Guys: What's going on here?

[Nicam]

Back in 2004 I met a guy through mutual friends. My best friend ended up marrying his friend, and although this guy and I always had a crush on each other, we were never in the same place at the same time while we were both single. I actually started a relationship with someone else around the time that we first met, knowing he liked me (I was young and stupid).

Our mutual friends all say what a cute couple we'd make and have been trying to hook us up since the very beginning.

Well, we have recently been reunited and are living together as roommates with our other friend. We are both single. We flirt and tease each other all the time, do almost everything together, talk about everything under the sun all night, and even sleep in the same bed a lot because he has a TV in his room and we watch the same shows. We are also planning on getting a place together, just the 2 of us, as roommates, next month.

The problem is I like him as more than a friend, and I can't tell if he feels the same way or not despite all of the flirting, teasing, and quality fun time we spend together. He has not made a move although I would love for him to! I even sleep in his bed in my underwear. Come on!!! I'm trying not to be too obvious, but just enough to let him know.

Some more details:

Not to brag, but I am hot. I take good care of myself, and even model on the side. He has always been good-looking, and professionally successful, but this past year his company went under and he is now super-depressed. He no longer has the disposable income he's always been accustomed to having, and he has gained quite a bit of weight, about 30 lbs or so due to the depression. I don't care about this, because I've known him for a long time and know he is brilliant and one of the good guys and will come out on top. He's even lost 10lbs since we've been reunited. I just think maybe him feeling like he has nothing to offer and being so down on himself might be holding him back.

I do have a lot of guys trying to date me, which I do not flaunt in his face, but I always try and analyze his reaction to this. Just last week one of the guys at his office talked about wanting to hang out with me, and he said some unsavory things about him (maybe good?).

I'm not the type of girl to make the first move, I like to let a guy do his thing and pursue me. I also realize this situation is complicated because we live together. I don't want to rush things, but I am having a hard time playing it cool!

Any input or suggestions? How can I tell if he likes me as more than a friend? How should I play my cards here?

Thanks, fellas!

[Yet another guy]

Come on!!! I'm trying not to be too obvious

There's the mistake you're doing. Learn from it, please You can never be too obvious.

I just think maybe him feeling like he has nothing to offer and being so down on himself might be holding him back.

Yeah, I'm guessing that his depression is playing a major role in the relationship between you guys. He probably doesn't think that he has a chance with you - or with anyone else if he's really depressed. Knowing that others are pursuing you is only making that worse.
He might believe that he's trapped in your friendzone as well.

Any input or suggestions? How can I tell if he likes me as more than a friend? How should I play my cards here?

Flirting, teasing and all that certainly makes it seem very likely that he's into you and interested in more than friendship.
To find out if he really is, you need to communicate. And by that I mean, talk to him and ask about it.
Or alternatively, gather your courage and make a move yourself and see how he reacts. If he is interested, he'll be delighted.

Good luck with you guys

[bulrush]

Any input or suggestions? How can I tell if he likes me as more than a friend? How should I play my cards here?

Ask him. He may not be in the mood for dating if he's real depressed. Sounds like he is a huge risk-taker, he failed, and now he is penniless. Sound like a good recipe for a long-term relationship? Well, you decide.

And if you are not the girl to "make the first move", nor will you talk to him, then you are stuck in the winds of random events, and will never realize your dreams.

Sounds to me like you lack confidence, and I've been there. How about if you make a change, and make the first move on him? Tell him you want to date him, see what he says. Be sure to point out his good qualities to boost him out of his depression. He is probably thinking he is a complete failure with just one failed company. If he doesn't work out, for the next 6 months, approach men you like and simply start up a conversation. Get their name, do small talk, then ask them on a date. If you ask them on a date, the asker pays. Just sayin. Don't be a cheapskate. Real men hate that. Men who want to control you, want to pay for ALL the dates, well, that's just generalizing. But watch out for that.