On the one that got away

I met a girl when I was in law school (she was a “townie”) and had a fun but short relationship with her.  I broke up with her because I was stressed and overwhelmed with law school and there were some law school hootchies sniffing around.  She’s an awesome girl but I admit that I didn’t think she was a long-term prospect at the time.  I think I really hurt her because she wanted it to turn into something serious.  I almost immediately regretted the decision to break up with her. Since then we’ve been “friends”. We live in different cities but we text and hang out when I’m in Chicago.  I think she’s over it all but I want to tell her how bad I screwed up by killing the relationship.  My instinct is to just tell her.  But my instinct was to break up with her, too.  Christ, was there a question in there?

Nope, and you spelled hoochies wrong. That’s probably a word you should learn now that you’re a lawyer.

Listen, you thought pretty highly of yourself back in the Chicago days. That’s all well and good, but if you’re being honest you’ll admit that this chick wasn’t really up to your superficial standards at the time. She was a good woman, but you had some douchebaggery to get out of your system, so ultimately the timing was off. Fine. Whatever. Shit happens and life goes on.

Cut to today. A few extra pounds, a little less hair, and that suit you wear to work is starting to itch a little. Every morning when you pull tight that half windsor knot, it makes a sound like your mother asking when you’re finally gonna meet a nice girl and settle down.

So you wonder. Did you fuck it up with the townie in law school? Was she the one and you missed it? It plagues you a little bit, because when you fantasize about the wife and kids that will eventually cry at your funeral, it’s her face that you see filled with tears.

That’s what you’re trying to ask me here, dude. You want to know if she was the one. Thing is, that shit sounds ridiculous when you say it out loud, so you can’t quite bring yourself to ask a stranger on the internet to magic eight-ball your girl that got away.

Well, she wasn’t the one.

Quit romanticizing old relationships. You’re too young for that kind of sentimental nonsense. Feel free to tell her that you screwed up, but don’t expect her to go all Lifetime mini-series weepy on you. She might appreciate it. She might not care. Either way, the past is still the past, and she ain’t your future wife.


Leave a Reply

Your email address will not be published. Required fields are marked *