As an official card-carrying male, I’ll say: tell him.
Guys these days are scared to put a move on a gal. We don’t know if she’ll go for it or if we’re gonna get kung-fu’d into the middle of next week and then maced and then arrested for sexual harassment.
And we are not prone to subtlety, unless it’s on the level of a thrown brick with a note attached or something.
In 5th grade I had a mad crush on a pretty girl in my class. I finally got over it by about 8th grade or so. We stayed friends all through school. (The preadolescent pining wasn’t as painful as it sounds, actually. Or maybe I’ve just blocked it out.)
Senior year she was voted homecoming queen. On the day of high school graduation, we were reminiscing in the music room and she said, “You know, back in 5th grade I had such a crush on you!”
:smack:
The point? Well, there are two:
Oddly enough, (or maybe not) one of the two things this thread reminded me of was being told in 5th grade that the girl I’d been sitting next to for 5 years (identical initials) had had a crush on me the whole time. I had too, but figured I was dreaming, that she didn’t like me, and that I wasn’t even on her radar beyond the kid she sat next to. (Also I was in 5th grade, but YMMV.)
As for the OP: tell him already. He’s dropping hints to your friends, and appears to be saying: tell me if she likes me, I’m to scared to take the first step.
Choose a manner that is comfortable for you:
light booze isn’t bad, some sort of way for a graceful come down on both sides would be nice, and the ability to say (should the unexpected happen and he says no) “how drunk was I last night, and what was I talking about?,” even if you weren’t and just want to forget it, can be face saving and relationship repairing.
A sounding out by Obsidian would be ok… It sound’s like he’s looking for encouragement to stop being a nice guy friend with occasional physical chemistry, and start being a nice boyfriend with… yeah 
Alternatively, this thread if full of good suggestions on broaching the topic.
BUT TELL HIM ALREADY. Having gone through this twice (I’m really 
, but it appears to be Y chromosone related.) I’d have liked a straightforward “Let’s date” to the messes that hampered one relationship and killed another.
CC
I’m bumping this (sorry) because a lot of people have taken the time to post and give me great advice (and boost my confidence to boot) and I hate people who start a thread and leave it to die. I’ve had the flu, only just got back to work and online and when cleaning out my favorite places saw that this had had activity since I thought it had died.
I have decided to tell him. He comes in on the fifteenth and I’m hoping to restrain myself from jumping him the moment he steps off the train. My plan of attack is this: he comes over to our house a lot in the evenings to have a beer, watch TV and basically hang out. So, one night when the stars are in alingment (kidding) I’m going to walk him out to his car and say “Look, we’re good friends and have been a long time, but I’d really like to be more then friends and sometimes I get the feeling you do to. If you don’t that’s fine and we can never mention it again. But if you do we should do something about it because we could be good for each other. You don’t have to say anything now, go home and sleep on it.” Then give him a kiss and go back inside. That way he has time to freak out and process without me sitting there. And if the answer is no then I don’t have to deal with the rejection or - gods forbid - the explaination of why I’m a great girl but. . .
So, I’ll definetly post and let you know how it woks out. Thank you all for your advice and stories, you have really given me the guts to just DO this. And reminded me why I love these boards so, so much.
Woo, go Pucks!
Excellent plan. Great job on the wording.
You can do it! Keep us posted - we’re rooting for you.
Well?!?!?!?!?!?
What happened? We’re dying to know!!!
I’m betting we need to be cueing the pr0n music about now.
As a male, I vote with the “just ask” contingent. Your plan sounds reasonable: “Here’s how I feel, how do you feel?” Or maybe the next time you’re snuggled up together might be the time to ask “what are we doing anyway?” You might be sending mixed signals that he can’t figure out.
But you don’t say anything about his interaction with other women. Does he have or has he had girlfriends that he talks to you about? What are those relationships like? Does he spend less time with you when he’s involved with another woman, and just come to you when he’s alone? Or are you a consistent part of each other’s lives? Has he introduced you to his girlfriends? How does he behave toward you when you spend time with other men? Or do you? Maybe he really does think of you as a big sister/old pal where he finds some stability while he looks for a partner. And if you are the only woman in his life, what does it mean that he hasn’t shown more intense interest in you in all this time?