Struggling with pacing

TL;DR: met young woman on dating app. Her profile said no hookups. After a day of chatting, she steered the convo in a sexual direction. I was down with it so I reciprocated the vibe. It went a little too well and she hit me with “we should hang out.” I felt intimidated bc of external factors and fumbled. She stopped responding. Now I am bummed.

Asking about: how do I navigate the pacing of modern dating without screwing myself over?

Ok so long story:

My (29M) profile clearly states “I’m mostly just looking for someone to chat with but I might be down to get together at some point if we hit it off.”

I have that in my profile because I find this whole process intimidating; I’m quite shy in some ways. The only successes I’ve had have come after becoming friends with someone first. Otherwise I feel rather uncomfortable/conflicted.

I matched with this young woman (20F) the day before yesterday. On her profile she had something about not wanting a hookup, which I found encouraging. I got her number and we texted back and forth a bit and had some decent convo.

After a day, she directed the convo in a sexual manner and I reciprocated. I do enjoy flirting and sexual convo despite my shyness, but I always feel conflicted when this happens… on one level I’m very down, but I also have some baggage from my upbringing that stirs up some unpleasant emotions (I came from a very strict household with a lot of screaming about these subjects). I feel these emotions are very unattractive so I try to hide them.

Anyway, her and I were talking about sex, and it was going well. She brought up a certain hot-button kink of mine and it turned out she was into it too. With that subject, I’m very into it so I tend to be less inhibited. Convo got pretty steamy.

She responded very positively but then paused to preface that she wasn’t looking for a one-time thing. I said that was good because I’m not either. Then she just flat-out said “we should hang out.” I think she had been dropping hints (“play me some music sometime”, “I’d love to see your place”, etc.), but I couldn’t really beat around the bush anymore with her saying it so overtly. Basically I got the sense she wanted me to invite her over asap.

Once she said that, the usual inhibitions came flooding back and I got intimidated. It’s kinda like a feeling of having the wind knocked out of you and looking around as you try to take a breath, but one doesn’t come.

I tried to save face and suggest we go for a walk or something. She said she was cool with that, she just “wanted to meet me”, but I sensed the vibe had changed, like suddenly she was turned off by my lack of confidence. She stopped responding soon after and it’s been a day now. I felt embarrassed so I deleted her number. I’m just calling it a loss.

Now I feel foolish and disheartened. This has happened in various forms probably a few dozen times now over the years.

I feel ashamed about the patience I need to be shown in order to not clam up like this. I feel like it’s unattractive to explain it, but when I don’t, stuff like this happens, and I get disheartened.

I’ve only been with women who I was friends with first. I’m embarrassed to say that number is unusually low for my age; I don’t have a lot of experience. I try not to beat myself up about it but it gets me down. Many missed opportunities like this.

I feel so mixed up. I would really like to act on my desires, especially in situations like this where I share a complete favorite kink with someone… but I just hit a wall when it comes to meeting up so soon. Like, I want to, but even if she’s initiating things, I need a lot of assurance that it’s okay and welcome. Otherwise I kinda shut down, and then I beat myself up like this.

It’s not just that I don’t have sexual confidence, it’s that I feel like I’m not allowed to have it bc my upbringing is so deeply engrained. In the household I grew up in, being confident about sex was treated like being confident about walking on people’s fingers. That sense of shame and trepidation still runs very deep.

In the past, it’s literally taken women like… straight up inviting themselves over and asking me to have sex for me to feel assured enough to go through with it. Once that ice is broken it’s been good! But that amount of patience is kinda rare, I’m finding; seems like women I talk to are much more secure about this stuff.

I would love to be able to be free like the situation called for, but I’m just not able to muster the courage. I’m lonely and unfulfilled and I feel like it’s my fault for chickening out. I feel so dumb for screwing myself out of experiences I want to have, time and time again.

Idk. Thanks for reading. Just welcoming some input.

Just to mention, I have gone to several therapists about this. The advice they gave me didn’t seem to go over well (I think it came across as really un-sexy). I kind of just found myself going in circles session after session and sometimes I would leave feeling worse than when I went in, which never translated to a better dating life.

Submitted June 01, 2022 at 12:15AM

TL;DR: met young woman on dating app. Her profile said no hookups. After a day of chatting, she steered the convo in a sexual direction. I was down with it so I reciprocated the vibe. It went a little too well and she hit me with “we should hang out.” I felt intimidated bc of external factors and fumbled. She stopped responding. Now I am bummed.Asking about: how do I navigate the pacing of modern dating without screwing myself over?Ok so long story:My (29M) profile clearly states “I’m mostly just looking for someone to chat with but I might be down to get together at some point if we hit it off.”I have that in my profile because I find this whole process intimidating; I’m quite shy in some ways. The only successes I’ve had have come after becoming friends with someone first. Otherwise I feel rather uncomfortable/conflicted.I matched with this young woman (20F) the day before yesterday. On her profile she had something about not wanting a hookup, which I found encouraging. I got her number and we texted back and forth a bit and had some decent convo.After a day, she directed the convo in a sexual manner and I reciprocated. I do enjoy flirting and sexual convo despite my shyness, but I always feel conflicted when this happens… on one level I’m very down, but I also have some baggage from my upbringing that stirs up some unpleasant emotions (I came from a very strict household with a lot of screaming about these subjects). I feel these emotions are very unattractive so I try to hide them.Anyway, her and I were talking about sex, and it was going well. She brought up a certain hot-button kink of mine and it turned out she was into it too. With that subject, I’m very into it so I tend to be less inhibited. Convo got pretty steamy.She responded very positively but then paused to preface that she wasn’t looking for a one-time thing. I said that was good because I’m not either. Then she just flat-out said “we should hang out.” I think she had been dropping hints (“play me some music sometime”, “I’d love to see your place”, etc.), but I couldn’t really beat around the bush anymore with her saying it so overtly. Basically I got the sense she wanted me to invite her over asap.Once she said that, the usual inhibitions came flooding back and I got intimidated. It’s kinda like a feeling of having the wind knocked out of you and looking around as you try to take a breath, but one doesn’t come.I tried to save face and suggest we go for a walk or something. She said she was cool with that, she just “wanted to meet me”, but I sensed the vibe had changed, like suddenly she was turned off by my lack of confidence. She stopped responding soon after and it’s been a day now. I felt embarrassed so I deleted her number. I’m just calling it a loss.Now I feel foolish and disheartened. This has happened in various forms probably a few dozen times now over the years.I feel ashamed about the patience I need to be shown in order to not clam up like this. I feel like it’s unattractive to explain it, but when I don’t, stuff like this happens, and I get disheartened.I’ve only been with women who I was friends with first. I’m embarrassed to say that number is unusually low for my age; I don’t have a lot of experience. I try not to beat myself up about it but it gets me down. Many missed opportunities like this.I feel so mixed up. I would really like to act on my desires, especially in situations like this where I share a complete favorite kink with someone… but I just hit a wall when it comes to meeting up so soon. Like, I want to, but even if she’s initiating things, I need a lot of assurance that it’s okay and welcome. Otherwise I kinda shut down, and then I beat myself up like this.It’s not just that I don’t have sexual confidence, it’s that I feel like I’m not allowed to have it bc my upbringing is so deeply engrained. In the household I grew up in, being confident about sex was treated like being confident about walking on people’s fingers. That sense of shame and trepidation still runs very deep.In the past, it’s literally taken women like… straight up inviting themselves over and asking me to have sex for me to feel assured enough to go through with it. Once that ice is broken it’s been good! But that amount of patience is kinda rare, I’m finding; seems like women I talk to are much more secure about this stuff.I would love to be able to be free like the situation called for, but I’m just not able to muster the courage. I’m lonely and unfulfilled and I feel like it’s my fault for chickening out. I feel so dumb for screwing myself out of experiences I want to have, time and time again.Idk. Thanks for reading. Just welcoming some input.Just to mention, I have gone to several therapists about this. The advice they gave me didn’t seem to go over well (I think it came across as really un-sexy). I kind of just found myself going in circles session after session and sometimes I would leave feeling worse than when I went in, which never translated to a better dating life.