Hey Mr. Cool!!
(I am looking over my shoulder for a cool person somewhere)
So I have a weird problem. There's this guy. Who else? You irritating creatures, you. No offense. He's perfect and sweet and blah blah blah, right? Here's where it gets tricky: we're friends with benefits. Not flirty-texts-and-holding-hands-under-the-table, but actual FWB. I've gone a lot farther (or is it further?) with this guy than I've ever gone before.
Which is fine, etc, but there's one problem. He doesn't like me. I mean, he likes me as a friend, and thinks I'm hot, but he doesn't like me like me. And, needless to say, I like him.
We are getting closer and recently got a LOT more physical (wonder if you can guess what I mean?) and I'm starting to feel a little weird about this. I feel like I shouldn't be having my first time doing important things with a guy who doesn't even care about me. I'm not stuffy or anything, obviously I see nothing wrong with FWB. But I'm wondering if this relationship is completely healthy, considering I like him, and he doesn't like me back.
I think I could be falling in love with him. We've been doing this for about six months, which doesn't seem much to you, and it isn't, but it feels like more for me. Also, I am having a blast with him!!! I feel so confident and sexy around him and he makes me feel protected and safe. I'm enjoying this so much, but at midnight, that tiny, irritating detail always comes back to me: he doesn't like me back. He has no feelings for me. And it bothers me, because when this ends (and it will, I'm not stupid enough to think it wouldn't, even if we were serious), it will rip my heart out, and he won't even care.
And, to make it more complicated, we go to a strict boarding school and there's absolutely no sexual activities allowed. So it's a lot of sneaking around. And if I get caught, I'm kicked out. And let's just say that my parents will cut my head off, stick it on a pole, and use it as a lamp if I get kicked out.
So what should I do? Continue this really fun relationship with a guy I really really care about? Or should I end it before it spontaneously combusts?? Or maybe, just yell YOLO like a stupid, uncreative teenager with no vocabulary and rip my pants off?? Why do I have a feeling you'll choose the third (it'd be way more fun)?
Thanks!! And you're really cool, by the way. And no, that wasn't flattery at the beginning just to make you read this ;).. How could I ever be so manipulative? *wink*
This will be a pretty serious topic, at least for me! Normally Auntie gets the Serious Business questions, which is ideal, since I spent my teen years going "durr, what is a lady." With that in mind, I will answer your easiest question first: it's "further." I learned this from an English teacher who was shaped like a bowling pin. "Farther" applies to literal distance and "further" applies to figurative distance, so unless you were literally running around with this boy, for many sexy miles, then it's further and not farther. I'm glad we could clear that grammar issue up before getting to the sexitude.
Now, as for your real issue: it's not stuffy of you to wonder about the value of this relationship. It's human. I apologize for dragging evolutionary psychology into this—I always concede that it might just be crazy psychological voodoo—but if you believe that field, almost everything we find attractive is borne out of a desire to mate. Much of what we like about each other comes out of a weird place in our lizard-brains that's preoccupied with child-rearing and family maintenance. No organism ever wanted a dude who messes around with you on the couch and goes home thinking that you are terrible. Obviously, that's not how we think about relationships in the modern world; guys who gawk at a hot actress are not thinking "Boy, I wish I could provide food and shelter for her offspring!" I'm only bringing this up to make the point that it's not "stuffy" of you to want something more than random whimsical sexytimes. It's totally normal to develop serious feelings in these situations (if anything, I think it's the purely FWB relationships that are the outliers).
You're also not wrong to enjoy this whole thing despite its flaws. Most high school kids—heck, most humans—mope around thinking, "Wahh, I suck, if only a hot person would look at me accidentally!" If you like someone, and he lusts after you, that feels awesome. But it also feels awesome to eat, like, three whole cheesecakes. Until it doesn't, and you're like, "Oh no, blehhh."
On top of that, I know this kind of relationship can be great because you're through all of the awkward dealing-with-a-stranger parts. Six months is pretty long for high school, and feeling safe around someone is nothing to sneeze at; each of you knows what the other is thinking at this point. Otherwise you're back to first dates where the guy leans over, and you think he's trying to kiss you, but he's actually whispering "CAN I HAVE SOME OF YOUR POPCORN," and then you kiss his eye and he has to go to the hospital. There's an allure to staying in a relationship where things already work smoothly.
Anyway, you seem to think I'd have supported this FWB deal, and I sort of could, but only insofar as it lets you comfortably work your way into the physical side of things. The moment that you want this to be more than what it is, and he doesn't, ABORT ABORT. These things never turn out well when one person wants the relationship to be more than the other person does (which, in my personal experience, is always). It's good to have fun, but you can't really call it "fun" when he's like, "Smell you later, idiot!" and slams the door, and you quietly whisper "I love you too!! :3" and off in the background your parents are plotting to behead you, apparently.
I know you like this guy, but if you're sure he doesn't return the sentiment, I think you should end it. There are friendly ways to do this—for example, by saying just what you've been thinking. ("I might be getting too involved here; I had fun, and I like you, but I want us to stop.") Doing this will suck, but come on; otherwise you're in a position where you're constantly intimate with a dude who would have no qualms about going after some girl he actually loves. And that would feel much worse than ending it amicably, on your terms. There are billions of dudes in the world, and as many as dozens of them are not terrible. What you deserve is one who actually likes things about you that are not just the lady things.