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i'd say about until 30. after that, i think people either think you're gay, are monstrous ugly, have the worst personality out there, or have an emotional problem.
I have a few elderly customers (men) 80+ that have never been married, dated or had a GF. Unless they paid for it, I doubt they aren't? They are very nice guys but aren't comfortable talking to women. They are both studderes, and felt the women would ridicule them over it. That's ridiculous if you ask me. Now they will probably pass on alone and wondering what happened to their life? At least I can make them cut up when I go to their house. Just don't laugh so hard you wet your Depends.LOL.......
I had a friend who was still a virgin at the age of 40. This bothered him terribly. He has a friend who lives in Thailand. I kept telling him to go to Thailand and get it over with. He said he won't pay for sex. At some point, a guy has to do what a guy has to do. We lost contact after it became obvious he had designs on me. It's sad. I really did like him but after he visited me and whipped out his book on "How to score with women," it was all downhill from there. Then he invited himself to spend Christmas and New Years with me (and he lived out of state) so I just had to cut the cord. I still miss his friendship.
I'd say that age 30 for guys is crossing the "point of no return." I lost mine in my mid 20s and that was by far the latest of any guy I know. I was really starting to get worried about losing it after age 23-24 or so. Even now, my experience is so limited, that if I had the opportunity again I probably wouldn't really know what I was doing. Fortunately my first time, the woman was a virgin herself and very understanding of the whole thing.
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