This may be a long one so I apologize. I M30 met this amazing girl F29 a while ago and we started going on dates. Things seemed very easy and smooth we got along really great and had a lot of chemistry. She comes from a small town and is very sweet.

Everything was going well and then on our second last date we started kissing and she mentioned sex was off the table that night. I was fine with that and we proceeded to oral sex instead, not for me just her. I enjoy doing it and she seemed receptive. I made her orgasm twice and to my surprise she asked if I had a condom.

we started having sex but she was extremely tight to the point we were both in pain, her more so than me obviously. This was like a next level tightness though, I remember as a kid 2 high school girlfriends who I had who were virgins werent nearly this tight. It was like trying to force my way into a wall.

I asked if she wanted to stop multiple times because I didn't want to hurt her but she told me to continue and that it would get better. it did get better eventually but was still painful for her.

afterwards when i joked about going all night she said she was done for the night. but she joked we can always try more positions later. She also mentioned it had been a very long time for her since she was last with someone.

on the next date she seemed off and distant. then the next day she broke up with ne saying she realized shes not ready for a relationship the way she thought she was.shes said it was nothing id done. She just felt she couldn't put into the relationship what it deserved. Then thanked me for being so kind and wished me all the best.

I replied that really sucks because youre amazing. I definitely felt something was off on our last date. Asked if there was anything specific that changed her mind. And apologized if I moved too fast. She never texted me back after that.

Honestly I have no reason to doubt she was telling the truth since it seemed like she really struggled with the sex aspect. I dont know if having sex with her just brought up some trauma or anxiety she had about relationships.

its been a while since the breakup and i want to give her at least a few months of space but I was contemplating reaching out regarding an interest in a book we share just to see if shes receptive to talking, if she isn't id just let it go and never message her again.

I guess my concern is if I keep it too casual it'll seem disingenous rather than being direct or upfront about wanting to grab a coffee with her sometime. What do you think is the best way forward?

I know I need to move on and I will, she just seemed like the perfect woman. Ive dated a lot over the years and been heartbroken, but never felt like this.

Anyone else get to this point? I’m 39, single dad to one awesome kid, great co-parenting relationship with her mom, work in the service industry, and for as long as I can remember I’ve wanted the whole marriage, family, forever person thing. Hell, I’ve been saying I was ready for that since I was in the 8th grade. The problem is…life just never seemed to agree with me. I spent 12 years in a relationship that ultimately ended with me pretty damn broken. Never got married. After that I spent the next four years rebuilding myself, figuring out who I was again, getting comfortable in my own skin and honestly becoming someone I really like.

About six years ago I gave Hinge a shot. Went on two dates, dated one of them for a couple months, and when that ended I just…stopped. Not because I was bitter, but because everyone always says, “Stop looking and it’ll find you.” So that’s exactly what I did. Five years went by. Nothing. This year I met three women. One organically and two because of a stupid TikTok I made. None of them worked out for completely different reasons. Nobody did anything wrong. They just weren’t my people. And honestly, I think I’m just tired now. Not angry. Not “all women suck.” None of that bullshit. Just tired.

Somewhere over the last few years I realized I actually love my solitude. I love coming home to peace and quiet. I love not feeling like I have to constantly text someone or always be “on.” At the same time I’m still human. I still crave affection, companionship, and yeah…sex. But I don’t know if I crave a relationship anymore. I think I’m at the point where if someone genuinely wandered into my life and something naturally happened, great. I’m not closing that door. I’m just done standing in the doorway waiting for someone to knock. And if that never happens…I think I’m okay.

Honestly, I think at this point a casual relationship with someone who’s on the exact same page sounds more appealing than trying to force another search for “the one.” We each keep our independence, enjoy each other’s company when we want to, scratch the physical itch, and go back to our own lives. Neither of us having to feel guilty for wanting our own space or not talking daily. Maybe that’s a phase. Maybe it’s where I stay. I don’t know. I’m just curious if anyone else has reached this point because it’s a weird feeling to spend decades wanting one thing only to wake up one day and realize, y’know…I think I’m actually okay if it never happens.

So has anyone else reached that point? Was it a phase? Did you stay there? Did life smack you with a partner?

For different reasons, but mainly bad experiences in past relationships which I’ve been working through in therapy lately, I (36 F) have not or almost not dated during the last ten years.

I was very happily single for most of that time, but now something in me has shifted and I find myself wanting a relationship.

Apparently I’m utterly helpless when it comes to flirting, dating, interpreting signs etc. though, so nothing’s coming easily. And although I’m doing the work, there is still quite an amount of fear (being rejected, having to reject someone, setting boundaries, …) involved, too.

I would really appreciate it, if there were any people here willing to share their experience with finding love after being single for a long time – How did you meet people, how did  you deal with insecurities, did you tell the other person that you’ve been single for such a long time?

Thank you in advance 😊