The Biggest Problem with Middle-Aged Dating: Living in the Past by @DWeissWriter #dating #middleage #living
All dressed up for another date when I was still single. Note the funereal black mirroring the death of hope.

When I started dating at fifty after losing my George, my biggest surprise was that everyone was disillusioned. Most of the men I met weren’t expecting much beyond an empathy machine, One long single guy opened our date with, “I realized I so excited to meet you because you haven’t been divorced so you’re not broken like the rest of us.”

Um, no, I was widowed and in my own kind of fresh hell. But I wasn’t yet disillusioned. I’d had a long marriage to a good man to whom I’d still be married if he hadn’t died. I assumed the men I met were like me, perhaps sad and lonely, looking for love, hopeful they would find a good woman.

But they weren’t.

They acted as if they already knew nothing was going to work out. They were entrenched in their own lives and they had little to offer except weariness. Most implied I was going to have to change to suit them. No making the extra effort to come to my suburban town. They didn’t even seem to want sex so much as they demanded I listen to their woes.

I Wondered: Why the Undercurrent of Hostility?

I hadn’t even had the chance to mess up yet. But back then, I wasn’t speaking my mind. Then I finally realized. These guys were living in the past, stewing in their prior partners’ alleged faults. Which often looked a lot like exacting revenge.

Most men seemed to think they’d financed too much in the past. So I’d get a riff from some guy I’d just met on how expensive dating was and how his ex-girlfriend had cost him too much, and, oh yeah, he’d get me a coffee, but he didn’t want one for himself.

Or I’d be treated to a lament about how his much younger ( really hot) ex-girlfriend moved in with him prematurely and sure the sex was great (ewwww), but she didn’t pay any rent and now he’s done giving. Got it, he’s overextended and I should expect nothing but resentment.

The Word I Kept Hearing While Dating was “Pay”

They kept saying no one “paid enough.” Which I took to mean emotionally, but my dates described financially. Perhaps because men are generally more comfortable discussing monetary, rather than, emotional cost.

I used to wonder why so many of the guys I met didn’t ask me more questions about myself. At the end of our initial coffee dates, I knew their histories, familial, financial, sometimes sexual. But they didn’t know much of mine except the bare outlines that I was a prior lawyer from a long marriage. And I’d made sure to work in that I was a lawyer so they’d know I had a job other than a sounding board.

I finally realized they didn’t care who I was because they never saw me. They saw only the past women who’d disappointed them. And they weren’t about to let that happen again. Not the ex-wife who got the house and the dog, or the hottie who got him to pay for everything, nor the mature woman who didn’t do enough for him.

I’d hear these men’s stories and I wondered, what’s the women’s side? I’d guess the guy vilifying his ex-wife for being demanding during their marriage was never emotionally present with her. Or I’d Imagine that the much younger woman he was complaining about started making reasonable demands of her own.

Or the last woman who dumped him got tired of his coming over and bringing nothing, not love or even a shred of empathy or even, perhaps, a dessert.

The Biggest Problem with Middle-Aged Dating: Living in the Past by @DWeissWriter #dating #middleage #living

Dating Felt Like an Exercise in Revenge

Whatever had happened in the past, these guys weren’t going to let it happen again and I better damn well know it. So they were super busy and I better be available on command. They offered coming to their house and hot tubbing as a second date. They picked expensive restaurants and ordered high-end wines without checking with me, mansplained over dinner, then said afterward oh yeah, we’re splitting this. It all felt like a power struggle.

But I was so polite back then. I‘d be pleasant, proffer my credit card when asked, and never see them again. They’d be surprised. But then, they never knew me.

I, too, became disillusioned. I started putting men in categories soon after meeting them. This guy is one of the “I’ve been fucked over by women” types. This man is one of the dog trainers who wants someone who jumps when he calls. This cowboy boot wearer is one of the aging playboys who wants easy sex but tries to make it sound like an exercise in personal growth.

One of the reasons I fell in love with my current partner is because he had a sense of wonder. He asked me lots of questions about myself. He read everything out there I’d written. He was so happy every time he saw me, like it was something he’d been really looking forward to. I was a brand new person, not the reincarnation of failures past.

As a practical matter, I weeded out people by making my dating profile very specific. I said explicitly that I wanted a long-term, monogamous relationship. I added that if someone was seeking something short-term or sexually adventurous, good for them, but I wouldn’t dream of wasting their time. I wanted to be too much trouble for most people. The revenge daters aren’t usually up for trying too hard.

I like to think we’re re-entering a world where we’ll realize how much we missed each other. We’ll better appreciate the chance for in-person connection.

No one is meeting new people in person these days. And we’re probably missing the types of connection that Zoom can’t offer. But maybe with more time alone, we can try to heal the wounds of disillusionment.

Re-emerging from our homes will bring with it a sense of newness. We might find love. We might be kinder to each other since we’re all coming from a place of shared vulnerability.

Having become more aware of our mortality, we might at least do better at limiting our time with the toxically jaded:

Thanks, I’m leaving now. No, I don’t want to hear about the fifth woman who trashed your faith in love.

Okay, gotta go. It’s been over an hour. I know all about your ex-wife’s spending habits, but you haven’t asked me one question about myself.

No, I don’t want to come over tonight. I just met you. That’s creepy.

Learn from my mistakes. If someone is spending your time explaining how he’s pissed off or devastated by other women, he’s probably not really with you. You deserve someone who’s present. And who loves this life. As we’re all learning, it’s more finite than we thought.




Connect with me on TwitterFacebook, Instagramor Medium, and be sure to sign up for my newsletter!

[gravityform id=”1″ title=”true” description=”true”]


Order My Book Here

Follow me

Are You Ready to Date After Your Loss?

Subscribe here to get a Free Checklist to your inbox!

(noscript) -->