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Seeking love in all the wrong places, Mr. Nice
Dear Mr. Nice,
You do seem to be going about finding a "good honest relationship" the wrong way. First of all, in terms of your fear of upsetting the girl, remember that women are not eggshells--they do not break easily! It's possible that you might not be making your move because of your OWN fear of rejection, not because of hurting the woman you're going to ask out.
When you want to start a "real" relationship that has potential to be long-lasting, move slowly. Think about what you want from a relationship, what you're willing to give, and how much you're willing to compromise. When you find someone you're interested in, ask her out yourself, don't send a friend first to assess the situation. Do not sleep with her on the first date. Spend some time getting to know her, what she likes and doesn't like, what she's about... Ask her out the second time yourself too, and spend the time together doing something that you think she might like given your conversations on the first date. Make sure you both want to have a sexual relationship before you start one. Keep communication lines open, so that you are both aware of each other's expectations and desires. An honest relationship takes a lot of work, much more work than having sex, and being confident that you're willing to do the work will make you more attractive to women who also want a good honest relationship.