Missy, I'm a successful businessman with very little spare time. I travel a lot for business. I'm in my late thirties, fairly good looking, not in bad shape but no athlete. I dated a lot in college but once I started the business I couldn't keep a relationship. The usual complaint is that I'm not spending enough time or not giving enough of myself.
Well, I admit I'm probably married to my work.
I have a few thousand a month I could use to keep a woman. How do I meet a woman to be my mistress? I have to be attracted to her, she should be smart, mostly she can't mind that I'm gone so much.
Lenny - Chicago
ANSWER FROM MISSY
Lenny, very few women like to be alone a lot and in a relationship, but if there's any kind of woman who can stand it, she's a very independent woman who has a life that doesn't include you so much, someone who has friends and activities, work or a career of her own. In other words she is not going to sit home alone and be on call for you or make you a priority unless you make her yours!
I wonder. If you met such a woman and things were good in your relationship would you want to marry her?
Are you only thinking about having a mistress because you are sure you do not want to marry for reasons besides all this business busyness?
How to meet a mistress?
There are various opportunities on the Internet - dating clubs and such - which I don't believe in because I believe in meeting people in the course of life! I believe love at first sight can happen too! It concerns me that many of these hook-up sites are simply prostitution.
If you cannot make at least one night a week to do the usual - going out to meet people - then you cannot make at least one night a week to spend with your mistress when you're in the same town! If you can't see someone once a week, it's probably not a go. So one night a week go out.
Go here, there, and everywhere, activities you enjoy, and don't be shy about saying hello and introducing yourself to women you see out who is also out alone. You may hand a woman your social card, which is like a business card, but which has your full real name, and your home phone number on it, but at the same time you MUST ask her for hers! Don't tell her to call you if she's interested. Women are still feeling a man ought to make a first move - lead the relationship. YOU SHOULD CALL HER and ask her to meet you for lunch on a weekend (or day when neither of you have to make that lunch a rush before getting back to work).
At lunch start to get to know her as a person through conversation. DO NOT MAKE LUNCH INTO AN INTERVIEW! Do not hit her with a dozen personal questions or ask her if she wants to be your mistress even if she's the most beautiful woman you've seen in years! ALSO LISTEN. Many men make the mistake of talking about themselves - bragging - for an hour without showing any interest in the person whose been listening.
Remember that you're looking for a RELATIONSHIP with a PERSON, not a hook-up! Whatever that relationship will be, don't just jump in. If you do not feel more interested in her at lunch, well, she may be someone you would like to invite to a party so that your friends can meet her. Don't make wild promises or tell her you are not interested. Think about it and ask her out to lunch another time if you want to advance the relationship a bit.
It's funny how things can change when you do!
Missy
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