Ending the One-Upmanship that is Middle-Aged Dating
By: Debbie Weiss
Tags: Dating Advice, Relationships, Middle Ags, Empathy, Widow

Ending the One-Upmanship that is Middle-Aged Dating

Photo by Chuttersnap on Upsplash

I’ve been hearing lately from several guys who are having trouble getting follow up dates. My best advice: To find love, develop your empathy muscle.

In my experience, many middle-aged men have let it atrophy.

Why dating is like a law firm.

Let’s go back to the early nineties when I was a young attorney at a mid-sized law firm. So often the conversation among the male lawyers constituted one-upmanship, be it exceeding billable hour requirements, having more accomplished children, or taking self-improvement vacations involving deep sea diving or extreme parachuting.

Some of the more experienced attorneys tried to get the younger associates to work for them, asserting an authority they didn’t really have. My workplace felt like a wolf-pack with the top wolves continually trying to raise their place in the hierarchy.

Talking to those guys was exhausting. I resented having to explain that I couldn’t work for them because I had plenty to do from my real bosses. Their conversational mode of trading mild insults became tiresome. I was a spectator, the guys acting like peacocks trying to see who had the biggest tail feathers, and I became a mud hen looking on.

What’s with all the Insults?

When I started dating after losing my husband in 2013, it seemed I’d returned to the wolf pack. Except this time, it was my dates who were trying to nip at my heels, which was even more disturbing because these guys were potential boyfriends instead of professional rivals.

A large percentage of the guys I dated kept spewing these ugly little put-downs. They told me I should move because they could never bear to live in the suburbs and I shouldn’t expect too much from them and I didn’t understand how the world worked because I’d been married so long.

Worse, they tried to convince me to give up what I wanted. I wanted companionship, with the potential for long-term commitment, not a power struggle. So, they argued that having little time for me was actually a benefit because their work made them so interesting or being non-monogamous made them more loving even though I wanted monogamy. They were like the software programmers who proclaim, “It’s not a bug, it’s a feature.”

I’m a widow, but that doesn’t make me a moron. I can tell when my software isn't loading.

Here are a few incidents that stick in my craw. A man I’d dated briefly came over to my house, looked at my bed (which he had yet to be in), and said, “You should get a king-sized bed, you aren’t a little girl anymore.” That about killed it. I was a wife of thirty-two years who’d seen her husband through cancer. At 59, he’d never even been in a long-term relationship. Besides, it’s rude to criticize a person’s decor. Not to mention their maturity level.

Then there was the over-scheduled guy who suggested we try a long weekend out-of-state together. But a few days before, he could only stay one night because he had conflict, and could I just meet him there instead of our traveling together? When I didn’t want to go anymore, he dismissed me as being unadventurous, failing to acknowledge that he’d turned an already short trip into a very expensive booty call.

Or there was the guy who got way too drunk on date four and regaled me with the story of a young model who allegedly came onto him. When I didn’t like the story, he said he felt sorry for me because I was jealous of her. Meaning he thought I felt threatened because he was desirable to younger women. But his insecurity was really the problem.

I was back to playing the one-upmanship game.

Many of the men I dated seemed like they were seeing what they could get away with and still get laid. There was a conquest mentality, like the old James Bond movies where Bond overpowers and beds the opposing spy (who happens to be a beautiful woman) once she finally succumbs to his overpowering manliness. But Bond was never boyfriend material.

Sex seemed to come with its own contempt, as though I’d been herded, and therefore conquered. But people aren’t territories. We can leave at any time.

Most women don’t have that mentality. We look for connection. What are our similarities? What can we agree on? Sometimes we disparage ourselves to assure other people we don’t think we’re all that. At worst, we keep pointing out our perceived flaws so others feel better about themselves. (“No, look, my thighs are way more jiggly!”) When we get together and one person is elevating themselves while the other is being self-deprecating, there’s no real meeting of the minds, only assertions and deflections.

Our interactions become a power struggle.

But aren’t we looking for a relationship where we grow together and nurture each other? I wanted companionship, not an adversarial proceeding.

I’m guessing most guys don’t mean to do that. They want to appear knowledgeable or worldly or (like many women as well) they can’t help but natter on when they’re nervous. But so often, it all came across as superiority.

After five years of online dating, I concluded that many men of my generation simply weren’t very nice. Or they’d started out okay, but had been damaged by their past failures or the callousness of online dating, and now they wanted to be on top, so to speak.

We lose so much when we reduce companionship to an adversarial proceeding.

Becoming partner at a law firm can be a matter of economic blackmail — you need to have a book of business you can take with you if you left the firm. In that way, the firm would rather make you a partner than lose your clients if you left. There’s usually some posturing that goes along as the associate attorney asserts their own importance and the firm pushes back.

But in real life, do we really want to cow people into being with us? The requisite skills include empathy and understanding, not rhetoric and persuasion.

I wish we thought of our dates as potential friends, and that we spoke to them as such, not as competitors or conquests or “others.” People we want to like, maybe even grow to love, and not just screw (on so many levels).

If someone cancelled on you for the third time, wouldn’t you think she didn’t care about seeing you? If you had an evening where your date asked you nothing about yourself, wouldn’t you think she was self-involved? Or if she ogled some fit, younger dudes, wouldn’t you feel diminished? (Yes, we can tell where you’re looking).

And if someone criticized your home or career or life choices, wouldn’t you want to escape them, especially if they were trying to sleep with you. We might outwit our dates, but we’re also precluding the possibility of love.

One of the best qualities we can offer somone is to help them feel good about themselves. And that means respecting their choices instead of crowing about how we could do better. Love doesn’t care whether you’re on the partnership track, only that you care for someone instead of trying to one-up them.