Should I date him?

I’ve been online friends with a man for 10 years. I am a woman btw. He has been there for me through many things over the years like my divorce, family and pet deaths to name a few. The divorce was 5 years ago. He has always had romantic feelings for me. In the last couple of months, I’ve developed feelings for him as well. He lives about 4 hours away, but we’ve never met.

We’ve talked about maybe dating. I have some fears about it though. My biggest fear is that we meet and there’s no attraction there. It could very likely ruin the friendship and he is extremely important to me as a friend. I am able to talk to him about things I’m not with anybody else. I know some people feel that a friend you have online isn’t a “real” friend, but he is very very dear to me.

There are a few other things that concern me as well. We are both close to 40 but he is a virgin. I’ve seen pictures of him, he’s not a freak so it’s not that. He says he has had many opportunities but he just doesn’t want to have sex for the sake of having sex.

He has social anxiety which prevents him from getting and keeping jobs. He lives with his mom and helps home school his nephew. He has a car and doesn’t seem to be broke. His finances really aren’t any of my business so I’ve not asked any specific questions about them.

I’ve seen pictures of the inside of the house and there is just stuff everywhere. They aren’t hoarders, but man, there’s lots of stuff.
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Even without anything romantic, I love him. He’s my closest friend and there have been days when we stay up till the sun comes up, just talking. There is also a lot of talk about sex and we’ve come pretty close to cybering. We have plans to meet in a few months. I know that we could have a great time hanging out for a few days. But then what? Is this somebody I could build a future with? Probably not.

Anyway I’m just looking for other peoples opinions on this. It’s hard to keep perspective when you’re right in the middle of a situation.

I would go for it. 10 years is a long time for any relationship, even an internet relationship. I would advise you both to keep your expectations low. I don’t think finding out you are incompatible would ruin the friendship. If it is as strong a friendship as you indicate, it will persist.

(I’ve never met a man online, but did fall in love with an acquaintance over the internet during summer vacation, and was definitely worried about ‘‘ruining our friendship.’’ We’ve been together about 7 years now, married for three, very very happy I took that risk.)

Cautiously, I say yes. That’s a long friendship and it sounds like you two are good for each other. Life is short.

I have fallen in love with a man online and it’s the best thing that ever happened to me. (He’s making me dinner right now.) You learn people from the inside first and sometimes that’s perfect. <If everyone is honest–there are jerks out there.>

Without risk, there is no reward.

My current boyfriend started out as my best friend for several years before we got together. This has been the best relationship I’ve ever had and we are planning to get married.
I definitely think that a solid friendship is a great basis for a romance.

The clutter and the social anxiety probably both have a lot to do with his mom more than him. Finding someone who genuinely cares about you and is loyal through the hard times is a rare and precious thing in my view, and I think it’s worth giving someone like that a chance.

I do think that it is probably best not to build up the first meeting into some huge, make or break thing though. With how shy he is, it would probably be a huge mistake to go to the first meeting expecting instant fireworks and hot and heavy sex right away. Take it slow and don’t put a lot of pressure on things right away.
When my boyfriend and I first got together officially, I was very nervous about kissing him at first…but I did get over that. :wink:

Interesting. I really expected anyone who replied to tell me that I should not get involved romantically with him.

We are very good for each other and bring some happiness into two otherwise pretty lonely lives.

I also worry about hurting him. He’s not an overly emotional person but I know that he’s really hoping for this to work. And honestly, I can see me being the one to say that I’m not interested. I don’t think he would, he’s cared about me for too long.

No job? 40 year old virgin? Lives with his mom? “Social anxiety?” Family of hoarders? Fixated for 10 years on an cyber GF who he’s never met? Yeah, that sounds like a real winner.

I’d say go ahead and meet him in person, but don’t give him any expectation yet that you intend to take the relationship to any new level. If magic happens, it happens, but don’t go in expecting it.

It also sounds like you know deep down you aren’t really attracted to him in that way, and you say yourself you don’t think you’d have a future with him. I’d really advise keeping it at the friendship level on your first meeting. You could end up losing what you value about the relationship if you try to force it into something you aren’t really whole-heartedly into.

Be prepared for a full metal Romeo, by the way. This sounds like the kind of dude who’s liable to pull a ring on you if you aren’t careful. Be prepared for an “I’ve always loved you, marry me” speech, and have an answer ready.

You’re not responsible for his emotional health. Don’t do anything because you feel guilty. Only do it if you really want to do it with all your heart. No pity fucks. That will just make it worse for him if you ultimately decide you don’t want it to go any further.

That’s more of what I expected and for some reason it’s got me killing myself laughing.

I know that on one hand the whole thing is absurd. But on the other, there has to be something there if we can spend almost the entire weekend talking with each other. He just accepts me the way I am. There’s no pretense, we can just be ourselves. And after 10 years we know each other very well. I know he isn’t lying to me about anything because if he was, it certainly wouldn’t be to say he’s a 40 year old virgin who lives with his mom.

He’s never pushed anything on me either. He just quietly lets me take the friendship where I want it to go.

“He has social anxiety which prevents him from getting and keeping jobs.”

I don’t know what that means, but it doesn’t sound very good. I’d be worried about financial issues - sure he’s got a place to live, now, but are there siblings who are going to have a claim on ‘his’ house when the mother passes? Do they even own the place outright? Are you willing to take care of this guy, is what I’m saying basically.

Then again, you two might be a perfect match.

So, like the others, I say proceed with caution. Don’t let him think you are coming down there to sweep him off his feet. It’s just a meet and greet, as far as you are concernd. At least at this stage. If things happen, fine, but take it very slowly.

I’m not saying it’s not a rewarding friendship, but that doesn’t necessarily translate into romantic love.

It sounds to me that it could be very good, very bad, or in between. But I’d say that you should give it a shot. Just be prepared for things to go wrong.

I don’t know anything about anything and have no standing to give any advice, but, for what it’s worth, this is how I felt about it as well. (I’m piping up only so you don’t get a skewed response.)

Oh, hell no!

I think you really know the answer to that question, don’t you? From the way you phrased your original post, you already know.

But then, maybe you’re willing to take over his mommy’s role…

No, I really don’t know. My heart says we could be really good together. My mind says there is no together.

In that case, what others have said to you: take it slow, don’t have great expectations, continue on a friendly level for a while. Wishing you the best of luck, FloatyGimpy.

I’m in my early thirties and there’s no way I’d get involved with a virgin. At this stage of my life, I feel like I’m past all that. To me, it’s not so much the lack of sexual experience. It’s more that it means he’s almost certainly never been in a long-term serious relationship and that means he has no practice or experience in the day-to-day function of a relationship. I’m just not willing to to be the guinea pig he learns on. Your mileage may, of course, vary, but you’ve been married and divorced so you’re at least Intermediate level, probably Advanced in Romantic Relationships and this guy is Beginner. Are you comfortable stepping into the role of teacher? Personally, I’ve had my fill of that from my own early years of dating and it’s not something I want to revisit now.

This guy has a lot of red flags. You don’t need me to tell you what they are, you laid them out in your OP. If you’re willing to have a go and see what happens then good luck to you. You don’t seem to be going into it completely blind, at least you recognise his shortcomings. Meeting him face-to-face will help you work out if there is a future in this, and you should probably arrange that as soon as possible. It’s only a two hour drive for each of you to get together for coffee some place in the middle - why not do that some afternoon soon?

No.

One thing I learned from my internet dating experience (which ended up in my marriage of seven years come August 24th) is that meeting in person sooner rather than later is the best way to go. You just don’t know until you’re face-to-face. Yes, he does have a lot of red flags, but you might be just the right-shaped lid for his pot.

By the way, social anxiety is very treatable if he’s interested in getting better. If he’s more interested in using it as an excuse, you probably won’t have a future together.

(snipped, obviously)

I’ve never understood this reasoning. Why the heck does being in a “serious relationship” require me to have had sex? Just because I’m male and have testosterone? I’m not the only person who considers it a moral issue, and something I just won’t do.

Now, combine that with the social anxiety and “still living with his mom” part, and I understand your inference.

I always will prefer a virgin. Why the heck would I trust someone who has had sex before to remain faithful “till death does us part”? Either they did it with someone else they loved and thought they were going to be with for the rest of their life, but turned out to be wrong (and, thus, they might be wrong this time), or they don’t consider sex important enough to wait.