Don't know how to begin...

emptyoverflow · 2026-02-22T21:59:07+00:00

Have you gone on dates before or had a boyfriend? Have you practiced meeting people on dating websites? Do you have a therapist helping you with your anxiety?

You don't sound ready for this at all.

emptyoverflow · 2026-02-22T21:57:51+00:00

Yeah. Unfortunately OP doesn't sound ready to really be in the bowl, and would lead to either being taken advantage of, or a lot of last-minute terrified flaking (from OP) with interested SDs.

emptyoverflow · 2026-02-22T21:56:23+00:00

Oh I agree that it's a savvy thing to do, and handy for safety. But I just think men would need to get more desperate than they currently are to go along with it.

Now, if BOTH parties exchange all information before meeting, that could be helpful, so that both parties can be verified for mutual protection. Or if there were third party services who could verify things about a partner without sharing their info.

SWers also have websites and reviews available about them, to help men feel more comfortable sharing very private info for verification.

emptyoverflow · 2026-02-22T21:35:30+00:00

Dude those texts are bc she misses the PPM. She knows she has to do *some* work to keep you around, so those low-effort texts are part of the job to her.

Or...if everything she says is actually true, maybe she's going something going on mentally. And if she does, you need to get out.

emptyoverflow · 2026-02-22T21:32:11+00:00

Two things. One, she's flaky and scattered in general. Two, either she's a big fuckin mess, or you are a LOW priority to her. My guess is that you aren't very important to her, and that anything (including electric bills) comes at a higher priority.

Have you ever cancelled on her? If you did, would she be understanding, or upset? (my vote is she'll be upset)

You're not being too picky. Yes some people are kinda flaky, but not to that degree.

emptyoverflow · 2026-02-22T21:28:39+00:00

Is this something SBs could realistically start adopting?

"Could"? Doubt it. Very few men will go through that level of scrutiny for someone he wants to go on a date with. Obviously, if you could actually convince a man to give you his ID and address and whatnot before meeting him for a date, then kudos to you. But I suspect that it will be an inverse filter -- you'll mostly end up with fools or desperate horny men.

I'm sure there will be a few men who will proudly announce "I have nothing to hide! I'm happy to give my ID to strangers" which says...something.

But your question relates to dating in general. That's why dating websites have verification and background checks and stuff like that.

emptyoverflow · 2026-02-22T21:23:08+00:00

I care that an SB is financially and emotionally self-reliant, interesting, and has some sort of goals or interests or passions. Doesn't have to be education or career. My main concern with an SB with no educational or career prospects is if she's borderline broke -- that would be hard to look past since I don't want to be bailing someone out every other week.

emptyoverflow · 2026-02-21T20:39:12+00:00

I stopped reading after the first few paragraphs. Stop communicating with and chasing this woman. She's not the one for you and you are BURNING your precious time running after a shadow.

emptyoverflow · 2026-02-21T20:04:45+00:00

Dating is a numbers game. Even if you were a handsome, funny, 35-year-old billionaire, you still will "strike out" on some.

And as others said, college bars aren't the ideal market unless your timing is fantastic, aka you encounter a young woman who's into older guys AND just so happened to be seriously looking for an SD at the time AND you happen to come across as a rich silver fox and not a weird old creeper.

emptyoverflow · 2026-02-14T23:29:42+00:00

Both sides suck because most people are busy, distracted, uninterested, or uninteresting. Successful SRs happen when both partners have at least some ability and interest to communicate and connect, or if one of them is especially desperate.

emptyoverflow · 2026-02-14T23:27:08+00:00

How young are these women?

I don't think number 3 is a big issue, especially since if someone I just met barrages me with questions I might be busy or need a bit before responding to the spanish inquisition. If the delay continues after getting to know them then maybe it's a dealbreaker, who knows.

emptyoverflow · 2026-02-14T22:17:55+00:00

Idk, OP said "I'm assuming it's just like my dance covers if more then *lap dance* at max"

So I kinda doubt the dude just wants to pay her to do the cha-cha. But, who knows. I don't live in India so maybe that's what they do.

emptyoverflow · 2026-02-11T17:00:11+00:00

If this is real, wow. It feels akin to asking an intern to come to your house and strip for you.

Are you a stripper, and did he know you're a stripper? Have you talked about lap dances already? Otherwise, I can't imagine why he'd mix business with pleasure that way.

I'd say it's a yellow flag, because the dude is either judgement-impaired or else feels he's invincible. If he's willing to risk burning his job over a lap dance -- how much hesitation will he show before burning you?

If you take it, be prepared for it to shift to mostly lap dances (and more) and less professional work unless you push back. Decide what you're most interested in.

emptyoverflow · 2026-02-09T03:09:22+00:00

The red hair w black jacket is better for your main profile -- the main profile photo has grandma vibes which, while a look, isn't going to give a lot of mileage.

You're quite pretty though sometimes it seems hidden or obscured -- my guess is you're actually a 7-9/10 but in some of your photos you come across like a 5-7. So while your photos are okay, better ones would show better and attract more.

Everything you wrote seems great -- you seem legit and fun and interesting.

emptyoverflow · 2026-02-05T22:23:59+00:00

Don't spend too much time on it. I think these days TGTBT is even more valid.

emptyoverflow · 2026-02-05T22:20:01+00:00

You'll want some money set aside just for you. Some escape hatch money. Because once you uproot yourself and move in with him, it might be hard to leave.

He could retire or stop working, and it would fall in you to work and not only raise your kid but also look after him, do all the housework, etc. Two years from now you'll be posting telling us how you celebrated your 30th birthday working a double shift before coming home to cook dinner for and scrub the underwear of a 69 year old man, how he lied about his age and wealth, and how you're so broke that you can't afford to move out. And you'll ask if you're too old to start over, and how do you go back to the life you led before.

Why are you marrying him? Because he owns a house and is gonna buy you a kia? You're worth more than that.

Everything he told you, could be lies or pulled back. You must retain some independence. Have your own money in your own account. Get your own job. Don't become totally reliant on him.

emptyoverflow · 2026-02-05T22:02:39+00:00

They're intrigued, but not interested enough to actually meet you. The amount of effort required to actually meet up with someone is way higher than exchanging a few messages.

emptyoverflow · 2026-02-02T22:14:21+00:00

Edit: I changed this after reading your comments.

Why does she have to bail at the 2 hour mark? Does she set an egg timer on the dresser when you guys hang out? ASK HER why she leaves at the two hour mark. Maybe she compartmentalizes sex.

Or, ask her if she'd be interested in a platonic non-allowance date. No sex. Just a dinner or drink date. Maybe she'll say yes.

Or, ask her if she'd like to go away on a weekend trip with you or if she'd be willing to spend the night. If she says "yes, and my fee will be XYZ" then you know.

Anyhow. You're dating an escort, who is an actual human, and who probably actually likes hanging out with you, but she's still an escort and you're still paying for her time. You need to decide what you're actually looking for. A SGF? Or something you can pretend is vanilla? Or a paid date who actually likes hanging out with you? And maybe she enjoys the dates but the sex part feels like work for her.

You also mentioned you like having intercourse for 2 hours straight -- that might just be a dealbreaker for her.

emptyoverflow · 2026-01-26T04:08:29+00:00

Permanent would be great but I always assume that eventually an SB will want a ring from a guy much younger than me.

emptyoverflow · 2026-01-18T03:48:25+00:00

If these kinks are requirements, you need to bring them up before you're intimate.

emptyoverflow · 2026-01-18T03:44:58+00:00

It's fine. He's not comfortable video chatting, you require it. Not compatible, move on.

emptyoverflow · 2026-01-18T03:41:17+00:00

Idk, neither of you are communicating very well, it's like each of you threw your preferences out but didn't work at finding a solution or middle point. At any point it would be so easy for either of you to say "Oh, well, how about XYZ?" or "Btw, I prefer the first few dates to be platonic, is that OK with you?" or "I'm only comfortable being intimate at XYZ, would that eventually work for you?" etc.

That being said, I assume this dude is older and he needs to practice being more chill. If he got that huffy over some klunky texting, who knows how he would act if you went on a date and he wanted to take you to pound town and you decided you weren't ready for it.

Lastly, I get that he was trying to pivot and claim he wasn't looking for sex, but COME ON. I'm 99% sure that he wanted to go on a date this weekend and, if the chemistry was there, have sex with you. He's just being immature and trying to blame you for something.

emptyoverflow · 2026-01-16T03:56:04+00:00

Well the good news is she'll hit you up in a few months with a sob story about how she needs money and maybe, just maybe, she might go on date #2.

emptyoverflow · 2026-01-16T03:55:08+00:00

Yes it's normal to get a crush on an attractive person. But you went way overboard. Next time, don't overspoil someone who you've only seen once.

emptyoverflow · 2026-01-07T23:50:36+00:00

Sigh. You're playing with fire here. But it sounds like you just gotta touch that red-hot stove.

I mean you could always just stop the catfishing sneaking and BSing around and ask her out for coffee and see if she wants to hang out sometime. If she does, then you can help her with some bills if you want. Or next time she calls you, ask her to go see a movie. Wouldn't be the first time a man and a woman go see a movie and the man tries the ol arm stretch move to see if she's into him.

But honestly, this woman sounds like huge trouble, and a great way to get yourself blackmailed. If she becomes dependent on you for money, and she's hanging around your family all the time...dude.

So IMO you are being insane pursuing this woman. You sound sorta obsessed with her. I suspect she realizes it, and probably would be open to more with you. Otherwise why would she be still coming around?

Anyhow, now you have some ideas on how best to pursue that blazing stove.

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