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What to Ask Before You Hook-Up With Your Bestie

23 Apr

So, I have a bit of a bad habit of hooking up with my best guy friends. (I know I’m not alone on this one…) Bestie hook-ups are just one of those things that always seem to happen between friends of the opposite sex – no matter how sure you are that it never will.

Over the years I have hooked up with 3 of my best guy friends with a variety of results. With Mr. Tall, it was pretty much a disaster. We don’t speak of it, and frankly, these days, we just don’t speak. With Ad Dude, it was confusing at first, then a disaster, and then eventually, just fine. And with My Bestie, it has been actually quite perfect. No drama, no awkwardness and lots of fun.

Since My. Bestie is coming to town this week (yaaay!) it got me thinking about what one should consider before hooking up with their best friend. Ladies, if you want to avoid awkwardness here are a few things to consider before you cross that line.

1. Why does he want to cross the line? If the answer is: he’s super hammered and you just happen to be there — don’t do it. You are risking your friendship, and besides, it probably won’t be a good hookup. If you think there is something more to it and that perhaps he’s been wanting to “cross the line” for sometime but wasn’t sure how, then perhaps it is something worth considering.

2. How drunk are you? You’ve already assessed his level of drunkness (see above) but make sure you check yourself. If you are blasted out of your mind, he’s going to feel all awkward about “taking advantage” of his best girl friend and think that you probably didn’t mean to hook up with him. His insecurity will breed awkwardness, I promise.

3. Is he in a good place in his life? As his best friend, you’ll certainly know if he is in the middle of some existential life crisis. If he is in between jobs, questioning the meaning of life, and just generally down in the dumps, this is not an opportune time to test out these waters.

4. How does he act about other girls he hooks up with? Before Mr. Tall and I crossed the line, I was privy to many-a-convo about the silly girls he hooked up with. Not to make him sound like an ass, but these conversations should have been a clue to me that he has no problem with hooking up with a girl he doesn’t intend to date. Of course, like most girls, I convinced myself it would be different with me, because we were best friends and he had too much respect for me to treat me like that. And like most girls, I was wrong.

5. How close are you? This is a double edge sword. On one hand if you are super close you can call him on his bullshit if he starts to act weird. On the other hand, if you are super close, you have more to lose if your friendship goes down the tubes.

6. How long have you been friends? My Bestie and I have been friends for 10 years and we waited 8 years before crossing that line. On the other hand, with both Mr. Tall and Ad Dude, we were only friends for a few months when something happened. This was a result of the fact that we were spending a LOT of time together as friends. In fact, I even lived with Mr. Tall and I worked with both of them (sorry co-workers who read this blog for that over-share). At the time, it seemed natural that these friendships progressed so quickly but in hindsight, I wish I had waited to explore that territory. I’ve since realized that the longer you have been friends, the better foundation you have, and the better you can handle the inevitable awkwardness of the hook-up situation.

7. Have you talked about this as a possibility before? While My Bestie and I waited 8 years to cross the line, we’d been talking about doing it for at least 5 years prior. By talking about it for so long beforehand, it made it clear to both of us that this wasn’t something that was just accidentally happening, which is probably why it was never weird or different. On the other hand, with Mr. Tall we also talked about it before hand but in the context of how it would never happen. You see, Mr. Not Quite Right was uber-jealous of Mr. Tall, so much so, that Mr. Tall was actually the subject of our final fight. I, of course, told Mr. Tall this, and he protested that this was ridiculous because “we were just friends.” A whole week later I woke up at his house. And judging by the aftermath of this hook-up, his denial that he had a crush on me should have been a clue I paid a bit more attention to.

8. What do you want out of it? Could you see yourself dating your best friend? If so, you better be darn sure he is on the same page before anything happens. If you want to date him and he doesn’t want to date you, that will hurt like hell. Then you get to deal with being rejected and losing a bestie in one swoop. Good times

9. Where does he live? This may seem silly, but part of the reason I think things worked out so well with me and My Bestie is that he lives in Colorado – much too far for me to actually try and date him. This way, we can both pretend that we’d be dating if we lived closer (even though I’m pretty sure we wouldn’t) and no ones’ feelings get hurt. The same was true for Ad Dude. Things were pretty awkward between us for a long while – right up until he decided to move back to Minnesota. From that point on everything was fine, because there was no pressure or wondering, “why aren’t we dating?”

At the end of the day, the bestie hook-up is a complicated but common situation — approach it cautiously and with care. When it works out, it is perfect. But when it sucks, it is downright disastrous. Most importantly, keep in mind that if the bestie hook-up does result in you losing a friend, well then he wasn’t really a good friend anyway.

26 Responses to “What to Ask Before You Hook-Up With Your Bestie”

  1. Kelsey April 23, 2011 at 4:21 pm #

    I can relate so well to hooking up with friends…. with my limited 17 years experience, which means I choose to go no farther than making out, it makes it much, much easier to stay friends.
    I guess my point is the farther you go, the harder it is to stay on a normal level. Does that make any sense? Haha.
    Thanks for the advice, it’s great as always :)

    • Cali Bradshaw April 25, 2011 at 5:01 am #

      Thanks Kelsey! So glad you are finding the posts relevant :) You are actually quite right tho. Regardless of age, it is much easier to stay friends if all you did was make out. Good point!

      Thanks for reading, Kelsey!

  2. Ripper April 24, 2011 at 1:43 am #

    1. GFU!(good for u) I just made up that acronym.

    2.”This way, we can both pretend that we’d be dating if we lived closer (even though I’m pretty sure we wouldn’t) and no ones’ feelings get hurt.”

    hahaha thats funny. Story of my life!

    “Super Hammered” “Blasted out of your mind” haha you sound like fun

    As far as besties go, and yes I feel gay saying the word besties, it IS a double edged sword and not really worth it if you value the friendship.

    cheerio

    • Cali Bradshaw April 25, 2011 at 4:57 am #

      1. I love acronyms, so thank you.

      2. Haha thanks. Story of my life too…

      Yes, occasionally I can be a good time. And, yes two out of my three bestie hook ups happened on nights where I had been over-served so I think this is an important question to ask. You are right though, it really isn’t worth it if you value the friendship. At the very least, it will make things very uncomfortable for a while….

      Thanks for the comment!

  3. Jessica April 25, 2011 at 3:01 pm #

    I’m currently going through this with my best guy friend. We made out in middle school and it meant nothing…until it did, 6 years later when we hooked up again. I failed at realizing #8 above until it was too late. It was all supposed to be fun but then I realized I wanted more. That was 4 years ago and I’ve pretty much been in love with him ever since – it totally blows.

    I’m moving to California (from Philadelphia) in 4 months, so I hope that it gets easier, the way you explained in #9. Knowing us, I have a feeling we’ll talk like we are dating, because it will be easy to do when no actual follow-through is required. We’re all talk…

    Thanks for the advice!!

    • Cali Bradshaw April 26, 2011 at 12:53 am #

      You are most welcome, Jessica and I hope your big move does help! Nothing sucks more than being in love with your guy friend… I’ve been there! It blows. Good luck to you!

      -Cali

  4. nese April 26, 2011 at 5:07 am #

    lost a best friend of 5 years due to the bestie hook up :( be careful!!

    (cal, you know who i’m talking about!)

    • Cali Bradshaw April 27, 2011 at 1:21 am #

      I do :( And I still think that he sucked for that. But yes, your warning is a good one for all… bestie hook-ups are not a joke!

      Thanks for reading, Nese.

  5. VicT April 27, 2011 at 6:14 pm #

    Well you know where I stand on women and men being friends. The fact that we have all had hook ups with our besties kinda proves, that we always want more (by we I mean either us or them).

    I agree with the advice. Also, I think that we are fooling ourselves if we think that a guy is just a friend and we end up hooking up with them. I feel like EVERY time this has happened to me I have started to either get suspicious that they liked me, or have kinda liked them already.

    I would only add, is that if you do end up hooking up with a guy friend and you want to end it. There are two ways to handle it.

    1) If the hook up was a one time occurance, just go on as if nothing. Don’t bring it up unless he does. And just continue acting like you did before hand.

    2) If the hook up has been a regular occurance and you want it to end. You will need to to take a few steps back from the friendship. This is just temporary, but we all need some cool off time to let things go back to “normal”

    • Cali Bradshaw April 29, 2011 at 8:48 pm #

      Thanks for the comment, Vic, and yes you are right. It does seem like the vast majority of the time, someone wants more. Love your advice about how to handle it… It is SO hard for me to not bring it up though, especially to our other friends. With Mr. Tall, I ended up spilling the beans to one of our other best guy friends, only to find out, he had already to him!

      Thanks for the read! Cali

  6. vegas girl May 2, 2011 at 3:10 am #

    I am currently in an ongoing situation of hooking up with a guy friend. So crazy, but we actually met because I dated one of his friends 4 years ago. Yes, we all still talk and hang out. On top of that, I am his best friend’s roommate, so after we hooked up there was a few weeks where I was mad at myself thinking that I just screwed up big time all over a few shots of vodka. Well it’s been 4 months now, and I slowly went from thinking it was a mistake, to being in love.
    So sometimes it can work out…. =)

    • Cali Bradshaw May 10, 2011 at 4:36 am #

      Great insight! Yes, it definitely can work out sometimes. I suppose it all just depends on timing! Thanks for the comment.

      -Cali

  7. Sarah July 25, 2011 at 3:24 am #

    HAHA,I love all of your advice, it’s great. I found this site not even 10 minutes ago and I already LOVE IT. thanks sooo much for your advice. Keep up the good work! :)

    • Cali Bradshaw July 31, 2011 at 6:25 pm #

      Aw thanks hun. Glad you like it. Comments like these are what make me want to keep blogging!

  8. BPJ August 3, 2011 at 1:43 am #

    thanks for sharing this post. I hooked up with my best female friend of 10 years (we lived together 2 years) 9 days ago while camping and she didn’t respond to my text the day after we came home (day after it happened) and didn’t answer or return my call last night. She’s been there for me through some very difficult times and she’d be the one I’d talk to about this if she wasn’t the subject. It’s tearing me apart to think about losing my best friend over this. It sucks.

    We were playing around and then she suddenly “attacked” me and we started making out. It was hot and before I knew it she was on the gravel, laying naked in front of me. While I was eating her out I came up and said, “you know I love, right?” She said, “yeah.” I said I always have and I think we’d do really well as a married couple. And she said, “yeah, we would.” She told me to have “F*** her” and I said, “we can’t do that.” Before going to sleep (in different tents), I asked her if I took advantage of her and she said, “no.” I asked if she took advantage of me and she said, “yes.”

    I have a child and a fiancé (in another country) and I’m moving out-of-state in 9 days. She very much knew that. I’ve now realized how much I really do love my best friend and I want to be with her (I was over that idea). I sometimes think I’d be willing to break up with my fiance and not live with my child (a VERY difficult thing to me). However, I JUST WANT TO TALK TO HER AND SHE IGNORES ME. I don’t want to come on too strong, but I really want to see her before I leave. I feel like I may have lost my “bestie” and, perhaps, my fiance from my guilt. I want to know what she’s thinking … any thoughts on what she could be thinking????

  9. FTJ December 9, 2011 at 7:21 pm #

    Hi, I have read many things on this and I am very confused about the situation I am in. I will explain and Id love to hear responses who have knowledge on this subject or have maybe gone through what I am going through.

    We first met 5 years ago, we worked in the same company and we got along very well. I had a crush on her at the time but she had a boyfriend. Her and her boyfriend broke up a few months into it and I was there supporting her as a friend. We started hanging out during the time her and her boyfriend were broken up. After a few weeks she got back together with her boyfriend and we didnt really talk or communicate. I had moved to a different city and started a relationship as well. After 2 years I moved back to the same city and we became friends for a brief time until my ex called and weirded her out like crazy. We didnt talk again for a few months until we started working together. We slowly regained our friendship that we had years earlier but once again she was in a relationship. I then found myself getting into another relationship and moving away again for work. We lost contact again for a few months, until one day I called her up and had a few hour conversation and since then for the last 6-7 months weve texted every day for all waking hours. I was there through some very tough times lately, like loosing a bf and dropping everything to go back to college. It was huge for her. So when I moved back we went out with friends and we ended up hooking up, where at the end of it I told her I liked her, im not expecting anything but if something happens something happens. I didnt think anything of the sex or anything I just wanted to let her know I liked her. We hung out a few days later where she made a move and kissed me and started rubbing my shoulders and she told me she liked me and I shouldnt like her because of all the drama shes going through. Later that night she informed me that if we wanted to like each other it was going to have to wait until she deals with her shit she has going on and would like to remain friends. I agreed and supported her in everything and remained friends. We recently went on a trip together as friends where some things happened but we didnt hook up. We talked about what was said and she apologized for saying what she said and feels bad for misleading me but she doesnt want to ruin the friendship we have as I mean so much to her and wouldnt want to loose something because we acted on our feelings. We have since talked about it a little bit but it is sort of awkward. What is hard for me right now is she is casually dating. Which is perfect she is only a month or 2 out of a relationship and she needs this sort of thing and I have to be a supportive friend. I dont want to loose the friendship but I also want more and I believe she likes me or she wouldnt say it on more then one occasion. I would talk to her about this as the person above said but its about her and Im sure it would make things awkward lol.

  10. FTJ December 9, 2011 at 7:24 pm #

    oh ya and she recently compared what is happening to when harry met sally

  11. Shaq.P January 4, 2012 at 5:24 am #

    I don’t feel alone about people liking there best friend any more. I met my best friend in high school. I have been liking her ever since the first day of it. But threw my years of high school I notice that my feelings got deeper and I wanted her so bad. I told her how I felt around the 10th grade and I got. I could only see us as friends thing and I was heart broken. I didn’t know what to think when she told me that and I was feeling down for like a week or so. I thought the reason was that she is 2 years older than me and I couldn’t handle her at all. But as I graduate we talked more and more. Now its been 4 and a half years I feel like she is the one for me. I have never been to her house out of the years we’ve known each other due to distance nor have we kissed. Until I came home for college this Christmas break. I have been over her house twice and her family likes me already and we finally kissed. (I made the move) she liked it also but I still think she still wants to be best friends. I’m leaving in 2 days what should I do.

    I have been there for her when she needs me and will continue to do so. I have read so many things and I believe I should continue what I’m doing but wait for her to give me that final thought/ decision On how she feels. What do u think?

  12. Bec January 4, 2012 at 8:52 pm #

    I’ve never hooked up with a friend…they’re friends. You could avoid these problems if you only messed around with people you were dating.
    You can be friends with someone of the opposite sex if you’re mature enough; most of my friends are male and I have absolutely no inclination towards any of them. My ex was an immature ass and cheated on me with two of his female friends; I have never cheated and I can’t imagine doing anything with someone I’m not in a relationship with.
    Perhaps define what you want before you do anything? It seems that the spontaneity of these things is what the real issue is, and not being upfront.

  13. Sam January 6, 2012 at 3:16 am #

    Got a question for you. I was dating this girl for like a year an a half. We recently broke up because I couldn’t handle a friendship she had with this other guy (let’s call him “guy x”). Guy x was her best friend throughout high school and in college (we’re both seniors in college now). They had sex on and off for like 6 months, before he left for Europe and me and her met each other and started dating. At the beginning, I noticed they were always talking, kinda flirting. Like everyday. I told her I wasn’t comfortable with it and she told me I had nothing to worry about and it was nothing. Long story short, guy x found out I didn’t like them talking, so he told her (jokingly apparently) they should have a codeword whenever I was around. She (apparently jokingly) said, yeah we can say hola if he’s here and not hola if he’s not.” WHAT. So, fastforward six months, I’m still dating her, and guy x and her talk like a couple times every month. I never trusted her after that. Was it right for me to ask her to stop talking to him? Or for her to talk to him all the time. NEED GIRLS ADVICE!

  14. Ya don't know me, hun. February 27, 2012 at 7:42 am #

    It’s upsetting when you loose a friend over a “bestie hookup”. I never have, but a lot of my friends have. Me and my female best friend (I’m female too) have been “experimenting” with each other lately, but I don’t think we’ll hook up.

  15. Dani December 24, 2012 at 10:05 pm #

    Hi I just found this and I need help badly. My ex and I dated when we were 14 for about 3 months. He dumped me cause he said I was too clingy. And I was lol. We’re 20 now. He’s moving back home from Colorado and has nowhere to go. His family kicked him out. He has no job. He’s coming home tomorrow. My family is letting him stay with us. But I still have feelings for him. And when we talk sometimes he gets flirty, and every guy I tell him I like he calls them a fag lol which I heard is jealousy. So what should I do? I’d like to hook up with him but I dunno. We’ve been best friends since we were 13. So do you think there’s a chance we might get back together? He still uses “we”. He’ll be like what game should we play? Or I’m trying to find a movie we can watch. So what do you think? Lol

  16. Band*Geek December 26, 2012 at 1:03 am #

    I’m seventeen and I recently hooked up with my best friend (we’ve been best friends since we were five). Needless to say your site helped settle a lot of the things that were spinning in my brain!!!! At different points along the years we’ve had feelings for eachother but we’ve just never been on the same page. Right now I’m not expecting things to change because of how we both are but reading this blog helped immensely. Thank you Cali <3

  17. K April 14, 2013 at 10:03 pm #

    My best friend and I have just recently started hooking up after being friends for 10 years. As long as you can talk about exactly what is expected from each other, it CAN work. There is no awkwardness, no strings attached, and it is probably the most fun either of us have had when it comes to sex. Just be open with each other about what you want and it will work out just fine :)

  18. palmspringsgirl September 6, 2013 at 6:55 am #

    I wish I read this before I hooked up with my best friend… it would of saved me a lot of heartbreak.
    1) Being close to him I knew he was in no state to be in a relationship, for one he has a lot of growing up to do (as do I) and doesn’t want to be responsible for anyones feelings except his own and two he is still in love with his ex.
    2) He is also going through some sort of weird phase where he doesn’t know what he wants to do with his life.
    3) He already recently had a friend/fuck buddy which bugged the crap out of me. Even though our relationship was closer than theirs was of course I couldn’t help but compare myself to her.
    4) Went into it on completely separate pages, I wanted to date he wanted it to be casual. I was kidding myself when I thought I could be casual. But I don’t know bc we were close he would always tell me things like “i wish i had a girlfriend” blah blah blah. Basically like you said, I thought I could be different, boy was I wrong.
    5) Found out he always saw me as just a friend the before during and after. So that’s cool. So basically you used me to fill a void of loneliness, being horny and emotional unavailability. Couldn’t you have done that with someone you weren’t best friends with?!

    Equally responsible since I put myself in this situation. But man, shit hurts.

  19. Vivian September 19, 2013 at 11:59 pm #

    I wish I read this before-my life is a mess right now -I’ve violated most of the points and probably will loose him for good- I don’t even know what I want from myself and not to mention from him-how the time passes I am not at peace with all that happened-I called him on a date to talk about it and I have no absolute idea what to say-HELP please:(
    Here is the problem:
    Crossed the line completely while he was drunk , I was sober(I have no idea why I did it) we’ve been friends for 3years we had unpleasant history in high school (I had crash on him and it turned out a mess -we didn’ t speak to each other for 7 years and got back friends again more like siblings) and now this happened.
    I couldn’t have done more stupid thing -I admit!

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