Does this relationship sound like it could work?

We are best friends, and have known each other online for over two years. We have quite a large age gap, but it hasn't been a problem as I haven't had much life experience compared to my peers and he is wise for his age, so it feels like we are much closer in age than we are. We are very close, and we text everyday for anywhere from two to five hours altogether. It has always been like this. We both have severe forms of social anxiety, and met on a forum for that. We decided a while ago that we wanted to be in a relationship with each other one day, which I have been very much looking forward to. We have video chatted and voice chatted (only once for each so far, but we are hoping to do that regularly) and sent videos of ourselves to each other. I regularly send short audio recordings to him which have been getting longer. He has helped me improve myself a lot, especially in the last few months, and I have been getting better at expressing myself to him, which he has been happy about. I want to improve myself as much as possible for him. He's always there for me, is very sweet and understanding and is everything I want. He even bought a stuffed animal that he plans to give to me when we meet in person. We are scared of losing each other due to any problems that could be caused by the Internet where he lives, or for any other reason. He needs lots of reassurance that I will never leave him. I accept him the way he is, even with any flaws he might have, and he says he accepts me, too, despite some requests to work on my body, which I was happy to do as I was already planning that. I regularly write handwritten letters to him (sent online) to remind him how special he is to me. We have pet names for each other. He even hugs his pillow and says goodnight to it, pretending it is me that he is cuddling all night. All along, he has kept changing his mind about whether or not he wants to be with me because his feelings for me are never permanent, and I know that's probably a bad sign. He is ashamed of this, but he looks at other women a lot, and sometimes feels sad because he thinks women like that would be out of his league. He saves photos of women and then deletes them due to guilt and feeling disloyal to me despite the fact we are not in a relationship yet. He can be very interested in me, then lose his feelings and feel nothing, having to convince himself that I'm what he wants. He has said he doesn't know what he wants more than once, and is sorry because he doesn't think it's fair to me. He also fantasises of me being with other men and admitted that he fantasises about that more than me and him, even though he feels as though it's wrong and wishes he thought of me and him instead. I think that might be another bad sign, but I'm not sure. I would like to think the person I'm with would hate the thought of me being with anyone else. I live in Australia and he lives in America. He talked to his mother about me last week, and she said she doesn't think it's a good idea for us to be in a relationship because he might not be happy for long with me only visiting, but that it's only her opinion. He agreed to a point, saying he probably wouldn't be happy to go possibly long periods of time without seeing me. He has said I would need to promise to do everything I could to become a citizen of his country and live with him permanently because he wouldn't like me to only be able to visit, and would want me there forever. I didn't realise that I would be expected to move (I thought we could do regular visits) so my idea was we could spend about a month or two here together and a month or two there together and keep taking turns, never being apart, because I know neither of us could ever move to another country and leave our families, and we wouldn't really be able to travel alone. We haven't met in person, and he said he wouldn't expect me to move until after about the third visit. I know my idea wouldn't be sustainable and would get very expensive, but I don't want to admit that to myself. I have been reading lots of quotes about long distance relationships and read articles about how to make it work. When I read those, I feel positive about it, thinking "We can make it work. :) We already do things like this, anyway." I told him this, and he says we can try, and he wants to do whatever it takes. We promised each other we would do what it took, but that was when I was thinking my idea would work and I could manage to find a way that neither of us would have to move permanently. His mother thinks he might only want me because he doesn't know other women due to his social anxiety and the fact he never socialises and has no friends in real life (I'm in the same situation). He wants to get better and push himself to start socialising, and I'm scared about the thought of him finding someone else. I love him, and I know I could never find anyone else like him, so I feel sad and empty about letting go of my wish to be with him. I don't trust easily, but I trust him and know he genuinely cares about me. I don't know what to think. :( If this relationship happened, does it sound likely that it would work? I feel empty as he is truly everything I would want and due to my current situation, finding someone else would not be as easy as it would be for most (my anxiety leaves me unable to speak to non-family members and anywhere outside of the home). Sorry for such a long post.

Hi Sundaythe26th, Wow. Well first I want to say I realize it's tough to deal with social anxiety and I realize it was probably difficult for you to reach this point with someone else like this. It isn't easy. So I'm glad you've had this person to help comfort you and brighten up your days for these past two years. I'm not sure who is the older and the younger of the two, or how large the age gap is. But I feel like I can provide you with some feedback from experience. I don't want to drone on, but I'll tell you a few stories to get to the point: When I was younger I didn't have a lot of friends in school. It was around the time I started high school that I started using the Internet more, and communicating with people on forums and in chat rooms. I made a few online friends over the years but struggled with the concept of whether what I had with these online people qualified as being "friendship". One of the earliest people I met online, somewhat ironically, was an older girl from Australia. We didn't talk for very long, just a few months, but we kind of "dated" and talked every evening (morning where she was) and I still think she did open up about some things, like the pressures she faced from her strict and successful family. Of course there was also a lot she didn't tell me, and some of the other people who went to the same website as us brought that to my attention. To her I was just a distraction from her mundane life, and after we stopped talking she went on to several other distractions. I haven't talked to her since then, and that was about 16 years ago now. Out of curiousness I looked her up more recently and saw that she is happily married with kids, and I was happy for her. I hope she found what she wanted. A few years later, probably midway through eleventh grade or so, I started talking to another girl from the US. She lived a few states away, South of me. As I became estranged from the few friends I did have in school yet, I became closer to this girl, and was attracted to her uniqueness. This girl has Asperger's Syndrome, and I'm sure that impacted her life a lot more than I'd realized. She seemed very offbeat and cultured, and I thought she was really interesting, and she was also very optimistic and hopeful and would try to cheer me up whenever I was down. In reality I don't know what all was going on in her life. All the way through the end of high school and well into the next year or two after I'd graduated I had feelings for her. We had sent letters back and forth a few times, and she really put a lot of effort into the ones she sent me. All she ever wanted from me was my friendship, though - I eventually learned from a friend of hers she introduced me to that she had been dating the same guy off and on for years, and she had never once mentioned it to me. I reacted badly and we never talked again. I have even tried finding her again just so I could apologize and maybe continue our friendship. Eventually I met my first girlfriend through a chatroom, bonding over something we both liked. We talked every day for months, and within about half a year we met at a museum halfway between where we lived and went on a date. A month or two later she visited my hometown. And over the Summer I visited her just about every weekend, staying at her place. By the end of the year, I moved in with her. The relationship lasted for a few years, but ultimately crumbled for a number of reasons. One of them was a large age difference. Another was I don't think she was my type. But also, because I had never really dated anyone before I didn't really know exactly what I wanted, and it eats away at you when you eventually realize maybe you could have found someone who is a better match for you, and who you don't feel like you're just settling for. When you have low self-esteem and don't put yourself out there, it's hard to believe the right person exists. The fact that this guy is having a lot of doubts and has already looked around a lot at other women is probably not a good sign that this will be permanent. I did the same thing when I met my ex. I also hate to say it to you, but his mother was absolutely right. The reason why he is dating someone online in a super-long-distance relationship is because of his inability to socialize, and likely his low self-esteem. Long-distance relationships, okay, maybe they can work? But they can only work if they don't remain long-distance relationships. There has to be a reasonable time-frame wherein you are both realistically able to meet, and you have to eventually be realistically able to make things permanent and relocate. You also have to ask yourself if it's worth leaving behind your home country and any family and friends to go to some place where it will take a lot of readjusting - in addition to dealing with the effort of a new relationship. And believe me, those do take work. There's nothing wrong with remaining friends with this person and, who knows, maybe there's still a long-term possibility of a relationship with this man. But I would say this is not realistic, and there's just too much you can't learn about human interaction and dating from the Internet. The same goes for dating apps - those actually make things more challenging for people like us! Good luck with whatever you decide to do. But know that you will have to come out of your shell and get to know people in life either way eventually. And, there's a good chance you will meet someone who is really good for you that way.