DO i bite the bullet?

I find myself attracted to one of my closest guy friends. Both in our late 20's, so you'd think the maturity level would be higher but here it is.
I believe he feels the chemistry too, however there are complications, mutual friends getting in the way, some insecurity on my end, the fact that i've always been treated as one of the guys (most of my best friends are guys!) so crossing the line is a bit of a mistery to me, etc.
We've been friends for a few months and although we flirt its hard to tell if its just a friendly tease or more. Lately there is more physical contact hugs, backrubs, a sholder to nod off on during a long trip, and the occasional butt pat. Talking on the phone is a bit uncomfortable, but hanging out in person is a regular riot. There are also suggestive remarks and compliments. I know he must be seeing other women (although we don't talk about that!) but i can't help but feel that there is something more between us.
I've missed my chance to make a move twice already, call me chicken but i am afraid that i am completely wrong and will mess things up. Plus i am a bit old fashioned and would like the man to take the first step.
How do you tell if a friend would like to cross that line!? DO i bite the bullet and take my chance the next time oportunity knocks, or forget the whole thing and keep it light and friendly. I should mention that i do have a bit of a hang up about my weight(i am 5'4" & 170 but athletic, i work out, cycle, play tennis, snowboard, etc.), but i've met one of his ex's and she is bigger that me. :sad2:

I say find out if hes seeing anyone else right now.. Then go from there. You never know until you try....

Also ........its obvious he likes your personality.......at least as a friend. He doesn't find you revolting if he pats you on the butt and gives you massages....so don't worry so much about your weight..

no he is not dating anyone at the moment. at most he is having diner with coworkers, but thats all.

Well there you go! I mean its worth the risk. All he can say is no...... I mean just casually suggest the two of you go out sometime. If anything be kinda joking about it. If he rejects you be like........yeah I guess I was getting desperate....and just jokingly smile at him.....

Does he openly flirt w/ other people as well? Do you flirt with him? I mean he may want to ask you out but maybe he thinks you see him as more of a friend...... I mean the only way to find out is to try. I've learned you can't wait around for guys..... Sometimes you just have to take action yourself or your gonna be kicking yourself later on when he finds someone else.

Yeah, that old fashion crap is garbage!! LOL Sometimes guys got no clue as to what's goin on, a woman is just as capable of starting something as a man. Do you know how many of my good female friends I have that I never thought liked me so I figured "Why bother, she prolly dont like me..." then later I found out they have a crush on me and now its too late to do anything because they have b/f, husbands? LOL Its not 1930 anymore, girls can make the first move :)

BLAH!----"the fact that i've always been treated as one of the guys (most of my best friends are guys!) so crossing the line is a bit of a mistery to me, etc."

Perhaps that's how he feels about you. He treats you like one of the guys. He's comfortable hanging out with you. He likes your company. Do you really really want to broach the subject?
Drop a hint but let him make the move.

Ellynn: I like your approach. I might just give it a shot.
To answer your questions.
"Does he openly flirt w/ other people as well?" I've noticed that he will engage other women in conversations, however i've never noticed him acting the way he does with me. There is definately a more playful aproach where i am involved.
"Do you flirt with him?" Yes. At least in my eyes i do. Now, as i've talked this whole thing out to death ... it seams like i might not have been as obvious as i though i was being. Plus, i have to be resereved as there are others around and frankly i don't want them knowing of my crush just yet. :D

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Originally Posted by Chlorine

Perhaps that's how he feels about you. He treats you like one of the guys. He's comfortable hanging out with you. He likes your company. Do you really really want to broach the subject? Drop a hint but let him make the move.

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Its entirely possible that you are correct, thats why i am so conflicted at the moment. :( However, as there other guy friends around and in comparison to their behavior, his sticks out. Of course it could be all a figment of my imagination but he is definitely crossing that “friends only” line. Example: on a recent trip we all took together (there are 5 altogether, close friends that is!), I got a cuddle-me-up-in-my-bed wakeup call. He actually jumped in my bed and cuddled me until I woke up. None of my other friends will ever even walk into my bedroom without permission.

ahh - That is the best way to be woken up! I LOVE early morning snuggling...

Come on guys - tell her! You know you wouldn't be jumping in to bed with a sleeping woman if you had absolutely no interest, would you?

No, I can honestly say I dont think I would do that unless I had some interest in the girl, thats definately one point for you :) As a guy, if Im cuddling with somebody like that it's a way of showing I feel close to you on a mental and physical level, not just in a "buddy" kind of way either... it means I like you enough that I want to touch you and gettin snuggly in a bed with you would be my way of saying "Hi, its me, if you're having any questions as to how I feel about you, this should help clear them up... like windex... ok?" Unless of course somebody died and you were crying or something, but on a fun trip? Yeah, game on :)

He DEFINITELY sounds interested....like sum of the others said just ask him to go get dinner sometime, and that woudl give him a chance to make a move. Plus the fact that he doesn't mention any other women to you, makes it seem as if he doesn't think of u as one of the guys....

See i thought so too. :) I mean early morning cuddles are great signs in my book too.
However, to make things interesting: i just spend the evening in his company (no, not alone unfortunately!) and he was extremely quiet. I mean NOT his usual teasing self, cracking an occasional joke but definately not his usual. A friend of his is visiting from out of town so i did make an efford to make friends, good impressions, etc. But i don't know if that just made things worse. I also tried to be a bit more "obvious" in my behaviour towards him but it just seemed to get him even quieter(is that a word!?! :nerd: ). So here i am scratching my head going - well now what?! Totally mixed signals as far as i am conserned, i almost feel like i need to get him drunk to get him to loosen up. :horror: I don't mean to whine guys, just venting!

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Originally Posted by XPixiedustX

He DEFINITELY sounds interested....like sum of the others said just ask him to go get dinner sometime, and that woudl give him a chance to make a move. Plus the fact that he doesn't mention any other women to you, makes it seem as if he doesn't think of u as one of the guys....

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Pixie ... I've had boyfriends in the past who would make comments about good looking girls walking down the street to me, or discuss actresses and their attributes (so to speak!). (when in a relationship, although jealous i am not insecure at all!) So possibly thats why i don't really consider mention of such from him as significant. However, when you start discussing current, pending or possible relationships with other women/men thats when you are in the friendship zone, RIGHT?! I mean, its been a while since i've had a steady boyfriend, or a serious exposure to the dating scene (devoted the last 4 years to my carrier, after a really bad breakup!) but i think we all make comments when a nice "body" walks by. Heck, i know i turn back and stare at a nice male speciment, i'd wissle too if i knew how! ;)