over 40 dating

Midlife daters have admitted to me that they don’t know how to flirt anymore. Some even say they never knew how. Now that they are single in midlife, they are feeling they need — and want — to learn.

But how does one practice? Chatting up strangers in the grocery store? Smiling and winking at others in the gym? Offering, “You look familiar” to someone at the coffee shop?

Instead of strangers, should one practice on folks you think are single at church, school events or work? What if they aren’t single and they think you’re being inappropriate? If your flirting backfires, you’re stuck seeing them at future functions.

So what’s a neophyte flirter to do?

There are various types of “buddies” in dating. Some you’re good with; others you’re not. You don’t really want a  no-strings-attached sex-only relationship. You want some strings if you are going to get intimate — at least some interest in exploring if you both want there to be strings, not just “That was fun. See you later.”

You crave tender touching and caresses, but there’s no one on the horizon that interests you enough to go down the physically intimate path. So you seem caught between no physicality at one extreme to enduring a booty call just to get some physical contact.

I’m struck that many men’s online profiles say they want a spontaneous woman. It’s made me look at my own level of spontaneity.

My experience of spontaneity is that someone else (a friend or suitor) calls or shows up and says, “Hey, I’m on my way to XXX. Wanna come?”

The attractive mature woman approached me after my talk on dating after 40. She said she admired my courage to take on dating so enthusiastically, but she was afraid to start dating.

I asked what her fear was.

What determines if you are an item? Is it agreement about exclusivity? Is it the fact that neither of you is interested in seeing others?

You may think that his regular calls, texts and weekly dates makes him your beau. He may think that you are just one of the women he is seeing, even if at the moment he’s not seeing anyone else. You may feel that by your sleeping together regularly, you are going together. He may feel that you are a woman he’s hanging out with.

You’ve struck up a nice communication with a man who seems to fit many of your criteria. He’s smart, educated, polite, funny, well traveled, successful and clearly interested in you and your life. His age, height, and economics are in the right range for you. You’ve talked on the phone several times and you’ve had email, IM or text conversations every day for a week.

You usually like to meet a man in person within a week or 10 days — before spending too much time flirting virtually. You know it pretty much all hinges on how you feel about each other face-to-face. It can enhance your growing fondness toward each other, or it can fall flat.

With a first date set for a few days hence, for whatever reason (business or family illness) your guy is suddenly called out of town. You understand — he must go. But it happens too quickly to fit in even a coffee date to meet.

I’m an equal-opportunity dater. I’ve gone out with Caucasian, Black, Latino, Asian, Indian, Native American and mixed-race men. Although it doesn’t always come up, I know some have been Christian, Jewish, Muslim, Buddhist, Hindu, agnostic and atheist. None of these on their own are deal makers or deal breakers. My interest or disinterest depends on many other elements.

So it surprised me when some Black men asked me if they are an “experiment.” If going out with them was part of satisfying some curiosity of mine. The first time I was asked this I was confused, so probed.

“What do you mean by ‘experiment?'”

(Read about our first encounter)

A few days ago he returned from his global travels and was in my city for a few days. He remembered that my birthday is today so he decided to treat me to an early birthday celebration. He’s still handsome and buff at 61, but perhaps not as much as when he posed for Playgirl 30 years ago.

In addition to his good looks, he’s attentive, intelligent, humble and funny. I briefly thought of abandoning rationality and suggesting a romp in the hay. I’m pretty sure he would have been game. But then I remembered that trysts are like Chinese food — soon thereafter, I’m hungry for something more substantial.

Here’s a recent question from one of our regular guy readers. I thought you might have some suggestions.

There are usually inequalities when you are dating. One person has a more successful career. One person is better at interpersonal skills, and the other is better at technical skills. Differences that makes life interesting and the world go around.

We are both past the having babies stage, but I wonder about the inequality of our families. All the kids are old enough that they won’t be living together. But, I just started wondering if the inequality will bread resentment. I can provide a husband and a house. But for kids, we will have to play the cards that have already been dealt.

Hair.

It can either be a source of pride or vexation. Women typically either love or hate their manes. If a woman’s tresses behave as she desires, she’s very happy. If not, she bemoans her bad hair genes. Sometimes both in the same day.

What does a woman’s hair have to do with dating? A lot, it seems.

He’s tall — 6’3-1/2″.

He’s dark — with a perpetual tan.

He’s handsome — drop dead gorgeous.

He has a deep, sexy voice.

He’s funny, humble and adorable.

He’s athletic — a former NFL player.

Our 19-year age difference doesn’t seem to matter.

There’s only one problem…