I think that this guy has massive issues surrounding sex, which is why he was too nervous to perform and why he can't finish with you. I suspect the issues can be worked out either with time/patience and/or with the help of a professional. It's up to you whether you want to work through them with him, but I don't think that there's anything there that can't be overcome if he is willing to work on it.

I am going to bet on too much porn and masturbation. He has "taught" himself to only be able to orgasm one way. He also probably started watching weirder and weirder porn.

I would tell him to try stopping porn and masturbation altogether and see what happens.

If he can actually get to the point of truly being "into" sex with you.... it's also very likely he will be more likely to bond and want a real relationship.

For what it's worth, I have been in two relationships with guys with similar "issues" and stopping (or really cutting down) on masturbation and porn changed everything (for the better). He will likely be a little sexually frustrated temporarily but the results will be worth it.

Anonymous wrote:

Anonymous wrote:Asking how you know if you love someone may be his shy, awkward way of telling you he’s heading in that direction and trying to diss out your feelings.

This is what I thought! But he keeps saying he does not want a serious relationship and I told him jokingly “Oh I have a crush on you” and he was like “That’s not good, this can’t get serious.” But I’ve been with men who don’t want a serious relationship in a “I don’t like commitment I just want to have sex with everything” kind of way and this doesn’t ring true to that experience. So idk if this guy is truly not into me and good at playing clueless or if he has serious attachment issues. Either way I cant stick around, but the sex is good now.

Also worth noting I made a point of telling him he doesn’t talk about his feelings a lot and he was like “I guess if I loved you I would” which seems very blame-y for someone who has gone three decades without a relationship. Suffice to say I know what I need to do, am just curious about wtf this guy’s issues are.

Anonymous wrote:Asking how you know if you love someone may be his shy, awkward way of telling you he’s heading in that direction and trying to diss out your feelings.

This is what I thought! But he keeps saying he does not want a serious relationship and I told him jokingly “Oh I have a crush on you” and he was like “That’s not good, this can’t get serious.” But I’ve been with men who don’t want a serious relationship in a “I don’t like commitment I just want to have sex with everything” kind of way and this doesn’t ring true to that experience. So idk if this guy is truly not into me and good at playing clueless or if he has serious attachment issues. Either way I cant stick around, but the sex is good now.

^ ugh “suss out”

Asking how you know if you love someone may be his shy, awkward way of telling you he’s heading in that direction and trying to diss out your feelings.

Definitely something to think about, but I think I would be inclined to talk about it and give him another chance if he’s otherwise a nice guy, and someone yiu enjoy so ending time with and are attracted to him.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:I posted this late last night but I guess it got deleted? Wtf, I didn’t think it was that graphic. Anyway I will try to keep it short. What kind of intimacy issue is it when a guy hasn’t had sex for eight years because he’s scared to ask women to have sex?

What's the context? Do you mean for one-night stands or in a long-term relationship or casual FWB?

We’ve been going out for a couple months and just recently had sex for the first time. He could not get it up and I asked about it. I do not think a relationship is on the table at this point. He has never had a girlfriend and asked me how you can tell if you love someone so I think he may be a lil messed up. Late 20s/early 30s.

Performance anxiety?
Autism spectrum?
Schizoid personality?

Yes, I think he may be on the spectrum. He is very sweet but very awkward and has no concept of how to interact romantically. He did seem to pick up sex quickly but the fact that he doesn’t know how to tell if he loves someone combined with the fact that he didn’t try to have sex for eight years because he’s scared of making women think he enjoys sex was a red flag to me. It just seems like a huge intimacy issue or disorder.

Porn?

And, of course, it is a red flag. But it doesn't have to be that way if you are open and accepting. But him not being able to get it up is a concern with this, too.

I asked about porn/masturbating and his response was basically “I haven’t had sex for eight years so yeah obviously.” He only couldn’t get it up the first couple times. Now he can and it’s fine. Still has difficulty staying hard the entire time and waits for me to finish, then goes to masturbate. It’s weird but it’s fine on my end so I’ve stuck around a few times. But as I said, I don’t even know his interest in a relationship. He uses very old fashioned, flowery language to describe me and sex with me and then is like “Hey I have a question how can you tell if you love someone? Do we have to have a ton of stuff in common to date each other?” Lol wtf?

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:I posted this late last night but I guess it got deleted? Wtf, I didn’t think it was that graphic. Anyway I will try to keep it short. What kind of intimacy issue is it when a guy hasn’t had sex for eight years because he’s scared to ask women to have sex?

What's the context? Do you mean for one-night stands or in a long-term relationship or casual FWB?

We’ve been going out for a couple months and just recently had sex for the first time. He could not get it up and I asked about it. I do not think a relationship is on the table at this point. He has never had a girlfriend and asked me how you can tell if you love someone so I think he may be a lil messed up. Late 20s/early 30s.

Performance anxiety?
Autism spectrum?
Schizoid personality?

Yes, I think he may be on the spectrum. He is very sweet but very awkward and has no concept of how to interact romantically. He did seem to pick up sex quickly but the fact that he doesn’t know how to tell if he loves someone combined with the fact that he didn’t try to have sex for eight years because he’s scared of making women think he enjoys sex was a red flag to me. It just seems like a huge intimacy issue or disorder.

Porn?

And, of course, it is a red flag. But it doesn't have to be that way if you are open and accepting. But him not being able to get it up is a concern with this, too.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:I posted this late last night but I guess it got deleted? Wtf, I didn’t think it was that graphic. Anyway I will try to keep it short. What kind of intimacy issue is it when a guy hasn’t had sex for eight years because he’s scared to ask women to have sex?

What's the context? Do you mean for one-night stands or in a long-term relationship or casual FWB?

We’ve been going out for a couple months and just recently had sex for the first time. He could not get it up and I asked about it. I do not think a relationship is on the table at this point. He has never had a girlfriend and asked me how you can tell if you love someone so I think he may be a lil messed up. Late 20s/early 30s.

Performance anxiety?
Autism spectrum?
Schizoid personality?

Yes, I think he may be on the spectrum. He is very sweet but very awkward and has no concept of how to interact romantically. He did seem to pick up sex quickly but the fact that he doesn’t know how to tell if he loves someone combined with the fact that he didn’t try to have sex for eight years because he’s scared of making women think he enjoys sex was a red flag to me. It just seems like a huge intimacy issue or disorder.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:I posted this late last night but I guess it got deleted? Wtf, I didn’t think it was that graphic. Anyway I will try to keep it short. What kind of intimacy issue is it when a guy hasn’t had sex for eight years because he’s scared to ask women to have sex?

What's the context? Do you mean for one-night stands or in a long-term relationship or casual FWB?

We’ve been going out for a couple months and just recently had sex for the first time. He could not get it up and I asked about it. I do not think a relationship is on the table at this point. He has never had a girlfriend and asked me how you can tell if you love someone so I think he may be a lil messed up. Late 20s/early 30s.

Performance anxiety?
Autism spectrum?
Schizoid personality?

Is he dating? Does he have other issues he's been dealing with (e.g. sexual or physical abuse). Is he married? Is he older, younger?

Anonymous wrote:

Anonymous wrote:I posted this late last night but I guess it got deleted? Wtf, I didn’t think it was that graphic. Anyway I will try to keep it short. What kind of intimacy issue is it when a guy hasn’t had sex for eight years because he’s scared to ask women to have sex?

What's the context? Do you mean for one-night stands or in a long-term relationship or casual FWB?

We’ve been going out for a couple months and just recently had sex for the first time. He could not get it up and I asked about it. I do not think a relationship is on the table at this point. He has never had a girlfriend and asked me how you can tell if you love someone so I think he may be a lil messed up. Late 20s/early 30s.

Anonymous wrote:I posted this late last night but I guess it got deleted? Wtf, I didn’t think it was that graphic. Anyway I will try to keep it short. What kind of intimacy issue is it when a guy hasn’t had sex for eight years because he’s scared to ask women to have sex?

What's the context? Do you mean for one-night stands or in a long-term relationship or casual FWB?

I posted this late last night but I guess it got deleted? Wtf, I didn’t think it was that graphic. Anyway I will try to keep it short. What kind of intimacy issue is it when a guy hasn’t had sex for eight years because he’s scared to ask women to have sex?