Taking A Run At An Old Flame

Taking A Run At An Old Flame

With the exception of a spectacularly slutty phase during sophomore year, I spent most of college as a relationship girl. I went to college having a boyfriend from home… until that ended and I went full-on nympho sophomore year. Then in my junior year, I had two boyfriends: the one I actually loved and then the one I settled for after the first one broke my heart. They were followed by a succession of short-term boyfriends senior year, but let’s be honest – I was too busy drinking away my abject horror at the imminent entrance into the real world for any of them to take hold and become something more serious.

Now let’s focus on the one who broke my heart, because he is the subject of this little story. He married the next girl he dated – something that has happened to me a grand total of four times, which I believe makes me a starter wife without the perks of the ring or the wedding. Anyway, despite a not entirely amicable breakup, we managed to maintain a level of civility since our respective best friends married each other and we were forced to be in each other’s presence on numerous occasions. Then, as those friendships faded (on my side, anyway), we saw each other less and less until he became a rose-colored memory in my rearview mirror.

Until last week, that is. We had maintained a social-media-only friendship because I don’t listen to my own advice and a picture he posted popped up on my timeline that would imply that he was no longer living in the state of matrimony. A bit of internet creeping confirmed that he was indeed back on the market, and a nagging thought started to take hold at the back of my mind…should I slide into his DMs? I’m single at the moment, with no current prospects on the horizon, and it’s always nice to have someone to talk with… even if it doesn’t amount to anything. What’s the worst that could happen, right?

Except that I didn’t know what to say. I have literally zero experience at such things and I’m not exactly known for my subtlety. So I went to the place I usually go to ask the important questions in life: Twitter. I asked my sweet 2000+ following (all of whom I am sure are humans and not porn bots) how to approach the situation without coming off as a total weirdo. Along with the usual responses (boobs for the win!) came a question I wasn’t quite prepared for:

Well, Craig-fucking-Sanderson, thanks for bursting my “we are going to have a romantic story to tell our grandkids” bubble. But once I stopped calling Craig an ass for ruining the possible new relationship I had dreamed up in my head, I started to ponder that last sentence: “If it didn’t work before, it won’t work now.” I wondered if dear Craig was indeed right. Does a long ago romantic failure mean that the same two people can’t have a successful relationship later on? Or, is it possible that once you are older and wiser and circumstances are different, that those same two people could work out this time? Of course, romance novels and romantic comedies would tell us the latter is true, and my ever-hopeful heart is inclined to believe it. But in reality, is the relationship re-do simply an urban legend of which there are few, if any, success stories?

Well, to be frank, I’m not sure. But I can tell you this: I slid like a third base runner stealing home into his DMs, and we’ve been talking every day since. So I guess I’ll let you know how it turns out, Craig.

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Jenna Crowley

Jenna used to be known as 2NOTBrokeGirls, but then one of the girls actually went broke, so she's struck out on her own. Jenna spends her free time saving the world, one sorority girl at a time (usually while wearing yoga pants), questioning why she decided to get a doctorate, documenting her love of all things cheese related, and hosting the new PGP podcast Don't Take It From Us. You can ask her anything you want about football, using your boobs to get what you want, and pizza at @JennaLCrowley on Twitter or via email at

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