Auntie SparkNotes: Should I Catch Up With My Old Crush?

Dear Auntie,

This guy, let’s call him, A, has been in my life since before either of us were born. His parents went to high school with my parents, and our moms are still very good friends. He and I were never really very close until I started struggling in math in high school, and his mom gave him my number so he could help me. My junior year of high school (four years ago) I had a crazy huge crush on him. This crush continued until last fall.

Problem was, he had a girlfriend. But he would text me mildly flirty texts (never anything sexual), which confused me and made me feel awkward and guilty whenever I was around his girlfriend. We weren’t super close, but friendly and talked quite a bit. He even gave me a ride home one evening when our shifts ended around the same time.

I managed to give up my crush on him last summer, and even had him and his girlfriend and her best friend over to my house for my associates degree graduation party, and we all got along great. He proposed to his girlfriend and was engaged last fall. Eventually, we quit talking, because we just didn’t have much in common (and his fiancée still wasn’t fond of me).

This summer, however, they broke up. He had another girlfriend within a month or two, and they dated until a couple weeks ago. Then yesterday, he messaged me on an online dating service we’re both on, to say hi. Then today we started texting, and several times when I asked about various events in his life, he said they were “too complicated for text”. He wants to catch up in person.

So, basically Auntie, I’m nervous and afraid of getting my heart broken. Am I reading too much into this? Would I be stupid and terrible to engage in any non-platonic relationship with him? (I should point out, if it were to come to anything, it would be my first relationship). I did point out that I was not after a hookup (and the site he messaged me on was not Tinder), and he said he was after a real relationship. Should I just not meet him at all to catch up?

Well, I’ll give you this, Sparkler: Not meeting up with the guy at all would certainly reduce the chances of getting your heart broken.

The problem is, it also brings the chances of everything else down to nil, too, including a lot of positive, fun, or even just neutral outcomes. Might this be the meeting that finally brings you together romantically? Maybe! But even if you guys didn’t wind up falling into a whirlwind love affair, moving to Fiji, and spending the rest of your lives adopting rescue pugs and having passionate sexual intercourse, there’s a whole world of possibilities here that don’t involve anguish and heartbreak, but do involve you moving forward with more and better information than you currently have. You could discover that the vibe between you has become more platonic than romantic, all on its own, since you last hung out. You might realize after an hour of chit-chat that you just don’t have anything in common anymore. Maybe he’ll be forty pounds heavier, covered in warts, and wearing a velour sweatsuit with a stain on the crotch, and the conversation will be so excruciatingly boring that you fake your own death to escape it.

Literally anything could happen, Sparkler!

Unless you don’t go, of course, in which case nothing will.

But that’s the thing, and I suspect that it’s the thing that’s really bothering you. I mean, let’s be real: The chances of this guy managing to break your heart over the course of a single meetup are somewhere between minuscule and nonexistent. What you’re really afraid of is not the likely outcome of catching up with him, but of the fact that there are lots of likely outcomes, with no way of telling which one you might get. That’s why you’re analyzing the situation to death in search of some certainty, and why you’re trying to hedge your bets against heartbreak by asking him about his intentions—even though you surely realize that he can’t see what the future holds anymore than you can. That’s the nature of relationships: you don’t get any guarantees. Opening yourself up to the possibility of falling in love always means opening yourself up to the possibility of pain down the road. (Some might even say the inevitability, since even the happiest relationship on earth can only last as long as both parties’ lives do.)

What you need to realize is that it’s okay to take that risk. If not with this guy, then at least as a general rule. And that’s not just because the potential positive outcomes are well worth it, but also because your worst-case scenario is completely survivable. Human beings are resilient; we can handle having our feelings hurt. You just have to go after the things you want, and have faith that you can weather the disappointment if you end up not getting it.

So if you want to see this guy—because you’d like to explore the possibility of dating him, or just because it would be fun to get out of the house and catch up with an old friend for an afternoon—then do it. (Not to mention that if you do go, he’ll probably spill all the juicy, dirty details of his broken engagement, and you know you want to hear about that train wreck… or at least, I sure would!) Don’t be afraid of a little uncertainty. It’s okay to make a choice and see what happens. Because whatever happens, I promise, it won’t be anything you can’t handle.

Got something to say? Tell us in the comments! And to get advice from Auntie, email her at advice@sparknotes.com.
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