Should I date him?

Please do. Everybody should.

I think sometimes shy people get trapped in a self fulfilling prophecy.
They haven’t had enough experience with interactions to feel comfortable, but they can’t get any experience in interacting with people normally because people look down on them for being awkward and inexperienced and avoid them.

Not everyone gets a good chance in their youth to learn social skills for various reasons (probably in this case including a dysfunctional family atmosphere from how this sounds). Okay, so what? That doesn’t make him a bad person. That doesn’t mean that he has nothing to offer. Clearly he has some worthwhile ideas to share if he can maintain the interest of a penpal for 10 years.

If anything, I think overly extroverted people have more to be ashamed of than the introverted sort does. I can’t recall a time that I’ve ever been bothered by a person quietly keeping to himself, but I’ve been bothered by a person yammering on non-stop or blurting out something inappropriate.

I agree with a lot of what you said. He doesn’t have the experience to get the experience. I’m not looking to save him or change him. I just think that, even as a friend, it would be good for him to get out and do something fun. And I’d have fun too.

However I have to take issue with the penpal thing. A penpal is somebody to whom you write a letter, and maybe in a couple of months or so, you get a reply then maybe in a couple more months, you write back. Somebody you communicate with a few times a year.

We have spoken on the phone or online almost every day for 10 years. I’ve though long and hard about it and I have to conclude that he and I are friends. He knows me better than my own relatives.

I know that some people feel that you can’t be friends unless you’ve physically seen the person standing in front of you. This is not how I am approaching this specific situation.

But I do understand that some people feel differently.

A 40 year old virgin? Run don’t walk to the nearest delete button. That is all you need to know .

I’m with you on that. Virgin by choice or by obligation, whatever, but when you start expressing your ideas about sex not being needed to be part of a serious relationship and saving yourself for a mystical, magical connection… that’s messed up. It tells me you have some seriously wrong-headed ideas about sex.

A serious long-term non-sexual relationship is a friendship. It’s not even nearly the same thing as a serious long-term sexual relationship, no matter how much you pretend.

Red flag! Red flag! Red flag!

You know, just in case you missed it or something.

A balanced relationship is not based on pity.

Speaking as a 40-year old virgin, I would suggest that you not date this gentleman with the expectation of a long-term romantic relationship. And it’s nothing to do with his virginity or lack of romantic experience. He’s never had to work for a living. Social anxiety means that you won’t be going many places with him. Living with his parents all that time (I think we would all excuse him for having had to move back in with his parents if he’d lost his job) means that he’s never had much responsibility. Hoarding too - you’ll be forever picking up after him.

Dating him, however, would probably be the greatest gift you can give him, even though it may mean the end of your friendship. For whatever reason, this man hasn’t managed a romantic relationship before and having one with you will give him that experience. The next woman will undoubtedly thank you.

(For my own part, I can’t make people laugh. In person, I’m pleasant enough company, but I’m not good company. So romance has yet to blossom. As for sex, I was previously employed in a job where visiting a prostitute would have been a CLM. And now I can’t afford it. And I’m now accustomed to my own company anyway. But I’ve yet to give up hope.)

FloatyGimpy: All this time and you haven’t said one word about what he looks like. What does he look like? Do you find him physically attractive.

Regarding the “penpal” thing–I agree with you that penpal isn’t the right word to describe your relationship. The English language hasn’t caught up with the realities of the internet age. (Nor has it really caught up with the fact that people have long-term stable partners with which they live but to whom they’re not married.) We could really use some new words for the kinds of relationships that form over the internet.

Dio–I’m not a sig-using woman, but this one’s for you…

Gah! Didn’t work. It was there on preview…

ETA: Didn’t work again. I guess the hamsters don’t think you’re dead right.

Hmm. Sig test.

Hurm. Mine doesn’t work either. That’s probably a good thing. Mine is incredibly filthy.

Sure, I’ll agree with that, and additionally agree that relationships before my marriage weren’t mature and adult shudders just thinking about them. Though I hope you don’t think that people who are virgins until marriage necessarily think exactly like your hypothetical (for starters, this idea about being afraid to see someone naked or touch a booby… lemme just say, HA!), though I’m sure some do. It also works the other way: why introduce a level of physical intimacy unless the emotional/intellectual/commitment levels of intimacy are also there? And I think people can vary wildly in how they rate the various levels relative to each other and what is right for them, which is all that’s really being said by anyone in this particular thread. For me, being mature and adult also went along with a high level of commitment, whereas I understand that others don’t necessarily think that way.

Also, I agree that sex shouldn’t be regarded as a mystical, magical connection. (I don’t think anything, including marriage, should be, either. Ew.) Highly significant-- well, it’s possible to make babies from it, which I think is certainly highly amazingly cool, and worth a modicum of respect.

Anyway, to stop derailing, two things that occur to me because of Green Bean’s perceptive posts: 1) you may feel differently about how attractive he is when you actually meet him… phone conversations are way better than the internet for getting the feel of someone, but they won’t answer questions like “Does he have strange nervous tics? Do you agree on what is acceptable interpersonal space?” 2) I can also see Green Bean’s point about it being dangerous for him for you to meet him. For most of us it’s good to have a certain amount of relationship heartbreak; it helps us grow. For him, with his longstanding people issues, I’m worried it might just crush him – but you know him better than I do.

I think so, too. I also think there’s a good chance that I’m the only woman who will come along. He and I have talked about what it could mean if we did date and I’ve said to him that it could ruin the friendship. He says that for his part, if it didn’t work, he would still want to be friends. This might be the only chance he has to have a woman, who really cares about him, wrap her arms around him for a while.

As for his looks, he looks fine. He’s a normal, average looking guy and looks are a bit down on my list of important qualities.

To expand a little on his job/living situation, he did get a job and move out when he was young. He did have trouble keeping them though because he had to deal with people. When he was out of work, his dad died, so he moved back in with his mom and has been there for about 6 years now. He’s had one job since then, just for a short while. His mom worked and his sister is a single mom of two young boys, so he took care of them while she worked.

Nobody’s pointed out yet that these two statements are not mutually compatible.

If he hasn’t gotten to the point of holding hands with someone, he has not actually had an opportunity to have sex with them. Unless by “having an opportunity” he means being solicited by prostitutes.

Maybe he’s had the opportunity to hold hands, but turned it down because it was too intimate for him.

Given this, I think it is possible and probable that he is reading this thread!

It’s not like you have to marry him. So yes, date him if you want to. Nothing is set in stone.

Some somewhat random thoughts/questions, bouncing back and forth between dating and considering what would happen in a long-term relationship:

  • He has put you on a pedestal, and that’s never a comfortable place to be. You inevitably fall off at some point, and that’s no fun for either of you.

  • You’re imagining this trip to involve going out, sight-seeing, having fun. If he has social anxieties, is he going to be able to do that? Or is he imagining a weekend of hanging out at the hotel, just the two of you? Are you ok with that?

  • Long term, if you did date, how would you deal with the social anxiety? Are you someone who likes to go out with friends, go out to the movies, have friends over for dinner? Would he be able to do that?

  • Does he have any outside activities? If not, that’s a huge responsibility on you to be his only source of entertainment. What happens when you’ve had a bad day and need some space? What’s he going to do? What do you talk about over the dinner table if he hasn’t gone out and actually done anything? If you’re doing all the talking, and he’s doing all the listening, he’s your therapist, not your boyfriend.

  • If you are more outgoing/active, would he start to resent that over time? Would he expect you to come home to chat online/on the phone every night when you want to be able to go out with friends/participate in outside activities?

Wow.

For once, I’m at a loss for words.

What’s a CLM?

Career limiting move. Were you in the priesthood or something, Quartz? :wink: