A
male
age
36-40,
*inglesweetguy
writes:Dear Cupid,I have been single for most of my entire life, except for 3 brief relationships of which were not that great. One of those was a setup and the other 2 I met off a dating site. I have never actually asked a woman out on my own. I'm 26 and lonely a lot of the time. At least, I am close with my family. If I wasn't, I'm not sure I could survive. I've been reading material on where to meet women, what to say, etc since I can't seem to do it on my own. When I do gain enough courage to talk to a woman and specifically ask her out (usually for a coffee), I find out she is in a relationship. I feel as if every girl I find attractive is not single and I don't plan on settling for someone I am not attracted to as that is just pointless and will never develop into a great relationship. I guess my question is: How do I improve my chances and how long after talking to a woman is it acceptable to ask her out? I am very depressed right now as the holidays are near. I consider myself a hopeless romantic, a sensitive guy, and a guy that will do anything to keep the women he loves happy. I'll stop rambling now.
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Fancy yourself as an agony aunt? Add your answer to this question! A
male
reader, advisorX  +, writes (8 December 2010):
 The problem i can see with you right now is that you dont have enough confidence to talk and be friendly with women. Dont look for a woman whom you want to be your girlfriend but rather look for women whom you want to be your friends. By doing this you will not only develop self confidence but you will also learn the strength and weaknesses of them. And when youre comfortable with their company you will also learn to socialize with every woman you want and it will be easier to ask every woman for a date.
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