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How not to blow it on a first date.

Posted Dec 01, 2019

It’s a conundrum. Why is it so difficult for my single female age 60 friends to find a heterosexual male friend or potential partner with whom they can (yes, you heard it) take long walks, go to plays and movies, and take trips?

As one of the contributors to Psychology Today lacking letters after my name, I am not about to give members of the opposite sex any hard, fast advice using empirical evidence or citing biological studies.


Source: pexels

However, I feel the need to speak up for the female of the species in order to help form a more perfect first meeting/first date/blind date. Just because I am not in their shoes doesn’t mean I don’t care. In fact, my husband makes fun of me for trying to pair people up, but he also knows it does not deter me. What I am about to say is pure opinion, with a lot of pipe dreams and personal preferences thrown in. Apologies in advance. 

The thing is, most women don’t want much more than a guy who treats them well, makes two-way conversation, and already knows how to take care of himself. So when we meet someone special, it’s as if the heavens have opened up for us. Even looks are not as important as personality by the time we reach an older age. An average looking guy can transform into a veritable George Clooney before our eyes when all else about him works. This usually does not ring true in the opposite direction, unfortunately. We don’t miraculously become Catherine Zeta Jones because we have a great sense of humor or amazing intellect. Unlike men who hope for younger women to adore them, we tend to prefer men within five years of our own age — men we can talk to, walk with, and take anywhere. 

Complaints I hear from my single friends are all very similar when first encounters with older males take place, whether it’s a fix-up or an online introduction. While there are surely still a few gems out there, what I hear is that many, many older single men:

  • Lie about their age and/or their economic status
  • Can’t stop talking about themselves
  • Tend not to show curiosity in who a woman truly is

“It was the same old, same old,” said one of my friends who just experienced the first result from the matchmaking service she signed up for. “The percentage of time he talked about himself was, as usual, in direct proportion to his apparent ego.” I had been waiting at home for news of the meeting, even though I warned her that if she was the one to prompt the face-to-face encounter with a text, it was not a good sign. Phone conversations, texts, and emails can seem promising—perhaps because both parties hope to meet someone special. However, the actual meeting is an entirely different ball game. Maybe it’s nerves. Maybe it’s awkward to meet the woman/man you hoped could be a winner face to face.

What a man may not think about, however, is that even when he has an attractive woman sitting across from him on a first date, she, too, has had a life. She may have operated her own business, been an executive, and had had a marriage that brought her joy and children as well as disappointment and heartache. She may have learned more about life than he has or been exposed to worlds he may never have fathomed. It’s just that he will never begin to know the depths of her unless he asks. He, like she, must consider sex as a bonus, not the main prize. Many older women are not husband-hunting and are far past the point of “settling.” They want companionship, conversation, affection, and whatever else develops from all that. 

Therein lies the rub, so to speak.

Men (and this doesn’t stop in older age, even if the equipment doesn’t work that well any longer) tend to think of relationships in terms of sex much more often than women, whether it’s a function of biology or not. While we gals can dust ourselves off and start over, we need to feel a man has earned our affections. We no longer need a breeder; we need someone who treats us like a prize until we feel comfortable offering a prize. We want men to care about actually knowing us.

I decided to look around for articles about what men in their 50s and 60s are looking for. To be honest, I believe some of the research is skewed; because what men answer in an interview or on paper may be one thing, while what they want in reality may be entirely different. “Single men in their 60s are looking for a woman who is feminine and is willing to help them feel like a man,” says dating coach Lisa Copeland in a SixtyandMe.com article. “Many women, including myself, spent most of their lives competing with men—at work, in social situations and even at home.” She goes on to say that now that we are in our 60s it’s not that easy to back off and relax a bit. 

That’s when she lost me. “Single men over 60 want women who are in touch with their feminine side. They want encouragement, not criticism. They need confirmation, not competition.”

When I read that, my hackles were up. Her research speaks primarily about how men need validation. Women? We must lack that validation gene, but it’s great when we can be admired for who we are and what we’ve done. For us, the brainwashing started when we were young. We may have been taught by mothers or grandmothers that the world revolves around men and that if we were smart, we would make men think they were both in charge as well as the superstars of our lives.

“You’ll never find a husband with that mouth of yours,” my father used to tell me. He married my mother when she was 18 and he was 25, fresh from military duty during WWII. “He wanted a woman he could mold into the wife he wanted,” my mom told me after I had married. When I heard this, I felt abjectly sorry for my mother, who had felt rescued from her own miserable family situation when she married my dad. It wasn’t until her 50s that Mom began to find her independence, taking a part-time job and opening a checking account without my dad’s name on it, for “mad money” to spend on her only grandchild. 

I looked for comments and reactions to the SixtyandMe article to see if my own gut reaction was off-base. One woman who sounded sick and tired of dating sites said, “I think they (men) want to feel younger and choosing a woman 10 or 15 years younger creates the illusion of being not so old.” She also complained that men who called themselves “retired” were either out of work or fairly penniless. 

If you are an older guy reading this (or you have an older guy friend who might need some suggestions) here are a few pointers if you are really looking for that special chick:

Dress for success. If you look like a schlump, women will escape even that first cup of coffee by saying they have another appointment. Even if you hate shopping for clothes, ask a (preferably female) friend for help. Pay attention to your shoes and your nails as well. A professional manicure is a wise investment at times like these. And please. don’t tuck a shirt in unless you have the abs of Brad Pitt. We’d rather guess what’s under those shirttails.

Answer questions when asked, but the point of meeting a woman is to find out about her. You already know all about yourself. You can share descriptions of your own life later. If you both met through a dating site or service, separate yourself from all the other jerks she may have met by not always focusing the conversation on you.

Compliment her on something. Her hair. Her clothes. Her voice. Her smile. Nothing sexual. That’s a turnoff and can also be scary to a woman who is just meeting you. Ever see the movie The American President? Michael Douglas, who plays the leader of the free world, asks his middle school daughter for some advice for a first date with an attractive lobbyist played by Annette Bening. “Just be yourself,” his daughter says. “Yeah. And compliment her on her shoes. Girls like that.”

Don’t lie about your living or economic situation. She is not a meal ticket just because you still feel you have a lot to offer. Relationships are not built entirely on a sense of humor or the ability to recall the scores of the past ten Super Bowl games.

If you have health conditions, be honest about them even it risks getting a second date. Oh, and women our age are usually not looking around for a man to take care of, cook full time for, or fold socks for. Most of us have been there, done that. We want someone to complement our lives and hope men do, too. 

If you don’t feel the chemistry, don’t promise to call if you have no intention of doing so. You can either say it was great meeting her or you are not feeling a connection. Yes. It sounds cold, but at least she will not go home and wait anxiously for the phone to ring or comb her emails for the next two weeks.

I welcome any male contributors here to publish an article on what women can do to improve the odds of a first encounter going well. Men’s impressions of women tend to be brutally visual. For both sexes, however, SixtyandMe’s Angela Page offers the following:

  1. Don’t boast about your credentials
  2. Don’t talk too much about your ex
  3. Try not to be judgmental
  4. Don’t drink too much
  5. Don’t have desperation sex on a first date unless you expect to kick the bucket soon


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