How old are you, 16?
I mean, some men think that way but certainly not all.
Another clueless male checking in. I once had a woman spend an entire party trying to “get my attention” and was totally oblivious. I only found out about it later when a friend commented on my good fortune in not getting together with her.
And the less said about how I spent almost two years living with She Who Is Now My Wife without realizing that she was in love with me the better.
yeah we men are clueless alot of the time. i had a good friend who was madly in love with me for about 6 months before i figured out that she even liked me.
Can you do something indirect, like have a female friend talk to him and bring up the topic about the two of you dating w/o making it seem like you are the one behind it, like its just 2 people brainstorming?
Gotta agee with the majority. True story.
When I was 17 I worked at a Taco Bell with a really gorgeous girl named Mary. She also went to Catholic school, and so would show up to work in that uniform. She asked me to walk her home a few times. Told me she didn’t have a boyfriend once. Would practically walk on my right foot at times. Alwas greeted me with a smile and would listen to my dumb jokes. Never thought I had a chance with her.
After I got fired my brother (who also worked there) asked me when Mary and I were going out. I asked “She liked me”? He smacked me in the head.
Unfortunately its true, as men we are remarkably dense. The girl i am currently dating was one I was decidedly unsure about… I honestly didn’t think she liked me very well, so very early on I said “I really don’t want to bother you, if you don’t feel anything towards me, I’d rather know it now.”
Imagine my surprise when she grabbed the back of my head and gave me a rather nice kiss.
I agree with the light-hearted but direct approach. I would not start out with “I like you” because it could sound like “I’m madly in love with you.” Ask him out on a date. Make sure he knows it’s a date. Tell him that you value his friendship and don’t want to damage it, but you also want to explore other possiblities if the interest is mutual.
By downplaying your feelings as only being interested in seeing what the possibilites are, you are protecting yourself and the friendship if he does not want to pursue anything other than friendship. But it’s still opening the door.
I think this will help all of us understand the opposite sex a little better. 
Well, maybe not the men :smack:
Another guy here…
IMO it is totally up to you to make the move. If it’s already been 6 years he won’t make the move because you are now a “friend”. That doesn’t mean he’s not interested it just means he thinks it’s too late for him to make a move. So it’s up to you but please don’t give hints or clues. After 6 years he’s not looking for clues anymore. He’s probably resigned himself to just being a friend so any romantic hints will just leave him confused. It’s been said before. Men are stupid! Really! We are!
Just tell him straight out that you want to be more than friends.
I have an idea. The two of you go out drinking, assuming you’re old enough. After a fun night of drinks & laughs, when you’re both drunk, kiss him.
I can relate.
I gotta go with the group here and say “tell him.” Unless he is a huge jerk (which I seriously doubt, since you’ve been friends for six years) one of two things will happen: 1) he’ll respond that he’s interested in taking the relationship to another level, or 2) he’ll say that he likes the relationship as it is. He isn’t going to think you’re a freak for telling him. He’s almost guaranteed to be flattered, if anything. If he IS interested, he’ll be grateful to you for making the move. If he ISN’T interested, he’ll probably be more concerned with not hurting your feelings than thinking anything bad about you.
There really isn’t a downside to this. “Worst case” is that you’ll just stay friends as you are–which is pretty dang good “second prize”, sounds like.
Showing up naked with beer would be a bad idea 
You don’t want to put him in a situation where he either has to outright reject you or do something he really didn’t want to do to begin with. Since he likes you so much as a friend (plus he has a penis, which seems to dictate certain behavior at times), there is a decent chance he’d opt for the second, and then weirdness would ensue and the friendship would suffer. I’d say the same for the “or just kiss the guy” advice, for the same reasons.
Good luck. I feel for ya.
As I have been saying for years "women get about 6000 channels, but men have rabbit ears with tin foil on them and we only get 2 channels: hunger and orgasm, you generally have to feed us and/or f%^k us to gain our attention.
unclviny
I’d say tell him. The fact that he hasn’t made a move on you in uncertain terms means nothing. I’ve dated many of my male friends, none who ever tried anything until I made it clear I was interested, and all of them confessed (after the fact) being interested in me before that.
Between Opal and unclviny you’re getting good advice. Having been on the flipside, I gotta say " Tell him. In uncertain terms."
Then tell us how is went.
YOU have to tell him. His thoughts on the issue are probably “Huh?”
Look, here’s a rule. We’re not for analyzing. We’re very simple creatures. We don’t get hints.
Well, if life was a movie, I’d say, “Kiss him ‘spontaneously,’ next time you’re being touchy-feely, then act all embarrassed afterward. This will cause him to immediately re-evaluate the relationship, and he’ll show up and profess his undying love at about 2:30 that night.“
Unfortunately, in real life, ‘talk, THEN sex’ generally works better. Which is a pity, because most of the alternatives (mailing him anonymous, overly suggestive notes, say, with nude pictures that don’t show your face) would be a lot more entertaining for everyone around you.
This is probably going to be a bit awkward, but it doesn’t have to be that awkward, if you think it through in advance.
–You are the one who’s changing the ‘rules’, not him. Therefore, you’re going to have to take initiative.
–Do not be melodramatic. “I . . . think I’m in love with you!” or “Do you see me as a friend, or a woman?” This will activate the ‘oh, crap, how do I get out of this’ mode.
–Do not be confrontational. Do not blame him for not reading your mind. See ‘oh, crap’ mode, above.
–Do not be too forward. Not because he might loose respect for you, (he might, he might not. I wouldn’t, were it me) but because that confuses the issue as to weither you want a ‘relationship’ or ‘friends+sex.’
–Give him an ‘out,’ where he can say no without actually saying ‘I’m not interested.’
–Do not make it a big deal, even if it IS a big deal to you. This will not change his mind, but WILL make it considerably more painful to both of you if the answer is ‘no.’ Guilt-tripping someone into being with you does not result in a good situation. And it is profoundly uncomfortable when someone has strong feeling towards you that you don’t return.
–Do not bring it up at a time that will force you into close proximity to each other immediately afterwards, if the answer is ‘no,’ or ‘I need to think about it.’ This will not only be awkward, it’s going to rather forcibly remind him of what might happen if things don’t work out.
–Do not try to stack the deck by dressing too sexy just before asking. Men do not, generally, have that ‘brother zone’ thing where he didn’t even notice you were a woman. He has almost defiantly already decided wither or not he thinks you’re attractive. And despite popular opinion, finding you attractive does not necessarily mean he thinks that sleeping with you would be a good idea.
Best bet, after a night out, (or in, or whatever) as you’re leaving, say something like “I’ve been thinking, and I know this is a little awkward after all this time, but I’d like to try going out. Not as friends, I mean. Don’t answer now, you can think about it. Give me a call in a few days, if you think it’s a good idea. If not, you don’t have to say anything, and we can forget about it.”
At this point, assuming he doesn’t immediately say ‘Yes yes oh god yes!” He’ll probably have a baffled or horrified expression on his face. Don’t panic, though, that’s not his reaction to the thought of you naked, this is the aforementioned ‘oh, crap’ mode. It’s a reaction to an uncomfortable situation, not you personally.
Then leave. Wait nervously. If he doesn’t call you, well, sometimes things don’t work out. If you can deal with it, you can still stay friends. If you can’t, maybe taking a break from him will help. Worst case scenario, well, at least it’s settled.
If he ‘just friends’ you, (or worse, ‘I don’t want to ruin our special friendship.’ God, that ones insulting and humiliating, isn’t it?) cut him off with, “You don’t’ have to be like that, it was just an idea.” Proceed as outcome one.
Now, hopefully, he’ll like the idea, or at least want to give it a shot. If so, don’t get physical too soon. This is VERY important. Yes, you surely ‘know each other well enough’ by now, but you haven’t determined if you can work as a couple yet. Again, I’m not arguing from a moral standpoint, just a practical one. No matter how sweet he is as a buddy, there’s a non-trivial chance that you won’t like him
A few dates that ended badly isn’t much strain at all for an old friendship. It’s much harder to go back once a couple of nights of bad sex are involved, and everyone’s angry and humiliated.
Of course, that’s the best way. The less honest but possibly easier way, depending on how close you’re roommate is to him, to just have her ask him if you’re interested. In such a way as it seems like she’s an interfering matchmaker, not a designated representative. This can work but it might cause him to stonewall to avoid embarrassment. Make sure she lets him know that she thinks you’re interested, though.
How old are you both? I don’t mean that in a condescending way, but it might change the tactics a bit.
-spittake-
No, that’s basically the WORST thing she can say, especially if they’ve been friends for years. I have had women say that to me many times over the years, and have heard it said to several other guys. In EVERY SINGLE CASE, it was followed up with an unspoken, “but not YOU, of course. Just like you, but someone else. And maybe a little better looking.”
Ok, maybe “You’re such a GOOD friend” or “You’re like a sister!” would be worse, but not by much.
The reason guys are so bad at picking up ‘hints’ is that they are very rarely distinguishable from ‘non-hints’ in any measurable, testable way. 
–
“People don’t just ‘run into each other’ and have sex. This isn’t Cinemax!”
That’s why you want to get him drunk. As a confirmed pathologically shy male who has been in this sort of situation once or twice, if shyness is his problem, then giving him a chance to get frightened will be catastrophic. If shyness isn’t the problem, then do something else.
Another guy checking in. Being direct is your best bet. My GF was also my best friend (like you, for 6 years at that time, another 3 years of being semi-serious and discussing things and finally last year I asked her out).
We (men) are very dense sometimes and depending on the guy, he might feel that you’ll get all weird if he told you he liked you physically. I know that’s what I was thinking while I was just friends with my GF. She gave me some rather direct hints after I jokingly asked to see her bra and she took off her shirt in my car!
Treat us like cave men, we like it
Another guy here. First understand this:
We do not get the most obvious of clues
So, you have to talk to him, otherwise you’ll keep wondering “what if” forever. Set up a meeting just for the purpose of talking about it. Make sure you have plenty of time if needed so you don’t have to rush it. As mentioned it’s good if you can leave if need be, for example If he has not considered it or otherwise needs to think about it. Just say that you’ll call or meet him the next day.
Call him right now. This very minute. Just do it. Now. I dare you. Go on.
I’m sorry that’s been your experience when you’ve heard this. You’ll note that this is not the case in this instance (She really does like him but doesn’t know whether he likes her).
Would you mind if I grabbed this for a sig line?