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Always Been Lonely....

I'm a 27 year old Male and I've never experienced a real relationship with a woman. I'm shy and unhappy with my looks, am overweight, now balding and just general don't look pleasant. This has lead to years of low self esteem and no confidence, especially with women. I'm still a virgin as well, and while it's not sex that I'm seeking, the intimacy involved is part of what I desperately want. Even people who would be considered unattractive by most, or have other 'problems' seem to be able to get with someone for a little while at least, but I just seem to have been a total failure so far.

Most other parts of my life are normal, although I am now back in my hometown and most of my friends aren't around any longer, the ones who are have long paired up, living together, kids on the way, etc so I see much less of them, which in it's self is lonely but mostly it gives less chances to find what I really seek, female companionship.

From the new year I've been feeling really down about this and resorted to something awful. I'd previously tried a free dating site with very little luck and no actual meetings. In March I started signing up with a fake account, the intention being to get some practice speaking to woman should I ever actually get the change as myself. For awhile this went as a harmless (but not fair on the woman I fully agree) experiment, speaking to a woman for a day or two, just practicing general chat and flirting a bit, but the conversation would dwindle out before it went anywhere, then I'd remove the profile before anything happened.

I did this a few times in different cities and found it pretty easy to strike up good conversations because the photos were of some gorgeous fitness model type, but unlike most guys on there I wasn't after cyber sex or naked photos, I went on there with my own personality and wanting what I want in real life, a woman to actually chat with and look for a relationship with. Of course the (I know see) inevitable happened, I got too close with one woman, speaking pretty much 8 - 12 hours for 4 or 5 days and it just got too deep before I knew what was happening; Not as if we are both in love or anything, but easily we were at the first date stage. Of course I had to end it and couldn't think how so I just deleted my account and email address.

I feel disgusted with myself over this, I always felt guilty for doing it every time I came off, but without the communication I feel so lonely, even though it's not really for me it some how keeps me going. But this time I am truly hating myself for probably hurting this woman who was truly wonderful; beautiful, intelligent and friendly. I'm sure if anyone replies I will get well deserved hate for doing this, but it doesn't matter because you couldn't despise me more than I do myself at the moment. I want to send her a apology e-mail kind of explaining, I don't want to have messed her up with trust issues and I suppose I just want her to know I wasn't a total pervert, just weird in another way.

I don't really know why I'm saying all this, and sorry if it makes little sense as I haven't re-read it, it's just come out naturally as I sit here depressed, lonely, and even wanting to go back on the dating site just to have some pointless conversation in my life (I've sworn I won't do it again). I'm trying to improve my life, I'm working out and eating better, I'm taking driving lessons and planning on moving back to a city which suits me much more... but it's like the more I do these tasks to get towards my goal, the more depressed I am that I'm not there yet, and of course none of these things guarantee the self confidence I need and the loving relationship I seek.
xfakex xfakex 26-30, M 1 Response Apr 12, 2012

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I'm overweight as well tried the whole online dating through free trials and what not. I posted pictures of myself but only really flattering ones :D. I only had a connection with one guy. We were matched and once we exchanged numbers he sent me a picture. I have to admit that based solely on our conversations, I was happy. When I saw that picture, I started pulling back. I couldn't imagine having a relationship with him based on his looks (I'm horrible, I know). He always texted or emailed me first but I never fully engaged him, so eventually the conversations dwindled out.
I hate to be so concerned with looks (especially since I'm no beauty queen either) but I feel I need to be attracted to someone to be in relationship with them. Is that so wrong? Maybe it's my optimism, as I'm 22 and still hopeful of losing weight and finding someone I can be attracted to and that can be attracted to me. Anyways, I've been rambling.
I understand why you felt the need to post a fake picture. I'm always feeling lonely and tried the online dating thing. I kind of wish I never saw his picture, to keep the conversation going (even though I know I would have to see him eventually). I've actually thought about doing experimental online dating and sending fake pictures just so I can get my confidence up. I've never been in a relationship and I want to be prepared for the real thing as most people my age have been through that whole awkward phase.
For now, I'm working on my weight and image. I start working in the real world in about 9 months. I'm also really shy but maybe a new image will boost my confidence. I know this is an old post, but I hope all this has gotten better!