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Auntie SparkNotes: Can I Ask My Flirty Friend to Set Me Up?

Hi Auntie!

Apologies if the following sounds like the plot of a super cheesy teen drama show, but that’s my life, apparently!

So two whole years ago, I had a huge crush on a friend of mine, who we’ll call Sebastian. After some intense flirting, I put on my confidence pants and told him how I felt, and he proceeded to lead me along for months while he chose between my then-best friend (with whom I’m no longer friends, for completely unrelated reasons) and me. Eventually, I took my self-esteem out of the closet and removed myself from the situation (because I deserve better), and the two of them got together.

This past summer, they broke up (because he “doesn’t want to be tied down senior year,” his words), and, because I have absolutely zero self preservation, he and I became friends again. I think some part of me is always going to have a thing for him, and the chemistry is still there, but my rational mind is still in control, so I won’t act on it. In fact, I even have a crush on a totally different guy!

Except, as soon as Sebastian found out about my crush, he stopped flirting with all other girls (he’s something of a player) and starting focusing 100% of his energy on me, bringing me flowers and carrying my books to class and complimenting me nonstop and putting his arm around me and so on and so forth. I know that if I were to reciprocate, he’d immediately pull away, but the attention is still nice for my ego (as bad as that is) and so I stick around. Also, I’m 60% sure he doesn’t have feelings full stop.

My biggest question is: do I need to put a stop to this relationship? I know it isn’t going anywhere, he knows it isn’t going anywhere, and I really do enjoy his company, even without the whole flirting thing. I forgot how much I liked him as a friend, and I don’t really want to lose him again. Also, while my rational side will not let this progress, my poor, teenage hormones are really loving this chemistry and all of the flirting.

One more thing: usually, Sebastian sets up his friends with guys he’s friends with if they have crushes on said guys without the friend even having to ask. He knows I have feelings for this new guy, he is friends with him, and yet he hasn’t tried to set me up at all. Would I be a bad person if I just asked him to do so, even though Sebastian himself is flirting with me?

A bad person? Oh, honey. No. Actually, if I’m being really honest, I would suggest that Sebastian being asked to set you up with one of his guy friends would be the best kind of poetic justice, and precisely the epic punch to the ego that your old pal deserves. (I would also suggest that you take a time-lapse picture of his face at the moment you make your request, so that you can capture the entire schadenfreudelicious experience in exquisite HD.)

Because as you so evidently already know, your friend is kind of an asshat — albeit an asshat whose company you genuinely enjoy and with whom you have fantastic chemistry. But that mutual fondness nonwithstanding, between the way he toyed with your emotions back in the day, and the way he then dropped everything to do it again upon realizing that you had feelings for someone else, it’s pretty obvious that Sebastian sees you as a sort of trophy flirtation and gets his jollies by keeping you on the hook and away from other dudes. (That is, unless he’s had a genuine change of heart — but you know him better than I do, so I’m just gonna trust that you’re correct about his character and motivations.)

In short, if you did want to ask for his help in getting the guy you like, he’s certainly forfeited his right to be wounded.

However, it also occurs to me that he might not see it that way. And more to the point, I wonder if you really want to give this apparently incredibly selfish person any kind of control over your romantic happiness, when what you want goes against his interest in keeping you to himself. Aren’t you worried that he’ll try to sabotage you? I would be, if I were you!

…That is, unless my real goal was not to get set up with my crush, but to give my asshat friend a nice, fat kick in the feelings.

Which brings us back to the original point: You’re under no obligation to be considerate of Sebastian, given the way he’s treated you. You can do whatever you want on that count, whether it’s continuing to enjoy him as a source of meaningless flirty fun, or asking him to set you up with his friend — and you can even do the latter for no other reason than that you want to give him a taste of his own medicine (petty, sure, but hardly undeserved).

But if, by any chance, you’re hoping that this will spur Sebastian to be overcome with regret, to realize that he wants only you, and to fall immediately into your arms forever and ever and ever — or in other words, if all your claims of being uninterested in a relationship with him were kind of a bunch of baloney— then you need to be honest with yourself about that, as well as about the (virtually nonexistent) likelihood of actually having that happen. So think about it, be real about what you’re hoping to accomplish, and then make your choices accordingly. And whatever that choice might be, do write back to let us know what happened… and feel free not to skimp on the sordid details, hee hee.

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