What It’s Like to Date Rich Men and Poor Men

My grandmother told me, “It’s as easy to date a rich man as it is to date a poor man.” Or was that marry a rich man? Anyway, I’ve dated both indiscriminately. Some own airplanes and yachts. Others have a shrinking checking account and ramen noodles in their cupboard. All I really care about is their looks … I’m only partially kidding. I prefer that my dates look like neither my grandfather nor my 21-year-old son. A new you within reach …

Why I’m Thankful About Dating

Interview 100 people currently engaged in dating and I suspect the majority would say, “This sucks.” They’d complain about the games the opposite gender plays with their head, body and soul. They’d complain about the dishonesty permeating the process. And they’d complain about the time and expense committed to spinning wheels and not finding true love. Having participated in online dating, on and off, for nine months, I’d agree with these sentiments. I’d also add inappropriate online behavior to the …

Who Wears the Panties in This House?

Q: I am a 50-year-old male. I shave my legs for various reasons, and my wife is OK with it. (She’s even told me how sexy it is in bed.) I also wear thong-style and men’s nylon underwear. Now I’d like to start wearing satin women’s underwear. How should I bring this up to my wife? It seems she’s already somewhat supportive. A: Quite a few men derive pleasure from wearing women’s clothes, especially bras and panties. Before you broach …

How Men Date — and Women Should, Too

OK, ladies, let’s look at specific male dating behaviors and identify which ones might work for us, too. Here are a few of my favorites from the book How to Date Like a Man by Myreah Moore. A guilt-free numbers game. Men feel completely guilt-free while dating women simultaneously. Dating multiple men left me feeling a little guilty. But then came the man who, on just our second date, said he quit an online dating site after meeting me and wanted me to meet …

My New Strategy: 6 Dates, 5 Men, 1 Week

One man I was going out with said that men date different women simultaneously to find the most appealing one. Others tell me you have to kiss many frogs to find your prince. So I finally decided to spice up my sequential dating “strategy” and try dating more than one man at a time. This past week I went on six dates with five different men. Three were blind dates from an online site and two were men I’ve been …

How a Woman Can Date Like a Man

A recent first date was quite forthcoming. He suggested that I date like a man. As a man, he dates multiple women at the same time and whittles away those he doesn’t like until only one he likes remains. He referred to the women he’s dating as his “harem.” It turned out that I became the woman he finally selected, and to no one’s surprise, the relationship didn’t last long. It did, however, plant an idea. Why can’t a woman date …