My worry is losing the friendship. Eh on the virgin and living with mum part. The no job part, no hand-holding and dehabilitating social anxiety is a little more worrying. But do you really want to throw away a friendship which clearly means a lot to you for a sexual relationship which you don’t seem hugely enthusiastic about?
Not quite: I was subject to security clearances. Lose those and lose the job.
Maybe you could have found a prostitute with the same clearance. 
He seems pretty excited about the plans. We’re going to go to see 2012, go to the omnimax and the aquarium, the zoo if the weather permits.
I’m not an overly social person myself. I get my socializing at work. He has never expressed even the slightest dismay if I’ve been busy and not been online for a day or two. I think that if he had any sort of those qualities, he’d have shown some of them over the last 10 years. The only thing he ever bugged me about was smoking and even that was sort of a joking “So, when are you going to quit smoking”. I did quit a year and a half ago, not because of anything he said, I just didn’t want to do it anymore.
He’s had some opportunities for sex while at the bar or a pub. Years ago he would go out to the pub on the weekends and sometimes a woman would come and talk to him, making it pretty obvious that she was wanting to go back to her place or something. He just didn’t want to go with some stranger and have sex. Eventually they stopped asking. I think there were a couple of times he was interested in someone but didn’t have the courage to go and say anything.
The more I’ve thought about it, the more I think it is a good idea to at least meet.
It’s not all about me wanting to do something nice for him. I genuinely care about and enjoy him and I think it would be fun for me as well.
This thread has evolved strangely.
In the beginning, it seems like you’re painting him as this most pathetic loser with no future and no present, no job, zero social life, zero sexual experience, and zero prospects.
You even said yourself that you don’t see a future in it.
But when people agree with the prospect, pointing out the importance of what you said yourself, you seem to be strongly defending him. Like, oh, he doesn’t have a job but he did have jobs before, and he moved out once, and he used to get offered sex at bars all the time, etc. etc.
That’s not really the way you portrayed him at the beginning of the thread, so I’m wondering if you were being disingenuous then or now.
She’s being disingenuous now. We’ve spoiled her fantasy. She’s trying to reclaim it.
If you’ve still got the edit window available to you: You’ve accidentally put “Originally posted by FloatyGimpy” instead of “ladyfoxfyre”.
If I ever portrayed him as a pathetic loser, that certainly was never ever my intention because I sure don’t think of him that way.
I did say that he was approached by some women in the past, which is very different than saying he was offered sex all the time. I mentioned that because in my OP I had said that he had the opportunity and turned it down and some people had wanted some more information about it.
And everything else I’ve said is true, he doesn’t have a job, he does live with his mom and he is a virgin. Had I stated his entire life history in my first post, I doubt anyone would have even read it.
If somebody asks for clarification, I want to give it to them so they have all the facts. I’ve been completely honest here because I am sincerely seeking opinions about it.
I’ve gotten some really good feed back too.
Yikes. What fantasy? Oh well.
I really do appreciate the thoughts and advice I’ve gotten here.
That he is some sort of diamond in the rough.
(thanks for the catch, Indistinguishable)
I don’t think that at all. He has major issues. But those don’t make him a pathetic loser either.
Anyway I likely won’t read anymore replies here. I have issues as well, one of them being that I’m overly sensitive. I really wrote from my heart here and was completely honest. So to be called disingenuous when I’ve been extremely genuine is quite upsetting to me.
Forget the nay-sayers, do what’s in your heart. Like I said, nothing is set in stone. If it doesn’t work out, then it doesn’t. Just don’t get all co-dependent, know when to stop (but you may already know that).
Have fun 
I don’t think you’re being disingenuous. I think you’re just trying to put the best spin you can on his shortcomings. Don’t take that criticism too much to heart. We’ve had posters in the past who have trolled by slowly altering their stories before, so people are alert to the possibility. I think you’re just trying pull back a little and say “he’s not THAT much of a loser,” just because you’re starting to feel defensive of him.
To me it sounds like you like him, you value him as a friend, you want him to have some kind of a shot at a love life, but you also know he isn’t Mr. Right, and you aren’t going to marry him or anything.
Ask yourself this – if he called you or IMed you (or whatever you guys do) and told you he’d met a girl, and started dating her and thought it might actually be going somewhere, would you be jealous, or would you be happy for him (maybe even relieved)? If your answer is the latter (which I suspect is), I think that tells you what your relationship to him really is. He’s a friend.
Possibly with benefits.
Years ago I had a psych prof who was talking about extratensives and introversives. She explained it like this:
Suppose you gave someone a cardboard tube, a ball of string, some glue, (etc.) and said, “I want you to make a labor-saving device out of all this. Go!” Some people would stare at the materials, chin in hand, and imagine what they could do with them. Other people would pick them up, examine them, start trying to fit them together, hold together different pieces in various configurations, etc. Short story long, some would attempt to solve the problem in their brain first; others would start manipulating what’s out there.
I tend to be introversive and I’m reading a lot of that in the OP’s description.
I recently met a woman. Petite, dark hair, dark eyes, meets all the wish list WRT physical appearance. She’s ok…but looking at her doesn’t rock my world or anything.
I recently met another woman. Also petite, dark hair, dark eyes, meets all the wish list WRT physical appearance. Man, she’s fine. I mean, WHOA!
My point is that they fit the same description but my reactions to them are miles apart. If someone tells me on the phone, “Hey I’d like you to meet my friend; she’s petite, with dark hair and dark eyes,” which one am I getting? And that’s just physical stuff. When you’re dealing with basic facts (the job issue, living at home, etc.), you can carry them in any direction you like with your imagination but never really know what it means.
So I think the OP should stop trying to solve the problem with the imagination and be more extratensive, get some feedback experientially.
It seems like an extremely low-risk situation all around to me. If the guy has talked to you for ten years, clearly he isn’t just trying to get in your pants, nor is he a stalker or whatever. He values your friendship and if you meet but there are no sparks, that friendship will continue. Meeting face-to-face will likely tell you what you need to know, whether it’s worth pursuing or not.
FloatyGimpy, please don’t stop reading or posting. Of course you’re defending your friend when someone talks smack about him, that’s what friends do. And I do understand your sensitivity, but do remember that we’re all essentially strangers. While we all know things about each other, none of us really know each other, and we just all throw in our advice and thoughts from our own frame of reference, which can come off as overly judgmental.
It’s a difficult situation, that’s certain. It does seem to me that he has you up on a pedestal, and it’s hard to be up there and manage those expectations even while being perfectly clear on what everything means to you. There definitely is the possibility that you’ll end up hurting him either way. And that’s something to think about.
On the other hand, life is too short. We’ve had gobs of threads talking about “don’t wonder what might have been - go for it!” And really, at the end of the day, all you can be responsible for is you. You can’t be responsible for him. If you think it’ll be a fun weekend with fun experience that will make you smile, then I think you should go for it.
Best wishes to you.
I think, at this point, several things are clear
A) You’re going to go for it
B) It won’t work out great in the long-run
C) You already realize all of this, at some level
So, uh. Go for it. But understand that it won’t work out great in the long-run. It might still be worth it or not, I guess. You’ll find out.
One thing I hope you realise: This guy is going to have HUGE expectations. You know how sometimes people will build up their fantasy idea of how a date or experience will go? Times that by a million and you will have this guy’s expectations.
Tread very cautiously.
You are not. Everyone can relax now, I am here.
So let me see if I have this straight:
Should the OP date a 40 year old virgin hoarder with social anxiety disorder who lives a geographically undesirable 4 hours away at home with his mom, has trouble holding down a job and who you’ve only known online for ten years and have mostly thought of as a friend?
Ok, well on paper, this guy certainly doesn’t seem like much of a catch. But you seem to like him so what’s the downside of seeing if there is a love connection there? Best case, you are in a long distance romantic relationship with a somewhat eccentric guy. At worst you lose what IMHO is a very superficial relationship with a weirdo.
Basically, I say go for it. But I’m more of a risk taker learning by doing sort of guy.
I’m curious how they even approached dating in the first place (both one another and in general). Has he ever asked her advice? Did she let him in on the details of her marriage and her divorce? Have they both been lamenting being single?
And why haven’t they met in person before, as friends, instead of waiting until there may be something ‘more’? (‘More’ being what could be a short-lived attempt at dating versus 10 years of online friendship. Definitions may vary.)
Also, I know nothing about the OP, but while at first I thought it was cruel to put her in a position where she basically has to tell this guy ‘Now that I’ve met you in person, your looks repulse me/aren’t so bad/make up for everything else,’ I remembered a dating truism – beggars can be choosers. He does sound doting and perhaps even desperate but (again, knowing nothing about the OP), who’s to say the encounter wouldn’t end with him telling her she’s just not worth driving four hours for?