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How can I get over my shyness/insecurities concerning women?

Tagged as: Dating, Sex<< Previous question   Next question >>
Question - (5 December 2010) 1 Answers - (Newest, 5 December 2010)
A male United States age 51-59, anonymous writes:

I'm a male, in my 40s, but I have relatively little sexual experience for my age. I've never been married, and I've only had sex with 4 different women. The longest I've been sexually active with a woman is about 2 years. Although I am a successful professional and many women have said I'm attractive, I am also quite shy, and I find it difficult to meet women.

Most women I meet have a great deal more experience than me sexually. I find myself feeling very insecure, wondering if I'll measure up to their prior sexual experiences, etc. My apprehension causes me to avoid relationships to some degree, but this only leads to more insecurity because I never get more experience.

Women tend to assume that there must be something wrong with me when they find out I'm in my 40s and I've never been married. I'd like to get married if I could find the right woman, but my insecurities make it difficult to meet women.

Although I don't really like the idea of having sex with women that I don't consider to be serious relationship material, I find myself wondering if I should just try to sleep with as many women as possible for awhile in an effort to get over my shyness, inexperience, etc.

Any suggestions on how to get over my insecurity/lack of self confidence? (especially with respect to sex)

View related questions: confidence, insecure, shy

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A female reader, anonymous, writes (5 December 2010):

please consider the idea that it is not your lack of experience that is making you insecure, but your insecurity which makes you believe you need many experiences to "measure up"... not everyone believes that you need to go through sex partners like you go through bowls of cereal every morning, in order to measure up as a man or woman ( though I know men more than women get pressured to do this)4 women, is not too few women in my eyes, it shows a man who has some substance... a man who has been with too many women, personally, would repel me... it shows someone with more penis than heart who can go through so many women without finding one to settle down with, a user instead of a lover....

There is the myth that girls want bad boys, well that's not true, only the bad girls do, the nice girls want the nice guys... myself I've only ever been with one man, my husband... he too feels insecure that he's only been with about as many women as you, and I just have to shake my head (he used to hang out with the druggies and derelicts, but he's over those days now) the question you need to ask yourself is which subculture do you want to belong to, the lust subculture or the true love subculture? you want a nice girl or a bad girl? not that its necessarily so horrible if you just want to be someone who flits from body to body like a butterfly from flower to flower... but how much exactly do you personally get out of doing that? you need to decide for yourself what YOU want not what the prevailing pop culture norms that the media glamorizes says you should want... think about it....

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