I do chatbots focused on interesting conversations. Not specifically to solve this; it's just that I find most conversations dull and I'm the kind of person who would marathon Sorkin/Tarantino just to listen to people talk.

Would you be interested in an open ended first date sim? It could be voice so you get used to voice; one issue I have is I can type well but the brain circuits don't trigger the same way when talking.

Possibly start with an interested date at lower difficulty - someone who asks you the questions and coaches you into interesting answers. Then ramps up to shy/unfriendly where you have to work to get them engaged.

This is definitely cyberpunk dystopian response.

Lonely? Why not talk to machines?

Grim.

Talking is a skill. Skills are improved with usage and practice. Not everyone wants to practice on another human. Honestly, it's a bit of a jerk move to date people to practice dating someone better.

When people say they're unattractive, often it's not because they're ugly. Ugly is a disadvantage, but not the biggest one.

For both men and women, it's usually because they lack confidence. Or they're boring. Or sleazy. If you're getting into a first date and not a second, you're likely attractive enough on the 'resume', just messing up on the actual date. You might be saying something wrong. You might be delivering a good joke the wrong way. Sometimes it's just saying things in the wrong order.

The longer they go without some form of success, the less confident they become.

I thought the diagnosis was fairly clear; sorry for jumping straight to pitching a cure. This is a good example of saying things in the wrong order.

> I thought the diagnosis was fairly clear; sorry for jumping straight to pitching a cure. This is a good example of saying things in the wrong order.

That you think LLMs are the cure to loneliness misses what a "cure" even looks like here. OP clearly writes well enough to get first dates - the issue isn't conversational content but likely body language, energy, presence, the thousand micro-signals that happen below conscious awareness. You can't chatbot your way into better posture or more relaxed eye contact.

This is classic LLM wrapper syndrome. Someone has a hammer (conversational AI) so every problem looks like a nail (conversation optimization). But the actual failure mode here probably happens in the first thirty seconds of meeting, before anyone's even said anything substantive.

Op would probably benefit more from something social like improv classes (physical presence, spontaneity), dance lessons (body awareness, comfort with proximity), or honestly just hanging out in social spaces doing things they actually enjoy rather than performing "date behaviors." The energy of someone genuinely engaged in something they love is magnetic in ways that no amount of conversation optimization can replicate.

I just don't believe that "practice talking to a computer" will ever be a sufficient platform to teach people how to be genuinely charming, let alone charmingly genuine.

I was thinking like this, but after being married before I'm not even sure I want to date. I have friends, hobbies, kids in school to manage. Not really feeling the dating scene right now. I do enjoy talking to and meeting new people but often do this as part of hobbies or groups I've joined rather than in the context of "dating".

Are you looking because you're lonely, bored or just because that's what you think is expected?

Maybe ask them after without coming across as desperate? Something like:

"Thanks for being honest and I wish you the best with your search.

If you have a moment, would you be able to give me a few suggestions on how I could improve? Is it something obvious I can work on but just not aware of? Like my breath stinks? Or clothes don't fit properly? Or I come off as rude or closed off? Of course, no pressure to answer. Just trying to figure out how I can improve myself. Thank you."

I do give feedback when they ask for it, but it ends up with a foot on the door. "But I'm not like that! But I can change! But your breath stinks too!!"

Yes that's where you gotta embrace whatever feedback they give even if you think it doesn't apply to you. Thank them for taking the time to respond and move on without arguing back.

I would lead with making it very clear that you don't ask this to make it work with this person, but to make it work with the next.

This is fantastic!

Be ready to hear things you may not like but hopefully it gives you something to work and improve on. Regardless of whether they say something offensive or rude, thank them for taking the time to respond and don't try to argue with them. Wishing you the best.

Things will get easier women after 40 are less selective.

He prolly wants someone younger, hence the difficulty. :)

Have you tried visiting different countries and try to date there? Depending on the country it can make a huge difference

> complex situations where you've tried multiple approaches but nothing quite clicks

What are the multiple approaches you've tried?

You can pay $$$ to solve it. They say it's the world's oldest profession (or p2p business if you prefer).

You don't feel the spark, or they don't?

Sample size issue?

They. Probably a "someone better is one swipe away" (?) issue.

How do you know?