and I will always be grateful for those few months we spent together. They were truly some of the happiest of my entire life.

Mr. Cute but Whiny - Oh Jake, you are a tough one. On one hand, out of ALL of the guys I’ve dated, I think you are the closest to being like the person I want to end up with. You are smart, and funny and successful and of course, handsome. But you also behave like a real jackass sometimes and I can’t for the life of me figure out why. I am hoping that after our last blow up, you’ve gotten your shit together and realized that that isn’t the kind of boyfriend or friend that you want to be. If not, look alive. You’re better than that. Oh, and I still think Brandi sucks.

D – Saying goodbye to you is both the simplest and hardest thing I’ve ever had to do. On one hand, it’s so easy because you and I make no sense and have a long history of hurting one another. You don’t want what I want in life, you don’t like to do what I like to do, and I am fairly sure that if we ever really got serious, we’d drive each other absolutely nuts. On the other hand, I loved you for a very long time and I think you will always have a tiny piece of my heart. You are the only guy who I have felt totally comfortable being myself around and there is an amazing freedom in knowing that you’ll still be there even when I act like an overly sensitive, dramatic nut or say things I shouldn’t  It’s hard to think about a time where I won’t be going over to your house and staying up all night, laughing for hours about absolutely nothing. And I’d be lying if I said I didn’t already miss the way you hold me and the butterflies I get every time you kiss me (even after 10 freaking years).

But all that being said, I am sure in my decision. You have finally convinced me, you aren’t going to change no matter how much I believe in you. And even though I still think you are selling yourself short, I have given up. I have accepted that you either really will die alone, or more likely, once I am gone you’ll get back together with Cami, and you’ll marry her unimpressive ass because she’ll never challenge you a day in your life. And you know what, I am ok with that. She will take care of you and hopefully make you happy and while you are doing that, I will finally have the freedom to get the future I want.

Dyl, I am absolutely certain, that someday I’ll look back on this and it will all make sense. I’ll know that the many, MANY, lessons I learned with you were what prepared me to be ready for the guy I am meant to be with, and for that I will always be grateful.

And to the rest – Brad (s), The Texter, the lifeguard, the tall guy, my bestie and every guy in between – thank you for the role each and every one of you played. Looking back, it is SO obvious why none of you were right for me, and I take solace in knowing that no matter how intense my feelings were for each of you at one point, that now you are nothing more than a blip on the radar.

With that, there is nothing left to say but farewell! Goodbye my dear readers, I truly love you and will miss you lots. Please, pretty please, keep in touch.

Love always,

CaliB

Anyone who knows me in the slightest knows exactly how much I despise New Years Eve. I loathe it with every ounce of my being. To me, it is worse than inappropriate text messaging, an emo Facebook status, and guys who cancel at the last minute – combined.

And this hatred does not come without good reason. The vast majority of my NYE nights have been super shitty. Like 2003, when my highschool crush told me didn’t like me because I didn’t drink. Or NYE 2005, when my friends all got a limo and wanted to spend the whole night driving around making out with their boyfriends (also same year I got to watch D kiss some random). Or 2006, the year D and I managed to get along until 2:00 AM…  at which time we exploded into a major fight that ended in him leaving me at one of his friend’s house – again. Or how about 2008 when we spent 100 bucks to escape everyone and go to a fancy party in another town, only to realize it was filled with the same fucking people we saw at the bars every other night. Good times, right?

But this year, this year, was going to be different! I was determined to have a little fun – nothing crazy, just a few friends at the local bars, maybe a hot surfer boy… I dunno – just something with an air of festivity. It seemed appropriate seeing as how I’ve decided 2013 is going to be awesome. Why shouldn’t said awesomeness to start from the very first moment?

Of course, as quickly as that thought passed my mind, things started to go wrong. We got out later than I had hoped (leaving me oh-so-sober at the bars), our friends couldn’t make it so it ended up being just me and one of my besties (whom I adore, but still, I was hardly feeling popular), and then there was not even one single surfer boy at the bar to swoon over. Not looking promising…

Thinking quickly we decided to check out bar number 2. I mean hey, it was only like 10:45, there was still time! I could still start the YEAR I MOVE TO NEW YORK (official name) out on the right foot. With any luck we’d run into a bunch of people we knew (and liked) and we’d hang out and dance the night away!

But alas, bar number 2 was a bust. We met a nice girl who we chatted with for a bit  - until she made us feel old as balls when she told us how she’d just been traveling since graduation. Aw, youth. And rather then dwell on how we became so old and so single, we felt it best to move on.

So at 11PM, I begrudgingly agreed to go to my least favorite bar, figuring, the night could only go up from there. Naturally, there was a line (how this shitty bar is popular is beyond me) but there was nowhere else to go, so there we stood and froze our butts off in our cute little dresses. Minute after minute went by and I was growing more forlorn with every second…  Was this was how I was going to start the year I moved to NY? Stuck in line and freezing. (Probably appropriate, actually…)

And then, something fun happened.

I saw a group of guys I used to know walking up to the bar, including (yaaaay!) one I had a fling with for a few years back in college. Please let me stop you right now if you are going to try and pretend like you wouldn’t be stoked to see someone you could potentially make out with on NYE at midnight. Don’t lie. No one likes awkwardly high five-ing their friends as the ball drops – believe me, I know. I’ve done it many times. So you can stop judging me now for being excited.

In any case, this particular fellow was someone I used to have quite a bit of fun with and although neither of us ever took it seriously, we always stayed in touch via the FB. In fact, over the years I grew to think of him as a friend. A hot friend that I could sleep with without adding a new number. :)

Eventually, while I was away at college, he ended up getting his shit together. Moved to the East Coast, had a real job, even got himself a serious girlfriend for awhile and, well, grew up! And the one time we ran into each other since then I remember thinking I was so freaking happy for him. But other than that one night (and subsequent morning) I hadn’t thought much about him. So imagine my surprise and delight to see him walking towards me at 11:15 PM on NYE.

After many a hugs with the group and exchanging of small talk, I naturally found myself chatting up my past fling. It was a pleasure to talk to him and share everything that had changed for us both over the years, and as we moved up the line, I found myself beginning to look forward to the rest of the night. But then, just as we got to the front of the line, the bar informed us they were done for the night. At 11:30. On NYE. Have I mentioned  I hate this bar??

Realizing there was no where we could get into at this point, the guys invited us to go back to my friend’s house for a drink. Seemed like a logical solution, so off we went and I must say, I ended up having a blast. I hadn’t partied with these guys since college, and I have seriously changed my partying ways since then. But with a bottle of Smirnoff in front of me and the memories flowing, I was all or a sudden right back to college Cali – drunk and slightly giddy. We laughed, chatted, took pictures and I got my New Years kiss (slightly awkward since we were all just standing around the TV and no one else was kissing, but oh well…) And all in all, I felt great about ringing in the New Year surrounded by good peeps.

At the end of the night, and after maybe 5 too many shots, it seemed only natural that my friend and I would fall back into old habits and I honestly, didn’t think twice about crawling into bed with him.

When I woke up the next morning I couldn’t tell how I felt. (Well other than hung over, I definitely felt hung over). On one hand, I had a great time. I still think he’s hot, he’s still my friend, I’m not dating anyone, and it certainly wasn’t like I hadn’t done it before… But on the other hand, I felt sorta weird about it. In the past 2 years, the only guys I have slept with are Mr. Cute but Whiny, My Bestie and really, mostly just D – all situations that are very different than just a friendly fling. And furthermore (as much as you all hate this) the situation with D and how close we have become, really threw a harsh light on my NYE hookup. Turns out, those “just for fun hookups” were a lot more fun when I didn’t know what it was like to have sex with a guy I trusted and loved.

But it wasn’t until I explained it to one of my best girl friends that I actually got any clarity on how I felt. Here’s what I discovered:

Am I sorry it happened? No. It was fun and nostalgic and it put me in a great mood to start out a great year. And because of this, I’ve decided to call it a “Throwback Bang.” Just like the “Throwback Thursdays (#TBT)” pictures we all share on lnstagram, the Throwback Bang (or TBB) leaves you with a smile and a reminder of a happy memory or a simpler time.

That being said, will I be “Throwback Banging” again anytime soon? Probably not. I may be condemning myself to a very long dry spell here, but I think the Throwback Bang may have lost its allure for me. If I am honest with myself, I would have had just as much fun kissing him and calling it a night (And not because the sex wasn’t good, it was!). But that’s just not my style anymore and I am a little sad that I let a old habit and a holiday get the best of me.

What I realized is, sometimes it’s hard to know exactly how we’ve changed until we’ve had ourselves tested, and prior to NYE  I hadn’t had an opportunity figure out my stance on the TBB. So, now I know. And I can move forward into 2013 certain about at least one more thing.

Now I’m curious, what’s your stance on the Throwback Bang? If it won’t cost you a number, it’s still fun and both parties are single – is it fair play? Or do you stay away?

You know what is one thing you are absolutely not supposed to talk about as a single girl? Babies. In fact, not only are you not supposed to talk about them, you probably shouldn’t think about them or heck, even look at one, because if you do, you are the crazy single girl whose biological clock is ticking.

Well, I’ve decided that’s silly. I think the time has come to stop pretending that having a baby isn’t something we’ve all been thinking about for years, no matter where we are in the process of preparing for parenthood.

For me, as a single 27 year old, it is suffice to say that I have conflicted emotions when it comes to child-bearing.  On one hand, the mere thought of caring, supporting and paying for a defenseless human being is enough to make me want to chug a handle of jack, turn up the Kesha and dance naked on a table. On the other hand, I watch the way my friend absolutely lights up around her beautiful newborn and can’t help but think, I want one!! I would love to love anything in this world 1/8 as much as she loves that child.

But the reality is, there is no way I am ready to be a parent tomorrow. (Um hi, I am about to move to NYC for fun and adventure). And yet, even though I know I am not ready now, I am petrified of being 33, single, and having to deal with my biological clock tick-tocking all the live long day. That does not sound pleasant.

So, what to do? Is there any way to prevent such a dire situation in my future?

Well, bad news, I have yet to come up with a foolproof way to avoid this. (Helpful, right?) But I have compiled a few tips I use to deal with the whole baby situation and I thought I’d share in case you too are feeling conflicted on the topic.

The first realization I’ve had is that we have to stop judging ourselves if we aren’t in a “ready for a baby” place. Having a baby has to be on your time frame and your time frame only. No but, really. Do your best to ignore the pressure, even when it seems like it is coming from all angles, including surprising ones. Take my mom for instance. I never expected my mother, who has raised both of her children to be completely independent and career driven, to have such major grandma fever. I’ve am constantly hearing about how her friends on Facebook are sharing pictures of their grand kids, or how after 30 my eggs will be less viable, or how she’d like to be a young grandmother, etc…. And while she always prefaces it by saying she wants me to, “do it in the right order,” the inference is, I should get with the program.

But as we all know, it isn’t just coming from our moms. Babies are everywhere. They are all freaking over my Facebook, Instagram and Pinterest and they pop up in just about every conversation with my married friends. It’s enough to make any single lady want to freeze an egg or two…

But alas, I’ve realized that allowing all this baby fever to get to me isn’t helpful and all I can really do is focus on where I am at right now. Yes, I can absolutely picture a time where I will want nothing more out of life then to stay in on a Friday and sing my baby to sleep. BUT, if I really check myself, I can tell you there is no chance in hell that that time is now. Let’s look at the things that make me happy right now – shopping my ass off, weekends with friends, making out, the occasional party with celebrities, exercising like a maniac and kicking ass at work. Are these the hobbies of someone who is ready to be a mom? Nope. And that’s OK because that is where I am RIGHT NOW. So every time I start to feel the pressure, I just remind myself that just because others are in the “ready for a baby” place, doesn’t mean I have to be.

The second lesson I’ve learned is, don’t let your conflicted baby feelings make you stupid. I only just recently realized I was doing this, and the realization of just how dumb I was being totally freaked me out.

You see, over the last few years D and I stopped using condoms. Why? I have no idea. We never really discussed it and the switch was odd since we were both well aware of the fact that I am not on birth control. For awhile, my only real explanation is that we must both be morons. But a few months ago, I started to really question myself, and I realized that there was more to it.

You see, back in September, I was late. A good 3 weeks late. So late, that I actually told D about it and we had to have the, “what if I am pregnant?” talk. And so late that I had plenty of time to think of ALL the ways my life was about to change. What I realized is, there is no way I could handle being pregnant right now. But I also realized, that there was a teeny tiny part of me that would have been relieved if I was. Crazy, I know, but hear me out. Worrying that I may never get to be a mom causes me some pretty serious anxiety. And even though I don’t want a baby now, I suspect that I subconsciously thought an accidental pregnancy would at least mean I wouldn’t have to worry anymore…

As soon as I acknowledged this thought process, I was able to put the kibosh on the whole situation. While being pregnant now would relieve that anxiety – pretty sure having D’s baby would come with about 4,000 new reasons to be anxious. So, from that moment on, I vowed to have a more honest dialogue with myself regarding babies. Yes, I for sure want a baby in the next 10 years. But no, I do not want a baby now. And most importantly, I never want a baby with D.

So not only did I stop sleeping with D without a condom, I stopped sleeping with D altogether. Being honest with myself about my baby feelings gave me a lot of clarity and empowered me to keep my eye on the prize. If I do want to have a baby someday, then this is the time to be out, giving quality guys a chance… Not risking getting pregnant by a guy who I know doesn’t have the slightest desire to be a dad.

The bottom line is, when it comes to babies, there is still a lot I have to figure out. But the one thing I know for sure is, stressing about babies isn’t a problem us singles have to face alone. In fact, baby pressure is one of the few things singles, couples and marrieds can all empathize on, because no matter where you are on the path towards parenthood, you are feeling pressure until you pop one out. So when I feel the anxiety creeping up, I’ve discovered that I actually have a large pool of people I can talk to. And these people often understand exactly what I am feeling and usually make me feel pretty good about where I am in the present. Sometimes, that’s really all you need.

So that’s how I deal, but what about all of you? For the ladies out there, are you already feeling the pressure and do you have any tips on how to deal? And for my guy readers – do you guys get pressured too? I’d be super curious to know.

When you’re considering a giant life change you spend a LOT of time thinking about your future. And while I’m of course worried about what moving to NYC may mean for my career, my friendships, and my wardrobe; I’ve also thought quite a bit about what it might mean for my love life. When you feel like you’ve dated every eligible guy in your city, it’s only natural to wonder, will this move bring me any closer to finding “The One”?

Now I know many people roll their eyes at the term “The One” and hey, I totally get it. I’ve always been of the mindset that there are at least a handful of people with whom you could have a future with, and that it was all just a matter of timing. I mean really, if there is only ONE person for each of us, why is it that everyone from high school seems to keep marrying each other?? I have a hard time believing that the universe, in its infinite wisdom, threw so many soul mates together in one class. (And if that was the case, I’m fucked because I clearly let mine get away).

However, after spending the past 10 years dating, I am starting to doubt that there really are a number of people I could be compatible with for forever. Let’s look at the numbers shall we? Let’s assume I’ve met 10 thousand guys in the past 10 years (a rough estimate, but seems about right) and yet I have only been attracted to maybe a couple hundred. And of that subset, probably only about half of them were attracted to me. Then you start throwing in compatibility factors like lifestyle, where they live, religion, relationship status, future plans, morals, priorities, and one by one, every single one of these guys has been ruled out. It leaves a girl to think that perhaps there aren’t that many people with whom she could settle down with after all. Hell, maybe there isn’t even one…

This thought process generally leads to two lines of thinking for me:

1. Shit, I am going to die alone. I might as well have sex with D for now since he probably is as close to “The One” as I’ll ever get.

or 2. Maybe I need too lower my standards. (Choosing this option leads me to go on a slew of dates with guys I “should” like and yet never do… which generally brings me right back to option number one).

So last week, after yet another snore of a date, it was no surprise that I found myself beginning down this familiar road once again. And, then, just as I was debating which of my two unappealing choices I should resort too, I found some inspiration to hold out hope for something better. What brought about this shift? Allow me to share.

The first thing that inspired me was actually an episode of How I Met Your Mother… yes I find hope in TV sitcoms – so? In all seriousness, I love this show’s premise. The whole thing is about the dating failures of the main character (Ted) and how all of this ultimately leads to his happy ending. What single person in this world doesn’t hope that they too will be able to tell a similar story?

But I digress. The particular episode that stuck with me was the one where Ted goes on a blind date, only to discover that the woman is someone he was set up with 8 years before. They both (understandably) wonder if that means they’ve dated all the available people in NYC and thus try and see if there might be something between them. They re-live their first date, correcting one another’s  “mistakes” and laugh about how judgmental they were 8 years prior. And just as I was thinking that this episode was supposed to be a lesson in being more tolerant and open-minded in dating, the plot shifted. Ted points out that while they did have much more fun this second time around, they aren’t really a fit for one another. He tells her that they each deserve to be with people who not only tolerate their quirks, but love them.

I actually found this point to be quite profound. I am always beating myself up for not trying harder to like someone; but maybe, I need to just chill. Perhaps I am not being too harsh by waiting for someone I am truly excited about. Maybe it isn’t too much to ask for someone whose quirks are not only tolerable, but endearing.  If Ted can hold out for that person, so can I – right? (Just  go with it).

The second thing that gave me hope was that one of my best friends in this world got engaged. Now sometimes, when I see yet another engagement picture on Facebook, I catch myself becoming bitter, sad, cynical… the list goes on. But this time I felt nothing but sheer happiness and hope. You see, a couple of years back this wonderful woman and I were roommates and I got a front row seat for all of the shitty guy situations she went through. At the time, I could never understand it. It made no sense to me how a woman who was so beautiful, funny, smart and thoughtful could have such a hard time with the opposite sex. And since I was clearly no expert on dating, I often just hugged her, told her I knew in my gut she’d meet someone one day, and joined her for pizza/Sex and The City marathons. And lo and behold I was correct. A year and a half ago she met her fiance and in a totally unexpected way…

It all started back in April of 2011 when both she and I were recovering from semi-recent break ups and were in need of some fun. In hopes of blowing off some steam, I accepted an invitation to a bar crawl from another San Diego dating blogger. Now I had never met this dude or any of his friends, but I figured what the hell. He’s a funny writer, he can’t be so bad :) And so I roped my dear roomie/partner in crime into going with me. I distinctly remember convincing her by saying, “You never know, maybe you’ll meet your future husband.” (a thought which made us both laugh considering a pub crawl in PB seemed like a pretty unlikely place to meet one’s future husband). But as luck would have it, that’s exactly what happened and now she couldn’t be happier. (You’re welcome, Kel ;)).

Looking back, there is no way we could have known that all that bullshit she went through was leading her here, but it was. Which makes me think that hopefullly, some day, I will look back on all the crap with D, Mr. Not Quite Right, Mr. Cute But Whiny and all the others, and realize it was all just a part of my journey towards My Guy. Now that’s an encouraging thought!

SO, I’ve decided to remain hopeful that there is someone out there (even if I don’t have the slightest clue who he may be). And while it looks increasingly unlikely that I am going to meet my special someone in San Diego, perhaps this move to NY will hold promise for me. Or maybe that move will bring me somewhere else that ultimately leads me to this guy – who can tell? But since I truly can’t predict the future, I might as well try and stop stressing about it. Instead I am going to work on not doubting myself  in the present and try to just enjoy the ride. I know one thing for certain, when I do finally meet My Guy, I sure as heck will have a lot to look back and laugh about.

I just returned from a business trip to New York, and I gotta tell you, I was heartbroken to leave. I love everything about that city (including all the men in suits!) and I always leave thinking – why the hell am I living in boring old San Diego? If I didn’t, would my love life be different? Could my dating problem be as simple as - I live in the wrong city?

I’ve been obsessing about this thought for awhile now and before you dismiss it, hear me out. I know the guys in New York are by no means perfect, but heck, they are different. I would welcome a whole new set of challenges because at least it would be a break from feeling like I am hitting the same walls over and over. Plus, if I may be frank, it seems like New York attracts a much larger pool of smart/motivated gentleman than good ol’, laid back San Diego.

I know, I know, that’s a major generalization… I have absolutely known smart, ambitious guys in San Diego. However, these guys are few and far between, and even some of the most successful still suffer from a serious case of Peter Pan (I never want to grow up) syndrome. I mean, how can you really blame them? San Diego’s gorgeous weather, beautiful people, and the constant influx of visitors make it a natural party town. And who would want to work a 9-5 when you could spend all day at the beach, surfing and drinking brewskis?

But while I truly respect that lifestyle (and frankly am sometimes jealous of it) it generally makes dating someone like me hard. I either get frustrated with the fact that said gentleman always wants to party on  a Wednesday when I have a big presentation in the morning. OR (and this one is much worse) the guy develops a weird inferiority complex about dating someone more “successful” than him.

Mr. Not Quite Right was the prime example of this. I was head over heels for the guy. I thought he was the perfect balance of smart and fun and I was so proud of him for getting a career in an industry he was passionate about. But he was obsessed with pointing out how much smarter I was, how much money I made,  how I went to a better school and on and on. I can tell you, that wasn’t fun.

And sadly, this situation with Mr. Not Quite Right was not an isolated incident. I have noticed it in varying degrees with a lot of the guys I’ve dated and, quite simply, that sucks. I’d love to date a guy who looks at my professional success and thinks well that’s rad – this chick  can keep up with me! She loves what she does and is good at it. How sexy.

Obviously a guy like this is going to be hard to find anywhere I go. But my theory is that a more business-oriented city would likely attract this type of gentleman. At least, that’s the hope…In any case, a larger pool of driven, “successful” men isn’t the only appeal to moving to New York.

Another compelling reason for the move would be the distance it would put between me and San Diego and thus between me and D. According to Google Maps, Manhattan is  a whopping 2,755 miles away from D. Kinda makes those impulsive late night visits a bit less likley, right? And while I absolutely know I need to work on getting over D without putting things like distance between us, I also know it wil be a lot easier for me to move on when he isn’t right down the street.

But most importantly, I think this move could be a much needed “attitude re-set” for me.  I feel so beaten down by my experiences with D, Mr. Cute but Whiny, Mr. Not Quite Right, The Texter and of course, glorious Brad, that I am just not sure I have it in me to be optimistic about any guy in San Diego right now. But guys in NY? Well they’re a different breed! There may still hope there.

All that being said, I have to admit that I have my concerns about moving as well. I can’t help but think, what if I move all the way to New York just to repeat all the same mistakes as I made here? Then I’ve wasted a whole lotta time, money and energy for nothing – and that’s not what you want.

So, in order to avoid this situation, I have come to terms with the fact that I have a lot of work to do before I make any cross-country moves. First, I  need to find enough self confidence to realize that I deserve so much better than the D’s of the world. Second, I have to learn to be a bit more forgiving and empathetic of guys (and probably myself!). And third, I most certainly need to work on putting myself out there with a guy I am dating in the same way I put myself out there with all of you. Without taking all of these steps, I am sure I’ll just end up with a New York version of D and a lot more heartbreak.

And while putting these “goals” in writing is one thing, actually accomplishing them is going to be a whole lot harder. I’m going to need help. Help from my family, from my friends, from all of you and from a professional. So, in the hopes of getting my head in an awesome place before moving, I have officially decided to start chatting with a therapist. I plan to take the next 6 months to work on “me” and then if I feel like I am in a better place personally, I’ll pack my bags for New York because heck, at the very least it will be a fun adventure. I am single and now in my late twenties. If I don’t do this now, I never will. And I certainly don’t want to be 40, single and sitting around with my 5 dogs wondering, what could have been if I had moved to NY…

I’ll of course keep you all posted on how this progresses, but in the meantime wish me luck on my little self journey. Oh and if any of you lovely readers happen to be located in NYC, holler at me. I am sure as heck going to need some friends when I get there!

So, this week I turn 27. Yes, 27. Do you realize how old that is?? It is “late twenties” old.

Yikes.

And although I’m never a fan of getting older and more wrinkly, I’ve been dreading this particular birthday for awhile… You see, for as long as I can remember, I assumed I’d get married at 27. Well clearly that’s  not happening and now I not only feel old, but I also feel like an under-achiever.

Of course, I know what most of you will say – “Oh get over it… you can’t plan your life! 27 is young! Yada yada…” And you know what, I completely agree with you. But that doesn’t make this milestone any less hard to swallow. I can’t help but feel, well, icky.

As I was expressing this sentiment to my boss (we’re tight like that) she mentioned she had a similar experience with her own milestone year. She said at the time her sister told her to stop looking at the birthday as a report card and start thinking of it as a progress report. So you aren’t where you want to be? What are you going to do to change it?

I mulled over her advice for a bit and decided I liked it. It’s not like life is over at 27! I have plenty of time to make changes. So I shall.

And the good news is, when it comes to dating, I am already well aware of some changes I can make. In fact, I am well aware of a LOT of changes I can make. So in honor of my 27th birthday, here is a list of 27 things I’ve learned about dating this past year. Perhaps by applying the below lessons, I’ll be able to move forward in the dating world and maybe, just maybe, this will be the year I fall in love.

27 Dating Lessons

1. Once a cheater, always a cheater. Walk away from these people – quickly.

2. Lot’s of people are afraid of facing their fears (dating or otherwise) and there is no shame in admitting your afraid.

3. Guys can be full of shit. Not all guys, but some, and I won’t be forgetting that lesson again anytime soon.

4. If you are in a dating rut, quitting isn’t always the answer. Try doing something different. Shake things up… who knows what will happen.

5. No one thinks I should be with D… I hear ya peeps, I do. And I am working on it.

6. You can’t judge yourself for your past dating mistakes. All that does is make you feel like shit, and often feeling like shit just makes you commit more mistakes. Damn cycle.

7. It’s hard to ignore really hot sex. BUT hot sex, does not a relationship make. Too bad!

8. There are a lot of guys who don’t know crap about writing a good online dating email and it is not worth it to let every “heeeeeyyy sexy girrrrl!!!” depress you.

9. Plans don’t always pan out. See the top of this post.

10. Everyone wants different things out of a relationship. What works for you may not be the type of relationship that works for your friends (or your blog readers). Don’t worry about what others think or do, and if you are happy, go with it. It’s your journey.

11. Just because a guy isn’t wearing a wedding ring, doesn’t  mean he isn’t married. Sigh.

12. The only really good way to avoid looking like a jealous bitch is to not hang out with people who will make you jealous. Period.

13. Despite the fact that most girls seem to share the same sentiment about the rampant over-use of emoticons, there seems to be a few passionate guys defending them. Ladies, I guess we are just going to have to learn to deal?

14. If you have a bite mark on your leg, there is no way to convince someone that said bruise is anything other than a bite mark.

15. There is a fine line between taking it slow and taking it nowhere. To avoid the latter, stay out of “friendly” hang outs in the beginning and never, ever, discuss taking it up the ass.

16. Girls sometimes obsess so much over whether a guy likes them that they forget to ask themselves about how they are feeling. This is not beneficial for anyone. Don’t do it.

17. Being good on paper doesn’t mean shit. Again, sigh.

18. While you do sometimes have to play the game, there are definitely times in dating where being direct and cutting the bullshit will make your life a lot easier.

19. Changing your number will not stop you from calling someone you want to call.

20. If someone is leading on their best friend, that should be a red flag. This person is someone who really likes his/her ego-petted and isn’t afraid to “use someone” to get it done.

21. It is extremely hard to be open to meeting someone new if you are still hung up on someone from your past.

22. Free online dating isn’t all bad. While I doubt I’ll ever try Plenty of Fish again, I actually had an OK experience on OK Cupid. (Pun intended).

23. A guy who is confident and in control is automatically much hotter. I am going to continue to look for these elusive males.

24. Sometimes, the phase out is the way to go. I know some of you weren’t so thrilled with this plan, but I gotta say, it has been effective a few times in the past year. It still works!

25. We all have days where we think we are going to die alone. AND these days pass…

26. Stay away from guys named Brad – I have kissed 2 guys named Brad and both disappeared on me. Brad = bad.

27. Girls can be bat-shit crazy. Sometimes it is easy to blame the dudes for the disaster that is dating in your twenties, but the truth is, we’re all guilty. We confuse guys, we demand a lot, and sometimes, we are just flat out crazy. It’s best to keep that in mind when dating and throw the guy a bone every now and then. It’s rough out there for everyone.

So there you have it… I think I am officially ready to enter my 27th year of life now. Bring it on love. I am ready for you!

Okkkk guys, lets talk about text messaging again, shall we? It has been over a year since our last chat on the subject, and unfortunately, the situation appears to be getting worse…

Listen, I have come to accept that text messaging is the only form of communication the male species likes to use. And although I still stand by what I said in our last talk (that there are, gasp, times where picking up the phone is more appropriate) I have learned to appreciate a quality text or two. In fact, I’ve found that a witty text banter can give you a lot of insight into the chemistry you might have with a fella and, in some cases, texting can even serve as some quality foreplay. However, this is only when the texting is executed correctly – which, it is so often, not.

So, my gentleman friends, I share the following list of texting pet peeves with you in love because I know you are not committing these faux pas with malicious intentions. Most likely you are completely unaware that these are even somewhat irksome. Therefore, in order to help you keep on the good side of these tricky females you are pursuing, here are a few more texting kinks I think we should work through.

1. Starting every text convo in the exact same (boring) way.

If every text conversation you send me begins with  ”Hey how’s it going?” I get stressed because there is no creative response to such a blah question. What can my response be other than, “Going good! How are you?” which is just as uninteresting as the original question. I want our text conversations to have some spice! Let’s be a bit more creative with our openers, shall we?

Besides, in the instance where something is really wrong, it is not real likely that I am going to start texting you my whole sob story. So instead, I am forced to lie and just go with “everything’s great!” because texting you about my grandpa’s death would just be depressing.

2. Waiting forever to text me back

I really don’t get when you guys text, I write back, and then you wait a good 30 mins to write back again. Hi, you JUST wrote me. What the hell? Is this some sort of weird game playing thing? Do you really think that I think you are super busy and thus unable to write me back? And if this isn’t a good time, why did you text me in the first place? eesh.

I like my text conversations to have a nice flow. If we are dragging a text conversation out over multiple hours, I promise you, I’ve lost interest.

3.Texting me for an extended period of time before I’ve ever met you or heard your voice

I can’t even pretend to understand the guys that do this. Dear sir, you want a pen pal, not a girlfriend…

I once met a guy on Match who texted me for an entire month without asking me out. I had never head the guy’s voice but I knew all about the time he spent back east over the holidays, the sweater his mom bought him for Christmas, and the weekend of fun he had when his college friends were in town. Dude, I don’t care. If we aren’t friends and we are never going to meet, there is no way I am interested in daily texts from you.

Needless to say, when I switched my phone number, I forgot to tell him.

4. Asking for a picture.

Yes, that kind of picture. Apparently, this is not that uncommon these days as I’ve asked around and many of my friends have received similar requests.

Hey guys, this one is pretty simple… unless we are in a super serious relationship and I trust you completely, there is no chance in hell that I am sending you a picture like that. So don’t bother asking!

Ya gotta see it from my point of view. I am a respected business woman with an easily google-able name. If that shit ended up on the Internet I would die. No literally, I would curl up in a ball and die. So if you and I just started dating, or we aren’t exclusive (D, I am looking at you…), asking me to send you a picture is awkward. Then I have to feel like a total square when I turn you down, and I do not appreciate that.

5. Being a text stalker

Buddy, if I haven’t responded to your last few texts, that is not code for, “please keep texting me.”  And just so you know, waiting a few days/weeks/months in between each text doesn’t make me any more inclined to respond. Read the signs. I am not answering = I’m not interested. Perhaps if you had called in the first place, I would have been. :)

6. Deep conversations via text

Call me crazy, but I’d really prefer not to have some deep conversation about “us” or any other serious matter via text. If you absolutely can’t make it happen in person, then at least pick up the phone. The chances of all parties understanding the takeaways from said conversation go up like 100-fold. No one likes a misunderstanding.

7. Apology texts

By far my biggest texting pet peeve is the,  ”I’m sorry texts.” You know what, I am sorry too. I am sorry that I have to include this in this list, because to me it is so darn obvious that if you are saying you are sorry you should be picking up the phone. My absolute favorite offender of this was dear Brad, who cancelled dinner on me via text and then had the nerve to apologize for not calling. Puhlease. Do not, do not, do not, say your sorry via text message.

So there you have it, guys, just a few pitfalls to watch out for if you are a text-happy gentleman. I think us females have really come a long way in our appreciation and tolerance of texting, but I beg of you, meet us half way. In return, we’ll work on initiating the text conversation more often so that you don’t have to do all the heavy lifting.  Sound like a deal?

My behavior this week has not been, um, my classiest. OK, it hasn’t been classy at all. In fact, the choices I made this week very much reminded me of what I oh-so-fondly refer to as my “slutty phase” during the 18th year of my life.

You see, this past week, I may or may not have slept with 2 different guys, 2 nights in a row. I know, yeesh. Mind you, they are both guys I’ve slept with many times before and who I know very very well, but that didn’t make it any less awkward to explain the bite mark on my thigh to gentleman #2…

But here’s the thing, even though I didn’t practice much (/any) self control this week , I don’t feel the least bit bad about it. I know I probably should. I probably should be kicking myself for being so impulsive and horny – but I’m not. And that makes me wonder… am I a slut?

Now, I know everyone had a very different opinion as to what makes someone slutty, but there seem to be a few reoccurring ways that people measure sluttiness. These include the following:

• Your number of partners
• Your willingness to do “dirty” things in the bedroom
• The number of one night stands you’ve had
• The way you dress

While I see why people look to these four factors to determine sluttiness, I actually don’t think any of this is particularly relevant. In my opinion, these traditional ways at categorizing someone as a slut negate a few key factors and are often looked at out of context. Allow me to explain…

Let’s start with the people who judge someone’s level of sluttiness based on the number of people they’ve slept with. I think this is an extremely flawed strategy for 2 reasons -1. There is no one standard for what “number” makes you a slut. Is it double digits? Anything above 20? Different for guys and girl? Who can tell.

And 2. The number means nothing without context. For example, let’s pretend you’ve only slept with 5 people BUT those 5 people are the only people in the entire world you could get to sleep with you. That means you’ve slept with 100 percent of your opportunities. On the other hand, say you’ve slept with 13 guys but have had a 100 opportunities to have sex. This would make you much more discerning, despite having a larger overall “number.”

I feel that if we are going to gauge a person’s sluttiness using a number, than it should at least be the proportion of their number to their potential number.

As for the people who think being “scandalous” in the bedroom makes you a slut, I am going to have to go ahead and disagree with that too. There is an infamous “Cali and D” story from back when I was 17 where I gave young D head in the walk-in fridge. For years I cringed at that memory, thinking eek, what a slutty and naive thing to do. But now, as I have matured and grown comfortable with my sexuality, I’ve realized that that incident, was actually just me enjoying sex. I’ve always liked taboo things in the bedroom and love the “I have to have you now” feeling. And the truth is, I wasn’t giving him a bj in the walk-in because I was insecure or felt pressured into it – it was because I thought he was hot as hell, I wanted to, and I thought it was fun to get him off.

9 years later D is still pushing my boundaries in the bedroom and I don’t have a single regret about the things I’ve tried with him. They are often surprisingly enjoyable and being adventuresome has increased the level of intimacy between us 100-fold. I hardly think that being willing to experiment and spice things up makes me a slut, even if D isn’t my significant other.

Now, I do sort of understand those who look at the number of one night stands as an indication of sluttiness, but again I think this number has to be qualified. I see a big difference in the “oh I hooked up with my friend only once” and” I just slept with a random at a bar.” For instance, out of the 13 guys I’ve slept with in the past 9 years, technically 4 of them were one night stands. But of those 4, they were all friends of mine and people I knew a lot about prior to jumping into bed with them. In fact, one was my best friend/roomie, one was someone I’d made out with a few times before and another was a guy I dated for a month. So sure, I only slept with each of them once, but I am hardly running around sleeping with strangers. (Perhaps I’d have better luck if I was!)

And finally, to judge someone by how they dress is just silly. Some of the prudest girls I know wear the lowest cut shirts and the shortest skirts. And while I did behave pretty slut-like this week, I did it while wearing teal jeans and a long sleeve blouse. How you dress is simply a form of self expression and has no correlation with the likelihood that you’ll get naked. Anyone who says otherwise is just wrong.

The truth is, I do think there are a few things that qualify a girls’ behavior as slutty, but they aren’t these things listed above. To me, sleeping with someone you don’t like/aren’t attracted to just to have some attention for the night - is pretty darn slutty. I also think it is slutty to prioritize sex over everything else. Those girls who will put “getting laid” above their friendships, relationships and general morals, tend to cross that slutty line. And finally, girls who have no problem routinely dropping their pants on the first date… OK kinda slutty.

But the key here is I rarely think a girl is a slut. I think she may behave slutty for a certain period of time for any number of reasons (low self-esteem, too much life stress, rebelling, because she can, a genuine love for sex) but I refuse to believe that these actions or this time period then defines her. I think within each and every one of us there is a slut and an angel and I, for one, am glad I have made room for both of them throughout my life.

So that’s what I think. Now I’m curious – what is your take? What makes someone a slut or what behavior do you classify as slutty?

If you’ve ever dabbled in online dating, you’ve absolutely hit the online dating wall at least once or twice.  It’s inevitable. After a few months on a dating site, the excitement of getting emails every day from aspiring boyfriends has long since worn off. You’ve likely gone on a few dinner dates and perhaps found, le sigh, you’ve got zero chemistry with any of these people. And eventually you start to feel like there’s no point in even opening that message from “bigboy69” because, let’s be real, it’s just going to say something dumb.

Trust me guys, I am well aware of what it feels like to be in this place. I have hit the online dating wall many, many times. And in the past, I’ve always just cancelled my subscription and prayed that I’d start meeting people in the real world sometime soon. As you well know, that’s worked out swimmingly…

So this last time, upon deciding that quitting isn’t the most awesome strategy, I decided to switch things up. Instead of cancelling my Match subscription, I decided to get creative with some new tactics. And ya know what, I just met a pretty cool guy (but I’ll write more about that once I see how that goes).

Now you’re likely wondering what these effective creative tactics were. Well I’m glad you asked. Below are my new tips on how to cope with hitting the online dating wall without just throwing in the towel.

Search with a friend – It is easy to grow fatigued after looking through so many profiles and, eventually, you may to find that every dude just starts to look the same. When this happens to me, I find myself scrolling without really looking, and I am obviously never going to notice a cool guy if I am not at least paying attention!

So if this happens to you, bring a friend over to peruse with you. They can point out fellows you may have overlooked or laugh with you at the insanity that is some profiles. They can also help you with the people you are on the fence about by telling you when you are being dumb or when you would be settling. Plus, if you do happen to like a guy you found while browsing with your friend, that’ll make for a fun story.

Switch up the site – I know awhile back I wrote about free online dating sites and I wasn’t so into them. However, upon hitting my most recent online dating wall, I decided to give OKCupid just one more chance. I mean heck, one of my closest friends is marrying someone she met on there – perhaps I should be a bit more open minded.

The good thing is, being on a new site is always exciting at first. New people, new site features, lots of fun questions to answers… So I dove in and let’s just say I am glad I did. The aforementioned new guy was someone I met on the site.

Re-do your own profile – Maybe you haven’t attracted anyone you are interested in because of what you’ve put out. I’m not saying that anything you wrote was wrong, but perhaps switching it up will attract the type of guy you would be more interested in responding too. It obviously couldn’t hurt to try.

Start responding to people – Online dating is never going to get more exciting if you are ignoring every message. And while I’ll never be one to recommend responding to a guy you know you could never like, I do think it can help you get out of your dating funk to give someone a chance. Even if it doesn’t work out with that guy, just getting back into the whole “responding” act may open new opportunities for you. Take my sister as an example. Mini  Bradshaw has been testing the waters of online dating for a few months now and was just about to throw in the towel when she agreed to go on one more date. And while she didn’t actually like that guy at all (she in fact referred to him as an “uber goober”) she did run into another guy she knew on her way to the bathroom. And now, she’s got a date planned with that fine gentleman.

Change your search parameters - Perhaps you’ve been way to picky and you need to be a bit more open in your searches. Just like in the real world, sometimes you gotta ditch the checklist.

OR maybe you are being a bit too open and it is time to be a bit more specific. It gets depressing to scroll through page after page without seeing a single guy who catches your eye. So give your eyes a break and try being picky.

Mock people’s dorky profiles via FB updates, tweets and blog posts – Ok so you haven’t found a love connection just yet, but you have to admit, there are some good laughs to be had from reading peoples; profiles. So while you are waiting for someone awesome to come along, feel free to share the humorous anecdotes with your closest friends (and/or everyone on the internet). It makes everything seem a little less serious.

Search other cities – So there aren’t any smart, nice, hotties in your city? Good news, there are a ton of other cities. When I was bored a few weeks ago my friend convinced me to start looking at guys in SF. Oh holy heck, there were some adorable guys there. And no, I am not moving to SF, nor am I interested in starting up some sort of long distance relationship, but it sure was fun to imagine. Seeing the cuties in SF reminded me that I have not, in fact, dated every guy in the world, and that I don’t need to give up hope just yet.

Take a break - If all else fails, don’t keep hitting your head against a wall. You don’t want to be at that point where you are forcing yourself to go on dates and are repelling guys with your “nothing ever works out!” attitude. The truth is, while you don’t want to give up at the first sight of the online dating wall, there are going to be times where no amount of tips or tricks will change how you are feeling. At those times, taking a short break may be just what the doctor ordered. And who knows, maybe you’ll have better luck than I out in the real world.

I’ve been postponing this post for a long time because, let’s be real, cheating isn’t a fun topic. It’s horrible and awkward and frankly, something we’d all like to pretend doesn’t happen nearly as often as it actually does. But the truth is it’s a reality in this complex world of dating and the time has come to talk about it.

Over the years I’ve unfortunately had a fair amount of experience with cheaters (a fact that I really and truly hate). However, all this experience has taught me a whole heck of a lot and, thus, I’ve compiled a list below of everything I’ve learned. Now these are just my opinions and I know everyone has very personal beliefs when it comes to cheating, so please feel free to add any of your own thoughts in the comments.

Eight facts about cheating and cheaters

1. Lots of people cheat (not just “bad” people) – Sure it would be lovely if only major assholes were cheaters but, in my experience, that just isn’t the case. I’ve known genuinely quality guys who cheat. And while I’ll never understand how these guys can be a caring, sweet, smart, thoughtful and also cheaters; I’ve learned to accept that sometimes that is the case. That being said, I certainly wouldn’t want to date someone I knew to be a cheater – regardless of their other positive attributes.

2.If you are cheating, you are not in love – Nothing grates me more than a guy who cheats repeatedly and still claims to love his girlfriend. Listen up people – if you truly love someone, you would never, ever disrespect them that way. You would never do something that could crush their heart and make them feel like such an idiot.

I’ve seen guys who are truly in love and who have been put in a position where it would be really easy to cheat (hot girl, lots of alcohol, sexual tension)… and ya know what, these guys pass the test every freaking time. It really is as simple as that.

3. Some people seem to think that if it isn’t sex, it isn’t cheating - Um, false. Cheating is cheating. I don’t care if you stick it in just a little, if you don’t finish, if you don’t make out or whatever variety of the “it’s not cheating if…” excuses. Every single one is bullshit. There is NO girl I know who would be like, oh hey no big deal that you just got a blow job from your ex-girlfriend. Just because you didn’t get the girl you are hooking up with off, does not make it any less deceitful. All it does is make you shitty in bed.

4. People rarely cheat just once – I don’t think I know a single person who has only cheated once. I wish I could say I did, but I don’t. Maybe it’s one of those things that once you cross that line and get away with it, you can’t help but cross it again. I don’t know, I’ve never cheated. But seems to me like most the people I know who cheated, never told their significant others, never got caught, and then did it again. And again. And again.

5. Girls who find out they were cheated on often go batshit crazy and blame the other girl rather than the guy – One time, back when I was 20, I found out that the gorgeous guy I hooked up with over the summer had still been dating his high school sweetheart at the time of our steamy night. This revelation sucked as I actually really liked this girl. She and I had been cheerleaders together and she was one of my roomie’s best friends. So as soon as I learned the truth, I called up the dude and told him he needed to tell her, or I would. I thought it was the right thing to do (especially since he and I had hooked up before).

So he told her and then I spent the next week getting daily messages about how awful I was and warnings that if she ever saw me in San Diego, I better run away. She called me every name in the book, told me I had ruined her life, and quite honestly, made me cry. And after I aplogized again and again, and told her that I hadn’t known they were together, etc., I finally gave up and realized she was a nut. (A fact that was confirmed when she then decided to stay with him).

While I am sure some girls out there would handle this information in a more mature manner, I’ve never been inclined to test that theory.

6. Being the other girl always makes you feel like shit – As you all know, I am just as prone to making mistakes as the next person. And one of my least favorite mistakes has been knowingly helping a guy cheat on his girlfriend. Please believe, on the occasions that I have made this choice, I’ve always felt plenty justified at the time. I told myself… I love him. He was mine first. She watched him kiss me and stayed with him, so clearly she’s a moron. I was drunk/horny… blah blah blah. But you know what, it doesn’t matter how validated you feel in the moment – afterwards, you inevitably feel like shit. The best case scenario only leaves you feeling used and guilty. But in the occasion where you have genuine feelings for the guy you are helping cheat, the hurt is so much worse.

7. No one thinks their boyfriend or girlfriend is a cheater - Now to all my happy, “in a relationship” readers, please do not take offense to this. I am in no way saying that everyone is a cheater. I am simply saying that I don’t know any of the girls who have been cheated on who have been like, oh yes, I think my boyfriend is totally capable of cheating. Instead, there they are, writing “I love you messages” on Facebook while he is off getting naked with someone else.

And finally/most importantly…

8. If someone is hooking up with you while in a relationship with someone else, they don’t give two shits about you – This guy/girl is not your friend. A friend wouldn’t put you in a position to feel used and embarrassed. Period. Every time they say, “I don’t want to hurt you” or “I like you” it is really just code for “please don’t tell my girlfriend…” The truth is, the only person a cheater cares about is himself. So stop trying to figure out why they’ve decided to cheat, or what it all means (who cares?) and cut then out of your life. Cheaters suck and you would be much better off without them. End of story.

So there you have it. Those are the eight lessons I have had to learn the hard way about cheating. Now you go… any pearls of wisdom you can add?