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Philippa Courtney



Did I Blow it with the Woman I Just Asked Out?


Dear Philippa,

I met a wonderful woman at a bus stop recently. We both wait at the same stop most mornings. We seem to have great rapport and laugh at the same things. She could stand anywhere but she always stands next to me so we can talk. After I asked her out she said she'd just started seeing someone but we could have lunch or something. She even gave me her email. So, I emailed her and told her more about myself and made fun of the fact that I'm a lot older than she is. Then I stopped by the bus stop one day and offered to drive her to work so she could see I drive a decent car. The last email I sent her I invited her to go to a show with me. No word back and she seemed quiet when I saw her at the bus stop the next day. Did I do something wrong?

�Martin, San Francisco, CA


Dear Martin,

I had two immediate reactions to your letter. If I were this woman I might feel a bit nervous by the intensity of your pursuit�you hardly know each other and there are some nut cases out there. Second, why do some older men who want to date younger women feel that they have to apologize for their age? It implies that they are embarrassed by what they are doing.

I emphasize with you because it must be difficult to find the balance between showing enough interest in a woman yet giving her enough room to breathe so she isn't scared her off.

It sounds like this woman enjoyed your conversations and liked what she knew about you. But, just because a person is upbeat and friendly and you can laugh together doesn't mean that she has the interest, much less the comfort to pursue something romantic with you at this time.

Women are wary and protective these days and you can understand why. In the good old days a man could literally chat a woman up on the street and she would tell him where she lived so he could pick her for a date. A woman would be crazy to do that these days.

It may be difficult for a man to realize that a woman may even fear undesirable phone calls and emails. Even your good intentions and genuine interest can be misconstrued when the woman hasn't had the chance to gain the right comfort level with you.

I believe that all women are flattered by a man's interest, once they are interested. In the beginning it is better to error on the side of showing casual interest than to be perceived as pursuing someone too strongly.

Give a woman time to decide if she's interested. At first, offer her the option to contact you without feeling a need to ask her for contact information. When you establish contact use a light, friendly tone. Frame things in her interest. For example: instead of just saying you have tickets to a concert, comment on the fact she mentioned that she was having a tough week at work and maybe she'd enjoy some good music or some laughs at a comedy club. In other words demonstrate that you are really paying attention to her and you are not just pursuing her as some trophy.

Older men who seem to just go after younger women can turn them off. Most women do not want a guy who sees their age as either an enticement or a bonus. They do want a man who shows interest in them as a whole person. So, making apologies or jokes about your age difference just reinforces the very thing that she doesn't want. If you feel insecure asking a younger woman out then maybe you shouldn't be asking her out. On the other hand, if you recognize how your maturity, sophistication, and worldliness could be very attractive to a younger woman then she will probably feel that way too.

Neither of us can know what is causing Ms. Bus Stop's change in attitude around you. It may not have anything to do with you�I hope that is the case. The best thing you can do is stop�no emails, no calls, no contact�give her space and let her make the next move. My instinct is that you need to let some time go by before she will feel comfortable initiating any contact with you.

It sounds like you have an engaging personality that women enjoy. See this situation as a learning opportunity and the next time a Ms. Right turns up you'll be better prepared to establish contact that you both can feel comfortable participating in.



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