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Comments:
I'm going to be the first female to post in this thread and say that I won't date a man who's slept around a lot. Keep it under the double digits.
As a rule, I try to visit anyone just once. This girl would make me rethink my rule.
Chatting up anybody is fine, and it does build confidence, it is something that you can practice every day. Try to learn to love this human interaction itself and not only as the means to reach a goal, it makes a big difference in how you come across IMHO.
I think you are spot on. My gf even said she likes to please everyone. She hated disappointed this friend, who I guess isn't even that good of friend.