Do I Intimidate Men?

Dear Rachel,

I am very successful in my career and earn a high salary. Since I am 47 and never married, I have been able to buy many luxuries for myself, rather than spend my money on nannies or kid's orthodontics or minivans, like many of my colleagues who are married with children. I have a beautiful loft in a posh east side neighborhood, I wear a fur coat in the winter, I vacation at spas and top resorts around the world, and my business card says “President.” However, despite all this, I am often lonely and would love to meet the right man. When I go on dates, I am rarely asked for a second date, and my friends have told me it’s because I intimidate men. I have dated a range of men from CEO’s to plumbers to teachers, but have not found someone secure enough with himself to pursue me. How can I find a man who is comfortable with what I’ve achieved? 

Signed,

Regan
New York City

Dear Regan,
 
I am wondering if your issue isn’t actually that you “intimidate” men, but rather that you come across as “snooty?” With your long list of luxuries and possessions, your letter has an alienating tone that might make someone bristle. I wonder if that is happening on your dates? I have met several very successful career women (and men) who flaunt their status, and not many people actually like them as a result.

First, I want you to do some “market research” (you’re a business woman after all, so you understand the value of this exercise!). Ask for very candid feedback from three men and three women about your personal style. Be sure to select these people (friends, family, colleagues, even your hair stylist?) for their honesty: you are looking for real help here, not self-affirmation. If there are consistent issues that arise with the feedback, take them to heart and try to make some adjustments accordingly. This will verify whether the “intimidation” issue is really the root cause of your dating problem, not an alienating personal style.