For all you know that’s exactly why he’s not asking you out.
All we know is that YOU’RE the one who’s interested in him. You should ask him out.
If he spends time with you alone, if you are not in another relationship and he is calling you twice a day and he is not gay, then he wants to do you. Pretend to let him get you drunk.
Lol. hes not gay, I am not in a relationship and as far as I know, he isn’t. The problem is we are not alone. My teen has problems and cannot be left alone. I hope that may be what is hampering him, and I am working on getting a sitter. He usually seems happy to see me ( I don’t mean that, but a big smile, and always wants to help me out with something, hes very kind.
What the hell are you asking us for then?!
Let me tell you something that all people, not just women, need to know: nobody likes this subtle low-key game-playing shit. Maybe it’s fine in a flirty context when you’re both in on it, but this anxiety-ridden overanalyzing “does (s)he, doesn’t (s)he” crap is good for no one. Be blunt. Assume no one can take a hint. It will save us all a lot of time and trouble if everyone would just man the fuck up and take fucking charge. The worst thing that could happen is NOT the worst thing that could happen, IYKWIM.
Next time you’re together, and he says something that makes you laugh, say:
“Ha, ha! I really enjoy being with you, we should do something together!”
Eleven words. Say them sincerely but laughingly. Think of it as throwing out the first pitch!
That’s it, you’re all done. See? That wasn’t so hard, now was it?
Everything should be clear from here on in, one way or the other.
Be sure to keep us posted, of course, we’re all dying to know how it works out!
Hell if I know. I’m hoping this story is wildly exaggerated, or all-out false.
B, I can relate. One thing people are surprised to find out about me is I am horribly afraid of romantic rejection. Only romantic rejection, mind you; everything else, I’m like “Fuck it! I’m gonna be dead someday.” In the past I’ve found myself getting into similar mental mind games.
*Maybe I should say something if I like him so much? But what if he doesn’t like me back? Of COURSE he likes you back. How clear can it be? Well maybe I’m misreading signals, because if he did, he’d have said something by now, right? Maybe he’s as afraid of rejection as you are…
*
And so on. Guys ask me out, presumably because they like me, so why isn’t this guy asking me out? Must mean he doesn’t like me, right? Of course, this is pure silliness, but it doesn’t stop me from feeling this way. In college, I had a crush on a boy that damn near ate me alive. I just knew he felt the same, but the fact that he never acted was discouraging, so I never said anything. Years later, after the crush had long subsided, I admitted to a friend the crush I had on him. She laughed and laughed. Apparently the crush we both had on each other was visible to the blind, and she said she could never understand for the life of her why we never got together.
Because we were both chickenshit. Don’t be chickenshit.
My question is, what does he get out of it with things as they are now? I’m cynical so my first thought is he is using you for something and maybe I’m way off base, but it wouldn’t be the first time I’ve heard of it. I also agree with lavenderviolet that he is probably not looking at you as a potential partner.
Well, theres nothing to be used about me, I have no finances; he helped me get a temporary job that he had also back in May/June.
He got my teen a haircut back when when I couldn’t afford it and bought me some household items we were in need of. And no, I’m not using him.
Okay. Just looking out. 
Also, you should have a conversation with him. Rejection beats not knowing.
So between the two of you, there is 81 years of accumulated life experience, and yet…
Sounds like a whole lotta shakin’ goin’ on for an empty bottle.
BigBertha, you’re a big girl now. Ask him out. Though why you’d want to have an unemployed boyfriend is a question only you can answer.
If he rejects you as a sexual relationship, so what. You say you’ve been rejected before (haven’t we all!) and nobody actually dies from it.
It’s probably been said before, but if nothin’s happened by now, it ain’t gonna happen. Just because he’s nice to you, doesn’t mean anything more than he’s nice to you.
All this game-playing, over analysing seems like stuff you’d expect from a 19-year-old, really.
Maybe inside this mature woman is an immature one just dying to get out.
Truly. Make the moves to fuck him if that’s what you want, or make the moves to fuck off the idea that he wants you.
Oh, good, I’m not the only one thinking that. I feel like I’m being a little snarky lately so I didn’t want to say anything.
The other aspect is that he’s young enough to be her son.
Even so, it’s worth a conversation if it’s what you truly want.
Yes, there seems a curious subtext of “I’m not good enough” here, I think Silver Fire. Only BigBertha would really know in her heart of hearts whether she is a woman who misinterprets any attention from men as them paying attention.
That he’s young enough to be her son is probably not as bad as her being old enough to be his mother. Now there’s a conversation…
FUCK HIM! Fuck him right now!!
No, I just like him and was throwing this out there to see if maybe I can’t tell if someone likes me or not. I used to have really good radar on this. And are people saying someone who is unemployed should never be liked?
I think he should have a say in that.
Assuming he’s not out of your league, I think he’ll be more than happy to.
Being liked comes before that, young man.
So you gonna ask him or what?
To have sex? No. But I will be more proactive.
In the far, far, faraway distance of the micro part I see of you in this thread BigBertha (not that you are micro, but this being a small part of all of you; and on a forum) I think you’re radar’s shot.
If at 50, you have to ask a bunch of cybers if you “can’t tell if someone likes (you) or not” then, the answer is that you can’t tell.
Nobody said that someone who’s unemployed should never be liked.
I think that to make this assumption is being a bit immature. Only a teenager wouldn’t care if someone had a decent means of support or not, when considering the said person as a potential partner. As a mature adult, that the intended had a job would definitely be on my list of priorities.
Certainly we are very different people BigBertha and there’s nothing wrong with that - what you do, and how you do is certainly your choice.
For me, firstly I wouldn’t be interested in someone a generation younger than me - unless it was purely from a friends-with-benefits stance in which case not having a job wouldn’t matter in the least.
Secondly, there would be no ‘he should make the first move’ bullshit going on - he’d know what I wanted, and if it didn’t work out that way, big deal. From my perspective that’s no reason to kill a good friendship as well.
Thirdly, I wouldn’t be ‘taking a poll’ from a bunch of pretty much anonymous people; I certainly wouldn’t be wasting so much brain space on it. Hell, he wouldn’t be paying me enough rent in there for that.
Face it. He’s your friend because he’s probably a really nice guy and you’re good company.
Everything else you’re just making up in your own head.
Daydream if you like. Nothin’ wrong with that.
But if you’re not woman enough to have sex with him, then accept that what you have is what you’ll have. And if you don’t want to have sex with him because that might somehow spoil the opportunity for a ‘long term relationship’ then truly, there’s a planet out there so distant from what I know that I can’t even see it.