Sasha Answers: Go for the work dude

September 17, 2012 19:07:58 Posted at September 17, 2012 19:07:58
Sasha Posted by Sasha

Hey Sasha!  I'm pushing 30, single, and all my friends are married. Even my baby brother. They all go out for group dinners, double dates, weekends up north and all that - couples only. Since they rarely invite me out with them, I really have no idea where to meet guys at this age. I'm not a club scene kind of girl, nor am I into the online dating thing. And let's face it, my friends don't really give a crap about setting me up while they're in their marriage bubble (I'm not bitter, I swear).
Currently there's this guy at work that has potential. We have good conversation, we have some things in common, he makes me laugh. I'm thinking of giving it a whirl, but I'm really worried about things exploding in a very bad way. I do love my job, it's my dream job, so I wouldn't want to ruin or complicate things here. BUT, we work in completely different departments on different floors and don't really ever run into each other. Work dude seems interested. He goes out of his way to come to see me every so often, he's chatty, he's touchy (in a non-creepy way) and he's casually asked me out a few times (once in a small group-ish kind of setting). Each time I was caught way off guard and my awkwardness took over and I said no (ugh). I've said no to him every time and I don't even know if he'll ask me out again. How do I damage control the multiple "no" situation and re-approach this coworker in a sane, slightly casual, could-either-be-friends-or-possible-dating-potential in a normal way? Or is this a horrible idea altogether? Thanks! M.

You just spent the whole first paragraph telling me you don’t want to be single and then the whole second paragraph telling me there is a guy you’re interested in.

Are you on crack or am I?

M, I know the thought of being rejected is a disgusting and gross reality, but lucky for you all signs point to the fact that this guy is interested. Ding! Ding! Ding! So instead of trying to convince yourself that you’re not worth it - by the way, stop doing that - give your self-esteem a break and go for it.

Look, I don’t have any swagger, in fact I have zero, but this one’s easy – organize an after work drink with him and some work buddies, and just see how it goes.  Take some initiative and have some fun.  I’m not promising this guy will be The One, but the only way to get some game is to get back into one.

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