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Auntie SparkNotes: Should I Re-Like My Crush?

Hi Auntie!
I’m a 16-year-old black female in a prep boarding school. I’ve been bullied about having dark skin for years, and it wasn’t until I came to my boarding school that I escaped all of this. However, I’ve never had anyone tell me I’m pretty, so whenever I get any attention from a guy, it’s pretty significant.

The problem: I like this guy who’s being extremely complicated. At first, I thought he liked me. A bunch of us were hanging out one night, and he would always redirect conversations to me, stand up for me if one of my friends was (jokingly) making fun of me, and he randomly came up to me twice asking for a hug—the second time picking me up and spinning me around. When we had to leave, my friend (who happens to like him too) asked him for a hug and he was like “Sorry, not really a hugger,” then literally came over and hugged me that second. I know it’s small, but guys don’t usually treat me like this, so I was stunned.

So we talked on snapchat for like 2 weeks, then all of a sudden he started ignoring me. I would say hey to him, and he would quickly say “Hi, I’m in a rush,” then go talk to some friends. I found out a few days ago that he knew I liked him at that time, but I still just wanted to be friends because I genuinely like him as a person. I was really hurt because what I was bullied for in elementary and middle school seemed true: no one would like me because I’m black and have dark skin, so for my benefit, I stopped talking to him and trying.

Fast forward to a little less than a week ago, he snapchatted me out of the blue saying, “Hey, I haven’t seen you today.” Mind you, he had been just about to start a relationship with a girl I know, but she realized she lost feelings and dumped him. So with this in mind, I simply say back, “Yeah I’ve been busy.” He responds “Oh ok, lol” and I leave him on read.

He then STILL responds about two hours later (though I left him on read) with a funny selfie. Since then, we’ve been snapping back and forth again, and even in public he’ll compliment my lipstick or tell me he loves me (jokingly) or he hates me (jokingly), and this past weekend when my friends were making fun of me again he put his arm around me. He let me rest my head on his shoulder, and rested his on top of mine. My friends kept making faces at me the whole time, and every time he left for a split second they would tell me he was flirting and how to flirt back. When he came back, I tried to convince him to come to the homecoming dance, but he said he’d rather be antisocial. He playfully let me pull him a little while towards the dance, then pulled away and said he really doesn’t do dances and left. He snapchatted me later saying “You only wanted me to stay so that you could dance with me.” I responded, “Wow you got a lot of confidence, don’t you?” and he said “Haha I’m joking, or am I,” then I said, “What are you implying?” and he goes “Dude I’m just joking, or am I” and it just kept going. I never admitted that I wanted to dance with him though.

We’re friends again, but I don’t know if I should like him again. I don’t know if he’s only being flirty, and not showing actual signs of interest or wanting to progress anything, or if he’s just being weird about it. I just want to be careful and not get myself hurt. What do you think?

Wellllll… for starters, I think you need to dial down your expectations to something at least resembling reality.

Because if your primary objective here is to be careful—so careful that you never embark on any romantic pursuit which might result in you getting your feelings hurt—then your only option from this day on is to hide in a hermetically-sealed bubble and never seek the company of another human being, ever. Anything else is just too risky!

And, uh, also? It’s too late.

You ask if you should like this guy again as though you had a choice in the matter, but let’s be honest, that ship has sailed. You, my friend, have caught a raging case of Feelings for this dude. (If you hadn’t, you wouldn’t be hyper-analyzing every single solitary interaction you’ve ever had and driving yourself nuts wondering what it all means.) Instead, what you’re really looking for is a guaranteed way of knowing that he likes you, so that you can pursue him without fear of embarrassment or rejection.

The bad news, darling, is that there is no such thing. When you open yourself to the possibility of romance, you also open yourself to the risk of heartbreak. Even now, if you found out that this guy was just messing around and didn’t have any real feelings for you, it’s not like you’d simply shrug and stop liking him, just like that. You’d be disappointed, just as you were the first time things went nowhere between you two.

But just as you did the first time, you’d get past your hurt feelings and move on (hopefully to a new guy who’s less of a fickle weirdo about his intentions). And that’s what you need to realize: even when things don’t work out, and you pursue someone who rebuffs you, having your heart bruised or broken will not kill you. In most cases, it won’t even slow you down for more than a couple of weeks. You’re more resilient than you know. And while getting hurt will never be fun, it’s a risk that you’ll find you’re willing to take—because as much as it sucks when things don’t work out, the way you feel when they do makes it totally worth it.

All of which is to say, I think you should ask this guy if he’s interested in you! I also strongly suspect that he would like you to ask, hence the way he keeps making loaded comments that beg for clarification. The door is open, kiddo; all you have to do is walk through it, by saying (in your own words, obvi), “Are you flirting with me, or what?”

Obviously, this takes a certain amount of nerve… although maybe not that much, since it’s not like your crush is a secret. Asking the guy if he likes you would just be hinting at something he already knows. But even if the worst happens, and it turns out that he’s been flirting with you just because he knows you like him and he likes the attention, at least you’ll know what you’re dealing with (a member the species jerkus maximus). And if it turns out he likes you? WELL, THAT’S FUN.

But before you do that, one more thing: the way your classmates bullied you for being black was totally repulsive, and I know it left a mark. But if you allow that experience to tarnish your expectations of every interaction moving forward—if you anticipate rejection at every turn, and assume that your skin color is to blame every time someone doesn’t like you back—you’re going to sabotage an awful lot of potential connections before they ever happen. Insecurity is awfully poisonous that way; if you’re convinced that nobody will ever love you because of how you look, it won’t take long before other people pick up on that and decide you must be onto something. So when you approach your crush, do it with confidence, with hope, and with the solid understanding that if he doesn’t like you, that’s his stupid problem. It means nothing about you or your desirability at all. And while it may take awhile for this to fully sink in, I promise you, someday in the not too distant future (perhaps around the time that you have access to a wider variety of social circles with a wider variety of people in them), you will realize not only that you have no shortage of prospects when it comes to dating, but that love comes to people of all shades and shapes and sizes—for no other reason than that they’re open to it and believe they deserve it.

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