Again, you are judging yourself from the woman’s perspective rather than your own, and finding yourself failing before you begin. Some women will look at you as a loser if they learn that you are inexperienced.Some women just want to be pursued, and if you won’t do that they won’t like it.
I have never had a girlfriend, or a relationship that has gone beyond two dates (usually my decision or something weird happens). I have never kissed a woman, or really put myself in a situation where I could kiss someone.
I never went to a school dance or prom (even though my parents were not happy about it). I am too nice, and not aggressive in making things happen. This may stem from the fact that I even have trouble hugging people, and saying “I love you” to family members.
I think that I have three problems: #1 – I cannot build up enough energy to go out and meet women. I am not shy in normal social situations, but just going up to a woman and talking to her is not a skill of mine. I am much more comfortable not expressing intimacy to anyone. I would consider myself over 10 years “behind the curve” and I really feel like a loser. I tend to be a “glass is half empty” type of person.
If I go out with someone my own age, I am going to be light-years behind in experience. When you say that you are a nice guy, I wonder if what you mean is that you are a passive guy. I note that you’ve been on dates but have bailed out of the process after the second date, perhaps because you “fear intimacy” as it were (the second date being the beginning of the period when the formation of a relationship becomes a possibility).
Dating someone 18 and inexperienced like me is also quickly becoming, if not already, not possible. If I end up becoming a “40 Year Old Virgin” I will probably end my life because at that point I will have lost my window of opportunity to have a normal family life. There is a passive vibe to your letter, and an undercurrent of fear, and together these two things seem to be making it difficult for you to ask for dates and to build a relationship.