u/Vast-Signal-7816

To cut a brutally long story short, I'm 29F and very inexperienced in dating. Culturally sheltered by my parents, didn't try dating until after college, only been in one LTR that ended 2 years ago.

Tried dipping my toes back into the dating pool this year. It's been... rough. I kept rejecting/turning down dates out of nerves. Only so many guys where I live (rural area), so I've been burning bridges left and right.

Finally matched with a guy a while back. Great convo via text/phone. Finally said screw it and went on a casual coffee date. It... was not great. I was super shy/quiet/awkward, but was shocked when he asked to see me again. Second time around was better, but still not great.

Understandably, he's not really interested and gave me the whole 'not ready to date' spiel. However, he said he'd still be up for drinks/casual/etc. and still occasionally keeps in contact.

He flaked at meeting up last weekend, but seemed adamant about this coming weekend. Even after I gave a polite 'if you're not feeling it.. no worries...' he still wants to meet up?

Guess I have a few questions here. Okay to meet up with him just for the experience? Is this probably a pity date? Why hang out with a girl you seemingly weren't interested in?

Just very confused, as for various reasons, he doesn't seem to be looking for a hookup...

Please be kind. I know I should move on from this, but I live in a rural area for work, with no friends/family close by. Just a lonely person :(

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There's a guy I'm quite interested in. First met on an app 2 months ago. Amazing conversation via text/phone. Could easily chat for 4+ hours. Met up twice. I had a good time, he said he did (could easily be a formality). However, I can tell we're both somewhat introverted and a bit awkward. Or, at least, he's not one of the 'smooth players' I've gone out with.

Anyways. I know he's not interested. Our communication has dropped like a rock.

However.

I really don't understand why he keeps entertaining me whenever I do reach out. He always responds pretty quickly to my texts. When I bring up hanging out, or grabbing drinks, he's always keen. It's never a vague 'yeah, maybe' it's a 'Looks fun! Sounds great! Next weekend!' etc. Then... he flakes. But then kicks the can down to the following weekend?

I just... I know I need to give this up. Easier said than done, though.

Also tried to give him an 'out' a few days ago, by saying that if he wasn't up for hanging out, I'd absolutely understand, no worries, etc. but he quickly replied that no, 'it's ok!' 'you're good!' 'next weekend!'

Just very confused. Assuming I'm a backup option? He's just bored? Bad at rejection? All of the above? lol

Single woman in my early 30s, living near California, looking for things to do. Moved here a while back, and I'm only here another year.

Very fortunate to have made friends with my neighbors, but they are all twice my age and retired.

Any pickleball, trivia, hiking/running clubs etc.?

Up for anything that is welcoming to someone solo!

Please feel free to share any ideas or insights. Unfortunately don't have the time (or energy) to be driving up to DC for things.

Thanks!

Edit: Does anyone have any specific info on trivia? Finding lots on Facebook about running clubs/pickleball, but not as much about trivia. Thanks!

I matched with a guy on an app about 6 weeks ago. We are both transplants to the rural area where we live and have a ton in common. Could easily talk/text for 5-6 hours. Meeting up was interesting, though. Can tell we were both nervous, awkward, and shy. He asked to hang out again, we did, and it felt a lot more natural the second time around.

We both mutually stopped texting as much, though. I finally reached out and had a pretty deep conversation with him. I've got personal stuff to work through regarding work and family. He likewise told me he realized he wasn't ready to start dating again. Which, I'd otherwise take as a polite rejection, but numerous signs tell me he actually meant that. Deleted his app, likely has some unresolved PTSD from work, has been divorced, and had a broken engagement a year ago.

He did seem very up for/eager to meet up for drinks again sometime. Not having many friends here myself, I'd love the opportunity. He flaked once (after suggesting the time/place), and our plans just never materialized.

tl;dr - He's part of a group that does trivia nights at a local brewery. We live in a rural area, so there's not much else to do. It's something that I've always wanted to do, but never got around to. I'd never think of asking him if I could tag along with him. However, would it be appropriate to ask if they're welcoming to newcomers, or ask if he knows of any other trivia spots?

Trying to put myself out there, but finding it extremely difficult at every turn 😞

Important background info, I'm 28 and moved to a rural area for work 2 years ago. Don't have family here, only a few friends. Dating/making friends has been difficult for me, as I have very little in common with most people here.

A month ago, I matched with a guy on an app and.. damn. We're both from the same area, so this doesn't surprise me, but we have a ton in common. Could talk/text for hours. First time we met up was admittedly awkward. Think we were both a bit nervous, and I'm naturally a bit shy at first. He asked to hang out again, which we did. The second meet-up was much better.

Anyways. His communication dropped quickly after. We had a long convo about life and whatnot. He shared that he's not emotionally in a place to date after a bad breakup (failed engagement), which I actually believe, because he deleted his dating app profile.

However, he still seemed keen on hanging out sometime. Once, even suggesting the time/place. He did flake twice, though.

tl;dr - Question is: okay to keep texting him infrequently (maybe 1-2x a month) to see if he'd be down to grab drinks or whatever that weekend?

I really don't care if this makes me look desperate or whatever. I don't have a ton of friends here. He's also responded quite positively every time I've done so. Personally, if I wasn't interested, I'd either not respond or give a vague 'yeah maybe sometime'

I know men aren't a monolith, but okay to keep checking in/reaching out to a guy as long as his response is positive?

Edit: sorry everyone, I live on the west coast (US), so update will take a while!

I have zero shame anymore. I'm nearly 30 and just don't give a fuck. Younger me would probably be shocked and ashamed.

Went on a few dates with a guy a month ago. He basically said he's still not over his ex (may be true, may be a polite rejection, whatever)

Anyways, tonight I'm just gonna text him and basically say that if he's ever up for some fun to hit me up lmao

Mostly expecting him to ignore it, but meh. Again, don't feel like I can lose much here lol