Dear Dr. Date,
I seem to be having a problem here. There is this person that I have been friends with for a few months now, and we see each other every other day. Well, I seem to have fallen for him, hard. But, I’m not sure how he feels about me. He’s hinted at liking me, and I’ve had my suspicions, but nothing has happened yet. And I’m not sure if I should tell him how I feel, because I don’t want to ruin our friendship.
I’m afraid that once I do tell him, things will be too awkward between us that we’ll have to stop seeing each other. So, what do I do? Do I just tell him? And if so, how do I go about doing it?
I know that he won’t say anything to me because he says that he doesn’t like confrontation, so there’s a chance that he won’t ever tell me, assuming he does like me. Which I’m almost starting to doubt now. I’ve never met anyone like him before and I don’t want to lose what we have. So, Dr. Date, help me figure out how to tell him without losing him. Help!
— Wondering

I’ve seen this situation quite often, sweet. It can end in any number of disastrous ways, but it could also work out great. Let’s try to avoid the disasters first.
Scenario one: You tell him you’ve got a thing for him, he freaks out and never speaks to you again. Not too likely. Look, all friendships contain some element of sexual curiosity. I guarantee this guy has at least thought about kissing you. If he is only interested in being your friend, he’s a pretty cool guy and he won’t let your adoration stand in his way.
Scenario two: You don’t tell him and remain friends for years, painfully pining for him through all of his dumb relationships, sorrows and joys. Over time this doomed preoccupation slowly turns into a way of life to which you simply adjust. You end up living alone with cats … lots and lots of cats. Seriously, I’ve seen this happen too often with both men and women.
It’s time to choose your own adventure. Which scenario do you prefer? I’ve known individuals that still choose the second scenario for some silly reason. I urge you to opt for the first scenario, which presents new problems.
You need to let him know that you dig him as more than a friend. The longer you wait, the more likely it is that he will abandon his secret hopes of dating you. Most likely, he feels the same way about you, but because of your guarded freakish actions, he can’t tell if you like him. Don’t you see the irony! He’s afraid to tell you because he doesn’t want to scare you off. Someone should break this painful deadlock and it might as well be you. Kiss him! Kiss him!