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Most. Awkward. Night. Ever.

12 Mar

It is possible there have been other awkward nights in the history of the world, but I am fairly certain that none have been THIS awkward. Please, allow me to elaborate and then you tell me if this wins the most awkward night ever award.

The awkwardness begins:

So this afternoon I get a text from Mr. Cute but Whiny’s friend asking me what I was up to for the evening. I find this strange because after he kissed me and asked me to lunch, I never heard from him again. I’ve been assuming that Mr. Cute but Whiny made him feel bad for hanging out with me because the friend stopped calling me right as the ex began trying to weasel his way back in. Anyway, we text back and forth and he informs me that he and my ex are going to the same bar my friends and I always go to. We figure, whatever, let’s still go.

Awkward at Johnny V’s:

So we arrive at the bar and Mr. Cute but Whiny goes, “Oh you must be here because you saw my foursquare check in!” Uh no. Self-centered much? I tell him I am here because his friend texted me and invited me. Awkward, but at least it shut him up for a minute.

Anywho, I am trying to talk to/flirt with the friend (but just for fun, as I am still a little peeved that he went so MIA) and as I am teasing him about the last time we hung out the ex goes, “Oh you mean the time you guys made out? Yea, he told me.” Um what! Awkward. Way to kiss and tell, friend. And way to call me out on it, ex. I turn bright red and quickly excuse myself.

Awkward and Senti:

Upon my return, the ex corners me and wants to talk about our friendship. Awkward. By this point, my friends have left me, and rightly so, as this is just too much drama. The conversation goes like this. Him: But I really want to be friends. Me: But I don’t. And back and forth for like 30 mins until I get interrupted by a text from another friend. She informs me that Mr. Not Quite Right is at a bar with her just a few feet away and that he looks like shit and that I should come meet them. My heart stops. This is the same Mr. Not Quite Right that I haven’t seen in almost a year. The one who I have zero contact with since he blocked me on FB. The one I have been dying to see and unsure of whether i would punch him or hug him. So I tell Mr. Cute but Whiny,” Ok, you want to be my friend? Then come to Bubs with me.” I explain the situation (he knows all about Mr. Not Quite Right) and so he says yes, we’ll go. Awkward, but useful.

Awkward at Bubs:

So Mr. Cute but Whiny (aka Mr. CBW) agrees to play arm candy and we go up to the group where The Ex is. Mr. Not Quite Right doesn’t say anything at first as all of his friends are giving me hugs, and saying hi to Mr, CBW, whom most of them have met. The Ex is just staring at him (I am sure thinking who the eff is this guy??).

Side bar: I don’t think it is possible for two guys to look more different than these two. Picture this – Mr. CBW is preppy as per usj: wearing an argyle sweater and a pea coat and has super dark hair, and scruff. The Ex is much more casual – blonde, wearing flannel, jeans and a hat. AND he really needs a hair cut.

But I digress. So I say hi to The Ex and do the obligatory hug, and then introduce Mr. CBW. For as much as I hate him sometimes, homeboy played the part so well. He acted super cool, nice and friendly. Mission accomplished, Mr. CBW and I exit to go get a drink.

Awkward with The Ex:

10 seconds later I decide to go back and talk to The Ex. I mean, hey, it has been a year and I have a lot to say. He is totally putting up walls at first but I break them down with my teasing and by telling him I fell on my butt during my kickball game that night. That he enjoys. After a bit of talking he asks if we can be friends (I’ve heard this before, sir) and so I respond, SURE if you un-block me on Facebook. We start to go down the whole, “well you did this and I did this awkward road,” but then I stop it. I realize, honestly, I just want to talk to him. So we end up talking for a little over an hour, just about everything. It was so wonderful and not at all awkward. Until…

Awkward with The Exs Friend:

Until, The Ex’s best friend comes up, interrupts us and goes, “You know I asked Cali out right? Like on a date?” (This is true and I turned him down). Of course, this gets The Ex riled up and he’s all upset at his bestie, “Why would you do that? You know we dated. That’s so not cool…” yada yada yada. I try and diffuse the situation but Mr. Not Quite Right has always been a jealous guy and it was getting awkward, fast. Then his bestie starts talking about how much he hates The Ex’s current girlfriend (so awkward for me but not a surprise. Every single one of his friends has told me how much they love and miss me) and I can see Mr. NQR just trying to keep his cool. His bestie keeps flaming the fire and at one point asks me to go home with him. Note, I have zero desire to do so, but apparently no one cares about what I want, and so then it turns into this whole big fight between them. Eventually they get so heated they leave and I take my super awkward self home.

So, what are my takeaways from this evening, you ask?

A. Hanging out with two exs in one night is hard. Especially if they are in the same place. Butttt also a little fun if one will play along.

B. Stay away from your ex’s friends. They cause drama and awkwardness. You + Ex’s friend = Bad things.

Lesson learned. So what do you think? Awkward night or what?

10 Responses to “Most. Awkward. Night. Ever.”

  1. Single Steve March 14, 2011 at 3:53 am #

    Oh Ms. Bradshaw….I hate to say I told you so…but I dating your ex friends is always a bad idea. My friend is dating my ex and it’s super awkward for me and her and him and everyone. And we broke up over 2 years ago.

    According to a recent census there are 217,032 people between the ages of 25 and 34 that live in San Diego. I’m willing to bet a few of them don’t know your ex-es. Good luck!

    • Cali Bradshaw March 14, 2011 at 3:55 am #

      Bwhahaha love that stat. I am telling my roomie right now that hope is not lost for us!

  2. Susan Walsh March 14, 2011 at 12:34 pm #

    Oh boy, I’m getting totally hooked. Now I have to go back into your archives and find out what’s up with all these characters. You have a real knack for storytelling, Cali!

    • Cali Bradshaw March 14, 2011 at 3:52 pm #

      Haha, thank you Susan! I swear, writing it all down makes life a million times easier. Glad you enjoyed it!

  3. yohami March 16, 2011 at 7:25 pm #

    aw fuck. so much drama. such a drama appetite. you complain about the dating world in the facebook era, but it looks like it was done solely for you.

    enjoy. burp.

    • Cali Bradshaw March 17, 2011 at 1:42 am #

      Not sure I am complaining. Just making observations.

  4. yohami March 16, 2011 at 7:28 pm #

    they are not “in the same place”, you orchestated it, its not like it just happened, so kudos for the creativity

    now that you are at it, go with plan B, but actually go a notch further and sleep with both guys and get pregnant, then we can start a sitcom “two and a half dads”, who needs charly sheen?

    • Cali Bradshaw March 17, 2011 at 1:42 am #

      Whoaaa hostile much? Deep breath, dude. It was just a story…

      • yohami March 17, 2011 at 4:32 am #

        yeah, sorry for the hostility. Im fed up on girls drama recently

        • Cali Bradshaw March 17, 2011 at 4:39 am #

          Well on behalf of woman everywhere, I wish you a drama free future!

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