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Wednesday, March 1, 2017

Is It Weird to Date the Roommate of Someone You Dated Before?

Dear Bro Jo,

I'm a 20-year-old young lass with very little dating experience. Despite being a beautiful, hilarious, incredibly intelligent (humble), gem of a person, I've only ever been on two first dates. Yes, two. I'm 20. Two first dates. It's fine.

The first time I got asked on a date, I was 19. I was uber excited to get to know this handsome young gentleman, we hit it off immediately, and were absolutely inseparable for about two months, before he received his mission call. We decided to cool our jets at that point.

Long story short, he ended up not going on said mission, and we were kind of back-and-forth between friendship/more-than-friendship (whiplash) throughout this past summer. Basically, my whole relationship with this fellow was a huge mess for many reasons.

Here's the predicament. For the first three months of knowing this boy, he had roommates that I spent a lot of time with and considered friends. There was one, in particular, who always impressed me with his humor, character, and smarts.


He's the former roommate of someone I dated, and, if we ever dated, he'd go into it being very much aware of the fact that I had kissed one of his friends. Many, much, multiple times. Bad news, bears.

I tell myself over and over again how complicated that could be, but I'm still drawn to this man that I haven't even seen in almost a year. I've been wanting to reach out to him in some way for months but have no idea how to do so.

What in the world is a girl to do?

Risk some potential super-mega-awkwardness or keep waiting (un)patiently for the third first date?

Thank you,

Roommate Lovin'

Dear RL,

Can you explain to me how someone who's as goofy and outgoing as you are in your email sits around for a year waiting for someone else to make something happen in her life???

Sure, this guy may have a hang up that you made-out (often) with his roommate . . . lots of Good Guys would have the same problem.  But it's not like you made out with EVERY guy in the apartment (right?), and a big chunk of time has passed.

Now, sure, I think it's WEIRD, and more than a bit stalker-y, that you're this hung up on a guy that you haven't even seen in a year, and YEAH, I think you should focus on the guys that are Actually In Your Life . . . AND I certainly hope that the reason you know he's still available is because you queried a mutual friend, not that you Facebook Stalked him . . .

If that's true, I think that's your "in".

I think you need a mutual friend to speak up for you.  If you call, text, email, drop by, show up where he works . . . all of that is creepy.  Even if you are (and by the sound of things you just may be) that desperate, you certainly don't want to come across as such.

So have a mutual friend go up and either re-introduce you or talk to him on your behalf.  Have said friend ask if he remembers you, tell him you think he's attractive, that you're single now, and you hope that if he remembers you he'll ask you out.  Said friend could offer to set up a "blind date" if he doesn't remember you.

If you have no mutual friends . . . well . . . then I think the best non-creepy thing you could do is to sent him a simple card.  I get a lot of "that sounds really old fashioned" eye-rolls when I mention sending cards or writing by hand but, believe me, if he has any interest in you it will work.  Just keep it simple.  And be sure to include your phone number.

Good luck!

- Bro Jo

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