Dating-over-40 advice by the Dating Goddess™
He is smart, funny, charming, good looking, worldly, educated, successful, a sharp dresser, good listener and conversationalist. He tells you what you long to hear. He is vulnerable with you and you with him. His kisses and caresses make you feel what you haven’t felt in a long, long time. He tells you how sexy and adorable you are, and how much he misses being with you.
You met through business, not online, so you know he’s not a player.
Yet there are things about him that on paper would be deal breakers.
I dated a sweet man who grew up in an African village. He came to the US at age 19 to go to school.
I loved hearing his stories of growing up in his village, living in mud huts, bathing in the nearby river, gathering water from a pond, making fire from sticks and moss, walking miles to sell eggs and chickens at the market, and other examples of a life I couldn’t imagine. He regaled me with his tribe’s welcome-to-manhood ceremony and other rites of passage.
The phrase “keeping it 100” comes from “keeping it 100% real,” meaning being 100% honest. It’s shorthand for no BS, don’t tell me what you think I want to hear, tell me the unvarnished truth. Don’t hold back.
I decided to try this with a man while we were exploring going from pals to more. His life is complicated right now, uncoupling from a long-term relationship. I wanted to understand his emotional state, goals and desires. I needed to determine if it made sense to become closer during this challenging time, or whether it would be best for all if we stayed pals and revisited becoming romantic after he was fully unencumbered.
A man may enter your life who does not hold the work title or financial status you are seeking. But he’s a good man. He is honest, has integrity, treats you respectfully, listens to you, and is accommodating to your desires.
The “what” is his profession. The “who” is his character, values and behavior.
It’s commonly said that women try to change their man into someone more to their ideal. Men, however, are afraid women will change, as they like what they have.
Not that a man can’t wish a woman was a better cook, was more punctual, neater, or had other habits he liked. But (generally) he won’t hound her, unlike women (generally).
My experience is men won’t tell you when they are fully accepting of who you are, warts and all.
My ex learned he had cancer 2 years ago. Since we didn’t keep in touch, I learned of it a year ago. He did semi-weekly podcasts for a few dozen friends to update them on his health. I listened to the previous 100 podcasts before reaching out via email.
He said he was thrilled to hear from me and was stunned that I would listen to all 100 previous podcasts. I’d asked if now we could be friends and he said he’d like nothing better. We exchanged a few emails and he said he’d like to talk about the end of our marriage as he was sure I had some questions — which I did. I asked for some good times to call since he was so overwhelmed with treatment appointments and recovery. However, he never closed the loop to set up a call, so I decided I’d make the 600 mile trip to visit him and have that discussion face to face. A few months ago, his doctors had given him 18 to 24 months, so there was plenty of time.
When I’m smitten, or even in the beginning of a budding relationship, I think about the guy a lot.
“I wonder how his day is going. Should I text him?
“I should ask if he wants to come over for dinner Friday.”
“I need to ask him why his marriage broke up.”
“I think I’ll ask him to accompany to the party next weekend.”
This sort of incessant chatter fills my idle thoughts. I rarely have time to think of my other interests.
He was not classically good looking. He had a pronounced nose and craggy face etched from decades of intense work. But his entrancing blue eyes made everything else fade away.
He stood straight so his fit 57-year-old body seemed decades younger. And when he looked at you, it felt like he really saw you. He listened and asked intelligent relevant questions. The combination was sexy — my married gal pals felt it too. He was divorced.
We met speaking at a conference in Singapore. We spent all our downtime together the next 3 days. I invited him to a small dinner party with some of my pals. He got along with them beautifully, balancing listening to their stories, asking questions and sharing his own experiences.
But alas, it was not to be.
Both genders say confidence is one of the most appealing attributes in a sweetie.
However, there is a thin line between confidence and arrogance. Certainty is part of both. Here’s an example of when certainty turned unappealing.
Wooing can be exhilarating, fun, and exciting. It’s nice to be the recipient of a man’s attention and affection. It’s especially nice when he’s good at it, but not so good it seems practiced.
I’ve been the recipient of good woos and not so good ones. The latter wooers seem clumsy, perhaps out of nervousness or lack of confidence. The former seem relaxed; the wooing feels natural, comfortable and sincere. But of course, that could also come from frequent wooing.
I’m on an 11-day cruise. It’s not a singles’ cruise. Am I here looking for love?
One of the unexpected experiences of dating after 40 is when someone you dated dies. I’ve had it happen twice now. Of course, death occurs at all ages. It’s just shocking when it’s someone you have met and become even a little fond of.
We all have stories of some date gone awry because your companion acted strangely. In fact, we love to regale our friends with these stories whenever mid-life dating enters the conversation.
We never see that we might have been the one someone is telling a story about. How could we be the focus of a wacko story? It can’t be true!
But it is.
I spent some time recently with a mid-50s, never-married, long-time friend. He’s been in relationships lasting a few years, but never found someone he wanted to be with long term.
But he does love women and he loves to date. He had 3 dates last weekend with different women. He said he liked all of them but only planned to see one of them again. And he had another set of women lined up for the following week.
I asked why he didn’t just focus on one.
I just returned from 3 weeks in Thailand and Laos. My dating life never seems far from my mind. Here are some examples of a few of the activities that reminded me of my dating life.
Do you ever feel sad at missing expressing a part of who you are? Maybe you love to paint but either don’t have the time or space to do it now. Or maybe you love to swim but you live too far from a pool to do it regularly. Or maybe you are exhilarated by snowboardng but live in Kansas and don’t have the means to get to the slopes.
I was feeling this way when it became clear a new guy wouldn’t evolve into a dating relationship. He said he wanted to take me to dinners, galas and dancing. I thought of my dating wardrobe — flattering evening wear, fun, short skirts with cleavage-peeking tops and other flirty attire. I don’t have a lot of opportunities to wear these clothes since I’ve cut back on dating.
