Why won’t he ask me out when we’ve been texting for a while now and it’s clear we’re attracted to eachother?

[Anonymous]

First off he’s not a mean guy or anything, just really quiet and doesn’t seem social. He lives in my building. I’ve seen him sitting alone a lot out places and never with a girl. We have a 20 year age difference. Anyway once I dropped all my groceries and he helped me pick them all up. But he just texts me to flirt. In the past he’s told me he’s worried he makes me uncomfortable. I have cleared this up several times so he knows I’m not.

[Anonymous]

I find the story a bit hard to believe, but I'll treat it a bit seriously for the sake of answering. I'll put myself into what I imagine the shoes of an antisocial 45 year old lonely man with possible self esteem issues. I will assume he is indeed single.

I would feel lost, wondering what I'm doing with my life, or at least occupying my thoughts with work or something else so I don't have to ponder it. My youthful years are behind me, and now I've gotten to that "undesirable" age. I feel old already, and I am expected to go about three more decades? It sucks.

The nice neighbor girl texts me sometimes, and it makes my day. It makes my day so much, that I put her on a pedestal and worry about being creepy or pushing her away somehow, so I back off a bit to compensate and let her breathe. Besides, she's two-whole decades younger than me. I was working for three years already by that point, and she had just been born. I understand that's an "adult," but we're at two different stages in life, and I don't want to drag her down.

But, she still texts me, so I'm going to be polite and text back. At least someone's checking in on me besides whatever family I have left.

I've lost all self confidence, and I do pretty good at hiding it, I think. I don't want the stigma of hooking up with a younger chick, at least not one that far away. I won't let myself dream of that possibly being okay to do.

[Asker]

You’re into something here. Interesting analysis. I don't know what to really do. I’ve just assumed he doesn’t like me at all and likes someone closer to his age.

[Asker]

And why is this hard to believe?

[Opinion Owner]

Well, I'm not saying that's exactly the case here. He's an entirely different person than I am, and the thing we have in common is the antisocial, loner behavior, depresso espresso. He's lived longer than me so maybe he knows something that I don't. Maybe he's found peace in life already and doesn't want to complicate it with a relationship. I have no idea. It is possible his tastes have changed with age as well, I prefer women about 6 years younger than me to 7 years older than me, and I'm basically 30. If I was magically basically 45, it might range from 8 years younger to 8 years older or something, who knows lol.

And the reason I found it hard to believe is because if I was that age (because his personality sounds similar to mine), I'd think it was a miracle anyone liked me at all.

[Asker]

That’s interesting. I really like the thought you put into this. I think is also possible he doesn’t think I like him at all genuinely. I model so maybe he thinks other guys are always asking me out. But it’s weird cuz he’ll text me every once in a while and it gets sexual. He voluntarily sent me dick pics last night and also said he would love to do something in person soon.

[Opinion Owner]

Okay, then I have a different image of this guy in my head now, because I get shy about sex outside of a relationship, and within the first little while of beginning one. I probably can't accurately describe anything any further about your neighbor.

But I will say maybe you shouldn't let his offer to meet up go to waste. Remind him about it once a week until it either happens or he changes his mind.

Texting isn't cutting it, you two should hang out for at least thirty minutes, even if it's not a date, just chatting in the hallway nearby. It's annoying to not know where someone stands. "Do I have a chance? Or is he just not interested?" is a question rarely answered quickly by reticent men.

[Opinion Owner]

Also yes he might think you are out of his league. That's something I'd worry about, usually.

[Opinion Owner]

And by sex I mean I don't send dick pics either. I've never taken a picture of it for any reason. They're ugly to me, why would I want to share that?

[Asker]

He’s a successful guy/a doctor so I bet he gets a lot of women. I just think maybe he’s worried I’d just meet someone younger and hotter than him. Older guys worry about that as much as older women.

[slatyb]

Because of the age gap. He assumes that you wouldn't be interested in a relationship. Ask him out yourself.

[spartan55]

How is it clear to him that you are attracted to you to him?

[Asker]

That’s a good question. I mean I tell him he’s hot and cute whenever he sends selfies.

[spartan55]

Meh, that's probably not enough. He probably thinks you are just being nice. Or you are just placating his ego.

[Zenpanda]

Why haven't you asked him out?

[Asker]

I don’t think he likes me. I’ll just forget it.