pressure much?

28 Jul

AHH! Get me out of here!!

I think I may have just gotten myself into an awkward situation (when DON’T I get myself into awkward situations?)…

So, tonight my 30-something bachelor (playbook page to come soon) is having an impromptu house-warming party on his amazing terrace. Being it’s a Thursday night and I’m off tomorrow,  naturally I plan on making a night out of it. Wanting others to experience the amazing terrace with me,  naturally I’m planning on inviting others to make a night of it, as well.

Among this list of select few, who get to eat drink and be merry on one of the most amazing terraces I’ve ever seen, is my old boss. She is a 30-something bachelorette whose desired stats probably match quite well with my 30-something bachelor. I am NOT planning on giving away my bachelor, but I’m pretty sure where there will be one, there will be many. So although it will be fun to see her outside of work in general, I hope she might meet someone who could take her on a date. She works hard and deserves it.

BUT… here comes the possible awkward, right? Awkward scenario #1: There is a Carrie Bradshaw/Candice Bergen moment where at some point during the evening, in a drunken admission, she asks me why I’m stealing men that are in her dating range. Awkward scenario #2: She comes and doesn’t meet anyone she likes. OR even worse… she comes, meets someone she likes but he doesn’t like her. UGH. Cringing at the thought already. Awkward scenario #3: She meets someone, they date for a while, they break-up and then I’m stuck in the awkward Who’s side are you on anyway? convos.

Ok. Probably over thinking this… I’m sure it will all be fine. It doesn’t help that the last time I tried to “hook” people up, it worked too well and now my best friend has been dating my ex-coworker for over a year; I never hear from either one of them anymore. Ugh. Now I’m even more nervous.

So, I may not have advice to offer on this one yet, but I’ll keep you posted.

(Possibly) Awkward night on the terrace… here I come!


2 Responses to “pressure much?”

  1. sarra65 July 28, 2011 at 7:06 pm #

    LOVE this! I know how you feel. I’m a 21 year old student-come-tv junior researcher dating a 37 year old, married (but his wife says it’s fine….apparently) man with the body of a god. I have bridget jones moments every day.

    • LittleRed Writing Hood July 30, 2011 at 4:40 am #

      Hahaha @Sarra65 My boss who came with me literally said, “You need to ditch your other guys for {thirty-something bachelor}.” Unfortunately, as you are aware, it’s never that simple! She didn’t find a love connection, but she had a really great time. Thanks for reading! xo Red.

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