Ask Dr. Nerdlove by Harris O'Malley

Can I Have a Second Chance With My High-School Crush?

DEAR DR. NERDLOVE: I could use a bit of advice. There is this girl that I had a crush on in high-school, and I am pretty sure she reciprocated it. I didn’t do anything at the time for a variety of reasons, chiefly I was being a coward. I take a bit of solace in that I would have been a crappy boyfriend at the time, and have since become a better man and better in relationships. Anyway, not doing anything is my biggest regret to date that anything can be done about. She lives a couple hours away from me now, and as far as I can tell she is single. I don’t have her number or email address anymore, but I can message her on Facebook.

I would like your advice on whether or not I should reach out to try and reconnect. I don’t want to come off as a creeper. I was thinking of reaching out to reconnect and invite her to coffee the next time she is in town (she still has family where I am). I figure I shouldn’t lay it all on the line saying that I regret not asking her out 8ish years ago. That seems kind of creepy.

Regardless of what I say, even if it doesn’t go my way, it won’t be that bad. The absolute worst that could happen is she thinks I am a huge creeper and says so to all of our old mutual friends and they have a laugh. I’ve lost touch with most of them, so no skin off my back. The best that could happen is we have coffee or whatever and things go well and they lead to a relationship.

So, I guess what I am asking is should I reach out or am I being an idiot? If I should reach out, should I avoid laying it all on the line? I could use some brutal honesty here. That is why I like you advice articles, you don’t pussy-foot around.

Second Time Around

DEAR SECOND TIME AROUND: So I have a question, STA: it’s been eight years… why are you still hung up on this woman? Eight years is a long goddamn time to hold on to a high-school crush, especially when you’ve been completely out of touch.

Don’t get me wrong, I can totally understand the feelings of frustration when you’re dealing with someone you see as The One Who Got Away but at this point, do you really even know who she is any more? You’re not the same person you were back in high-school… so why do you think she’s the same person you had a crush on? I think it might do you some good to ask yourself whether you’re still into her for herself or because of what she represents. Chasing after someone who’s more symbol than person – your unicorn, your white whale, whatever – isn’t fair to her and it’s incredibly disrespectful; she’s a person, not a fantasy, y’know? And it’s not good for your personal development to hang on to all of those missed opportunities; when you’re stuck looking back at all of those might-have-beens and woulda-coulda-shoulda moments, you end up missing out on the opportunities that you do have.

Now, does this mean that you shouldn’t send her a friend request on Facebook and see if she’s interested in reconnecting? Not necessarily. Facebook has basically become the replacement for the high-school reunion and it’s not weird to want to reconnect with people you knew. But I think you need to be careful and you need to be realistic. The odds are that you probably aren’t going to get together and in your current state of mind, it’d be a mistake to try. Some regrets are better left as regrets and allowed to fade with time. You want brutal honesty, I’m going to be brutally honest: I don’t think this is the greatest idea. But I also think you’re less asking me for advice and more for permission for something you want to do anyway. So with that in mind:

If you’re going to reconnect with her, don’t do it with the intentions of trying to correct your mistake from all those years ago. Treat this as simply trying to connect with someone new. Get to know who she is now, rather than who she used to be. Learn to see her a a person instead of the fantasy you’ve had rolling around in your head for the past eight years. Get coffee if she’s amenable to it. Do not lay out that you’ve been dying to ask her out since high-school; you’re right, dumping all of that on her would be incredibly f

king creepy. Simply play catch up. No dates. No hooking up. No even hinting at it. No being Mr. Nice Guy and trying to backdoor your way into a relationship with her.

If – and I’m going to need you to be brutally honest with yourself – you’re able to let go of that fantasy and connect with her as a person – then you can bring up that you had a crush on her. “You know, it’s crazy and I can’t believe I’m saying this but when we were in high-school, I had the hugest crush on you and I have to admit, I’m kind of disappointed that I never managed to ask you out.” And then leave it at that; something crazy that happened in high-school. But you’re not in high-school any more and neither is she. Let the fantasy go and maybe, just maybe, you might find a genuine friendship with the person underneath.

Good luck.

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