Guys - How would you feel about a confession letter?

Has he had a girlfriend since you've known him?

If he hasn't, I be more inclined to say something/write him a letter.

And the more pressure placed on the whole event, the more I would assume he was going to be like "Okay, what just happened" rather than going with the flow of something. There are a few things you can try. Like you can try giving him a kiss on the cheek or something in a cute way and see if he does something. That might seem odd, I'm not sure how you'd pull it off. Or you can try talking to him and saying something like "You know I'm going to be moving this fall, and to make the best of this summer I wanted to spend more time with you." Yeah, I'd say something like that. And maybe write a short letter just in case he didn't get the hint.

First of course it would affect your friendship , that's for sure, the other point you made that if he would be interested he would already do something , yeah that's true as well, but if he is a little bit shy, the letter you want to write is a really good idea.

but don't make to formal , and find a good way to give it to him and a good time as well, if he likes you like a girl he will be really happy if only like friend he will be happy anyway and maybe start to like you like a girl from that time in both way I think it is a good idea, if he is a nice guy of course and one more thing write it smart , not to much you want him just to know that you like him more than a friend but anything more than that you need to tell him in his eyes if he likes you as well, you don't won't to lose that and write all of in a on big letter . :)

No offense, but I don't think I've heard of a girl giving a letter like that since high school. And even back then I don't remember it ever going well.

I would wait until there's an occasion where you would both be drinking. Like a graduation party or something? And then kiss him. You'll be able to tell if he likes you then, and if he reacts poorly you can always blame the booze. I don't know if that's great advice, but it's worked for me. And I know there's a certain amount of awkwardness in just kissing someone, but I think it's less awkward than dumping a love confession letter on a guy.