Editor’s note: This is an advice column written by in-house know-it-all Riley Brands. All answers are based on personal experience. Brands is not a licensed professional. Questions for Brands can be sent to [email protected]. 

Dearest Riley,
I have feelings for one of my friends who has been really supportive and good to me in the last year. I don’t want to ruin what we have, but I also care about him a lot and want him to know that. Should I say anything or play it cool?
Sincerely,
Friends or Something More?
 
Dear Friends or Something More?,
I know it’s hard to hide your feelings for someone when that someone is a close friend. You don’t want to risk opening yourself up because the gamble is so much greater than if they were a mere acquaintance. That said, if you really care about him, it will probably be immensely frustrating and unfulfilling to stay quiet while still remaining friends. Unless you’re the sort of person who can happily deal with the uncertainty, you should just be honest with him. Tell him how you feel in no uncertain terms and hope it turns out well. At worst, he can say he doesn’t feel the same way, but if he’s a good friend, he won’t run away. He may be a little withdrawn for a while, but you can take that time to re-adjust and move on from the idea of you and him as something more than friends.

If he does cut out, that definitely won’t be easy. However, it will call into question how good a friend he was in the first place. If, after all the support he’s given you over the past year, he bolts at the mention of a natural development of feelings, he either isn’t really a very good friend or is just less mature than you thought. Neither of those is the sort of person you want to be with.