Should I Tell Him How I Feel?

Question:

I’ve written you several times about my appreciation for the Alice series, but I have a quick question for you now about my own life. I’ve had feelings for a guy at my school for a little over a year, and we’ve gotten closer over the past few months. I took him to my Junior Prom in late March and had a great time. We danced to a few songs, didn’t kiss or anything, and he texted me telling me he had a great time afterwards. Since then, however, things have died down. We haven’t talked as much since then, and when we have, it seems really forced. He asked a friend of his (who didn’t have a date) to his Senior Prom, which, stupidly enough, made me like him even more–she wouldn’t have gone if she didn’t have a date, and she got to have fun before graduation this way. So here’s the thing–he hooked up with that girl at his prom, we’re talking less than ever, and I still like him a whole lot. We’re going on a theater tour through the school, and I’m wondering if I should tell him how I feel (he just graduated). I’ve tried “showing him” that I like him–texting him, talking to him in the hallways, and even asking him to my prom! I feel like I’m going to regret it if he goes off to college not knowing that I like him, but on the other hand, at this point, how could he not know? What do you think?

Phyllis replied:

Obviously, the guy himself is the only one who knows how he feels, but from what you’ve told me, it really sounds as though you’re a bit more “into him” than he is into you. I think he already knows how much you like him, and I think he’s a polite guy who did truly enjoy going to your prom with you, but isn’t thinking of continuing the relationship. Whether or not he invited a girl who didn’t have a date (this is sort of iffy territory, because obviously he wouldn’t have invited a girl who did already have a date), the point is he didn’t invite you (who didn’t have a date to his prom either, right?) I think you would be doing yourself, and a possible future relationship with him, more harm than good by coming on strong right now. He’s getting ready to go to college, he probably doesn’t want any entanglements back home, and perhaps if you back off a little and concentrate on simply being a good friend, interested in his plans, his courses, and waiting for him to reply before you email again, he won’t need to feel defensive and keep you at arm’s length. I know it’s hard not to let someone know how much you like him. This happened to me when I was in high school, and I still think about this guy once in a while, wonder what happened to him. But there are many good surprises ahead just waiting for you. Embrace life, as he is doing, and see what happens.

Posted on: June 15, 2010