So a little background to this story. I come from a really really small school, and I have the misfortune of of that school being predominantly Mennonite (for those of you who have never heard of the Mennonite denomination, think Amish with more electricity and brighter colored clothes) and highly homophobic. The last guy who came out of the closet as anything that wasn't straight as an arrow had to change schools because he was so bullied; hence my un-outed status. But despite all this oppression, my heart was fearless. I fell in love with this boy, let's call him Rory. Rory is cute, sweet, artistic, smart with a dash of nerdiness that made him irresistable. (Also did I mention in the right light, he's a dead ringer for Taylor Lautner?) Anyway for three odd years, I held a major crush for Rory and never told anyone. I did all that I could to get close to him because as a friend you find you're in the best position for secrets (say a secret desire for one another *spoiler alert* which didn't happen */spoiler alert*) but I always wanted to be so much more. As I was chasing the ghost of "might be bi-curious-ish" one of my female friends, we call her Mara, had been looking to date him for even longer than I had. I wanted Rory, but Mara stood a much better chance because Rory's track record is female dominated, so like a good friend. I matched them up. It made me feel wonderful to see Mara and Rory happy but at the same time I was devastated. My other friend saw a marked change in how I acted. I told them it was just a crush that didn't pan out, but never explicated. Months later, I was back to normal again, but still a bit down hearted about my love-life. A few weeks ago Rory and Mara broke up as high school couples do, and then not to long ago I saw Rory for the first time since the break and everything came rushing back. Suddenly I feel the need to tell him everything as next month, I'm going to college and will not have to suffer anything from the bigoted community I grew up in. This is where the advice comes in. Do I tell him or do I just let him go like I did the first time I was this close to telling him about me? P.S. Sorry for the book, but a situation this complex never fits in 140 characters or less.
Hi! Welcome to Empty Closets! I don't know enough about Rory to answer, really. You say the community is homophobic, but is HE? This is an important question. I usually recommend coming out first, and letting that sink in for at least a little while before confessing your feelings for the person in question. It's just a lot to spring on someone all at once.
What would Rory gain if you tell him? If he's homophobic, he might feel threatened and react badly - the end of a beautiful friendship. If he's accepting, he might still not be interested and that would hurt your self-esteem. If he's questioning, it might mean you go away to college leaving him "wishing" he'd know longer and had been able to act upon it. I understand you desire to unburden yourself and make a clean breast of things before you go away to a less difficult environment BUT I would want to ask you whether it might not be better to keep this as a beautiful memory, a secret crush which remained unrequited. I would ask you to think about what Rory will gain from your honesty - are you thinking enough of his feelings? Not saying DON'T, just saying THINK about it from his perspective first. Good luck!
