Yes. It's called fishing. He asks you out, but in a casual, non-commital way so that if you say no, he has deniability: the "I was only joking" excuse. It's a pride thing, and you know how guys are about pride.
If you ever said yes, something tells me he would jump at the chance to go out with you. Maybe he thinks one of these days you will change your mind and give him a pity date at the very least. You need to dispel that notion.
No girls like him because he's a big fat whiner, sounds like. If his behavior bothers you, I suggest you be honest with him. Tell him you care for him as a friend, but have no interest in dating, so he should focus his romantic energies elsewhere. He could be missing out on dates while he's barking up your tree (although I doubt it).
Maybe you can help him. Do you have friends you could fix him up with?
I don't know how close you two are, but you might also consider explaining to him that most women aren't attracted to mopey, "poor me" guys. Obviously you'd need to choose your words carefully so as not to offend him. I'm sure he's a good guy, but somebody really needs to tell him to grow a pair or he'll never get laid.
Love the tags on this one! I bet he is, too.
Without a doubt. Not that there's anything wrong with that.
I know someone like this. He is a really gloomy Eeyore. He has changed jobs and moved a few times because he keeps saying there aren't any women around who will date him. Moving to another location doesn't help him, of course, because he's the problem, but he doesn't want to hear that. Just a little self confidence would make a world of difference for him. It's sad, really, because he does have good qualities, but no women can see them because they can't get past the whining and complaining that he does.
This guy needs some tough love; tell him how it is and don't hold back. He's a man and needs to start acting like one.
This has happened more than once? The guy is holding a torch for you and you need to quelch it STAT. You're not doing yourself or him any good by beating around the bush. Sure, things may be awkward between you two for a while, but it needs to be done.
Or he could be desparate, wanting to get a date any way he can. Totally sucks for the girl!
If I were the crafty type, I'd crochet "Somebody really needs to tell him to grow a pair or he'll never get laid." onto a throw pillow.
It's funny 'cuz it's true!
hahahah omg that was too funny!
I'd buy it. As a gift, I mean. I don't need it.