That IS an overture! Just go for it!
Judging from the picture you posted to the photo gallery, you can’t be much more than 25. What is he, 17?
I think that was the wrong picture. I am 50 and he is 31.
Be aware that he might not know exactly how he feels about you, and what you’re seeing are signs of ambivalence. Sucks, but there it is. I knew someone like that in college. She made it plain a hundred ways that she was interested, but I was attracted, kind of, sort of, not really like that, but sometimes I was. Eventually she found someone way more mature than me and moved on. Good for her.
She said that *while *biting his lip? “Rount roo reel th rassion?” doesn’t sound very romantic, to me. Unless you’ve got a thing for Scooby Doo.
Mmm, Scooby Doo. I mean, no, that’s just wrong!
Two months later, and you’re still doing the same dance? Ask him out on a date. Do it. Do eeet!
“Sweetie”? He is so totally into you! You need to wear a skirt next time you meet and no underwear, so he can take you right at your desk.
Damnit, Miller! Stop making me choke on my lunch!
I’ve always believed the guy should make the move.
While some people do have age gap relationships and some guys do prefer older women, I think typically a 31 year old guy probably would not be thinking of a 50 year old woman as a potential date.
If I were you, I’d try asking him about his opinion of age gap relationships or even try asking him if he has ever considered what it would be like if you and he went on a date to see what he thinks about the possibility. It’s possible that might even get him to consider it where he hadn’t before. However I just think it is UNLIKELY (though by no means impossible) that he would be thinking about it on his own.
What do you value more - that belief, or the prospect of dating him?
I thought you women were all liberated and stuff now.
I’ll tell you the same thing I’d tell a guy friend of mine in the same situation: stop being a wienie and just go for it.
I would assume he would ask me, if interested. In the past, theres never been one "move-maker’. I would be interested, the man would be, we’d give hints to each other til we realized we were both agreeable to dating and then we’d go out.

“You know, I like being friends with you, but I’m also kind of enamored with you, so if you’re interested in something more than friendship I would like that. And if you’re totally not, let me know now and I will transport us back in time 60 seconds so this conversation never happened.”
/takes notes
And back to add…If you want ‘the guy’ to make the first move <in quotes, cause I don’t mean THIS guy; I mean ‘the guy’ that you IDEALLY want> then I don’t see any problem with moving on and finding something a little less complicated. Enamored is good and fun; overly pain-in-the-ass is not, unless you’re in a slow and bored phase and just want to stir some water and see what swims up to say ‘Hi!’.
And back again, to add something that no one has mentioned, but…A 31 year old is thinking of sex. Lots of sex. He’s used to having it, and knows what he wants, and would LOVE to prove he can still bring it <something about ‘30’ just seems to throw guys into a mini-midlife crisis> If he isn’t trying it out with you, he’s trying it out somewhere else already. So, I wouldn’t become too ‘enamored’ with him, unless you are ok with something cute but casual. And yes, this is from a woman in her mid-40’s who has nearly ALWAYS dated far below her age, simply because interests mesh better there. But…only short term ones.
So go for it, but even if it clicks, don’t take it too seriously unless it does get very serious.
/2 coppers
Hmm. Some good advice here. He Did tell me to come over anytime (he is free most of the time as he is unemployed), so if I actually came over without my teen, maybe…
(yes, my teen is usually with me when I’ve hung with him).
Yeah, I wouldn’t expect a guy to make a move on me if my teenager was with me. If he really is interested in you, I wouldn’t be surprised if that’s holding him back, though I do agree with the chorus telling you to just ask him on a date. I’ve known some guys that get tired of being the ones always making the first move, and ALWAYS being the ones to put themselves out there for rejection, and decide to stop doing it. Let’s say thats the case here, you’ll just keep waiting for each other to do something and never get anywhere.

I’ve always believed the guy should make the move.
Why???
Please explain this ‘should’. Would you find it humiliating to be the consumer instead of the desired item? Below your status as a female?
Is it the opposite, that you consider it to be a man’s world and a man’s privilege to select and women should not be so audacious as to intrude upon it?
Is it simply one of those ‘GEE that’s the way it’s SPOZED to be’ things, like driving on the right in traffic, where you think it would just be confusing if we didn’t have the nice orderly scripted roles and everyone staying within their role even if they are arbitrary?
Is it a ‘what will people THINK’ thing where you would conjure up an image of yourself that you would not like if you were t be the initiator? Or even literally fear other people saying things? Does age come into it here? If you were the male and he the female would you expect the younger female to be the initiator or think badly of the older male if he made a move here?
I haven’t read the thread, but saw thisand thought of the thread title. Link to UserFriendly comic strip. punchline: I treat [women] like compilers. They take simple statements and make them into big productions.

Why???
Please explain this ‘should’. Would you find it humiliating to be the consumer instead of the desired item? Below your status as a female?
I’ve had enough rejection in my life. in my youth, I always let guys know I was interested, and they all were not interested and told me so in unflattering terms.
When older, I would, like I said earlier, give hints if I was interested, if they were interested, they would take these hints and ask me out.
Why ask if you think the answer may be no is my feeling.
If interested, I think he should ask me out, although with neither of us driving, it limits where we can go on a date, though I have always been low maintanence.