older women dating younger men

A good pal was telling me about a middle-aged, tall, athletic, single lawyer friend of his. I said, “He sounds like someone I’d like.”

My friend responded, “I don’t think it would be a good match. He likes to wear the pants in the relationship.”

I was taken aback.

Bev asks:

“How does a woman over 50 whose divorce settlement made her a millionaire + handle dating when most men will not have anywhere near her net worth?”

My mother would refer to a single, traveling ladies’ man as someone who “had a girl in every port.” Just like many of the sailors she knew as a young woman.

Now, as a traveling woman yet to find a local man I want to date regularly, I’m finding I have gentlemen in various parts of the country. I saw a favorite for a drink in his local airport hotel bar during a 2-hour layover yesterday.

At my professional association conference last week I got a lot of attention. I was very visible in a number of sessions, so had a lot of people acknowledge my contributions. In one session, I made a joke about looking for dance partners for the gala.

About a dozen men came up to me afterward saying they wanted a slot on my dance card. I smiled and agreed.

Karen writes: “I am afraid I am too assertive. I start taking the lead when the man won’t or doesn’t. I see simple solutions (where and when to meet) and make suggestions. Is this really a bad thing?”

When we are younger, with our lives yet to be determined, we can fall in love with someone’s potential, not who they are at the moment. I know I have.

A pal wrote today, “I have fallen in love more times than I care to count with the highest potential of a woman, rather than with the woman herself, and I have hung on to the relationship for a long time (sometimes far too long) waiting for the woman to ascend to her own greatness. Many times in romance I have been a victim of my own optimism.”

I have two 23-year-old women in my life who are both in bad relationships. This is not only my perspective, but they, themselves, often complain about their partners. Their mothers and sisters agree (the fathers aren’t around).

However, their partners know just what to say/do after a blow up to keep my friends around. Each of the women’s partners are immature, self-absorbed, manipulative, and lazy, leaning on each woman to supplement their meager income. There is some verbal abuse. When between jobs, instead of earnestly looking, they are distracted by video games, TV and goofing off.

And the cycle continues.

A friend shared that she was too naive after her decades-long marriage ended. She was clueless about not only how to be with men other than her now-ex-husband, but about how she could be harmed while she learned.

Deb writes:

“I have had 4 dates with one man and I find him very interesting, funny, smart and a gentleman. How do I tell if he is really interested in me? I have read books and everything says to play a game, acting like you are not interested and he will come after you. I want an honest, open and upfront relationship. Do I tell him that I like him and flat out ask if he feels the same. Or do I go with the game of acting like I am not interested?”

Ah, Deb. The age-old question of, “Do I turn him off if I show I’m interested, or pretend to be aloof and coy in the hopes of enticing him?”

This conundrum has plagued women for decades (nay, centuries?).

A recent conversation with a guy pal was startling.

He’s a smart, goal-oriented, ethical, solid-morals, middle-class guy. So I assume he hangs out with other like-minded folks. But apparently not so much.

Since my divorce, I’ve had a fear of dance classes. Not because I’m concerned about following the steps — I’m reasonably adept at that. But it’s for another reason — something that I think might plague other accomplished women.

It might be something that you struggle with yourself.