There are two topics which women should never discuss in a new dating situation: (1) the exact number of men on your list of former lovers; and (2) your salary.
Young women especially should take heed to this advice. If you reveal to your new man that he isn't your first love or that you make more money than he does, your name is MUD. Young guys tend to flip out and go crazy when they hear this wonderful accomplishment; older guys don't handle it especially well either, but they are more realistic. Some guys just can't resist asking a question when they know full well they don't really want to hear the answer. Two cases in point:
Case #1: "I heard that my girlfriend hooked up with this random guy before and that she was supposed to hook up with my best friend. This all happened before she met me. She never did hook up with my friend, but it is disturbing to me to picture her and him together. I am kind of stuck on it. I don't think I could break up with her, but it would just make it easier for me if I could stop picturing her with my friend or anyone else. I just want to get over it. Please help!"
Case #2: "I am engaged to a 27-year-old woman that refuses to tell me how many men she has been with. The only thing she will say is that it is between 15 and 20 men. I don't know why, but I am upset about this. I mean, I really want to know how many men she has been with. I have told her everything about my life, including the women I've slept with. I want to know the same about her. What should I do?"
How about you stop asking? Why a man would even entertain the thought of asking such a question? Obviously the answer is perilous to his self-esteem and mental stability, so the need to know the answer in this situation is beyond my understanding.
Men are very competitive by nature. They want to win and be the best at everything. This somewhat explains why the average man would attempt to size himself up by comparing his prowess to your past loves. But to do this well, he has to know how many men he is besting…therefore he asks how many men you've had. If it turns out that he's not your first or at most second lover, he's likely to feel insecure. Instead of focusing on optimizing each other's loving style, some men become fixated on comparing their loving styles with that of former lovers. Major tension, fights and eye-rolling repeated questioning follow. If you make the mistake of responding to his first question with even a tidbit of information, he will never stop running mental tapes or comparing himself to other guys. Watch: Sexual History: Does it Matter?
Paradoxically, women have been socialized to highly value a "manly" man of great romantic and sexual experience. This man has been around the bedpost a time or two and can boast honestly about the number of women he's seduced, becoming the admirer of less successful men and other female conquests. Think of Sean Connery as James Bond for a perfect example!