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Sex And Relationships

A man’s POV: Dating in my 40s vs. dating in my 20s


October 13, 2020

If you clicked into this story, you only want the juicy parts right? A male’s point of view of what it’s like dating in your 40’s.  You must be thinking it is all about younger girls, strip clubs, parties, boat parties, one-night stands and weekend benders.

Well. Hell no.

I know a lot of guys (and girls) who have been in a long-term relationship who use that as an excuse to “make up for lost time.” I get it. Let your hair down and have fun. Go explore other relationships. It is the only way to see what you are really after in a future partner. After all, you are not the same person you were when you found “your partner” the first time around.  And you don’t know what you like unless you try things out.

Similar to Robin’s post dating experiences, I had the same thought process: How do I get myself back out there. Do I download the dating apps? I do hear all the crazy tinder stories. Something that didn’t exist when I was in my 20s. You would think it sounds fun right? After 15 years of monogamy, what guy wouldn’t want to start playing the field and make up for lost time.

My mates and I would always joke, imagine being single now, knowing what you know now. We would laugh and joke about how awesome it would be. Then one day it happened. I was the guy. It blew everyone’s mind.

I, out of all my mates, was back on the market. The one guy who had the perfect pin-up marriage is now single. You know that Seinfeld Episode “The wait out” (it has a cameo by Debra Messing), where Elaine and Jerry joke about “waiting out their message.” Well my DM’s lit up! Direct messages that is. Girls started “sliding into my DM’s” as I discovered it was called.  So the word was out. But that was the result of a public message that was disseminated on Instagram. In contrast to Robin’s experience, my ex-wife and I decided to post our split on Instagram. It caused a landslide of inquiry.

Normally I am super private. I like being incognito and flying under the radar. I never have or would use a dating app.  Not because there is anything wrong with it, but because of Instagram, I haven’t had to…Instagram was like my Tinder.

“Hey, I heard the news, hope you’re ok”

“Hey, just checking on you, hope you’re good.”

Pretty innocent… but was it really?

To be honest, I feel women are all very calculating. Like I was fresh meat on the market. While I had no idea what I was doing or how to handle this, I did find the new found freedom to do whatever I wanted pretty amazing. But, it was such a strange feeling putting myself back out there as a single 40 year old dad.

And just like anyone, the first couple dates were awkward.  It felt super weird buying condoms again. I felt like an 18 year old boy sneakily buying condoms.  It was just so weird. Sex and Good wasn’t live yet.

You finally get your groove back. And as much as the allure of going crazy was there, being 40 at the time, and knowing what I know now, really does change your perspective. I recently started journaling. It helped me figure out what it was I really looking for. (P.S. This is the best man’s journal ever.) While in theory, it sounds amazing to be back on the dating scene, it’s much different dating now than in my 20s. Your perspective is much more evolved. And while I would have liked to have fun, I realized I was really looking for a partner. And for what it’s worth, here’s my take:

The 20 somethings: As a 40 year old man, this sounded interesting at first. But they just aren’t at the same life stage. They want to travel, are either still studying or working part time. They want to see the world before they settle down. They want to go to the party’s and festivals. They are unsure of what and where they wanted to be. They have so much learning to do. I get it. I was the same at that age. To be honest I felt I was way past this.

Then there is the early 30’s. Mostly, I found these women were looking for a husband and to start a family asap. But I have kids, do I want more kids? Do they want to be step-mom to mine, this was all a bit too much. And this was an even more complicated age group for me. Our life goals just weren’t aligned.  

Then I dated in the late 30’s. This women knew what she wanted and wanted it yesterday. Having just came out of a 15 year relationship, I didn’t want to feel rushed. And I just wasn’t ready.

To be brutally honest, I have never been on a date with anyone my own age.  I never thought I would date in my own age group. My ex-wife was 9 years younger than me. And the dates I had been on in my life, the girls were always younger. I know, you probably think I am an asshole now. But, dating in what I like to call, your “adult” years changes your perspective. A lot. Let’s be honest, in your 20s you are not really an adult. You are just starting to figure life out in your 30s.

After dating around and around, a chance and very random evening halfway across the world. I met a 40 year old single divorced woman. And no, I didn’t care that she was divorced. I didn’t care that she was 40. All I cared about was that we got along amazingly. How did I get so lucky? An ex that cheated on her with a much younger woman… well his fuck up is my gain. And I didn’t see it as damaged goods. As many women fear. And we didn’t meet through a dating app, we actually met the old fashioned way: Connection and conversation. Without even knowing it, I was following the four lessons of post divorce dating. And it worked out amazing.  

Photo credit: the classic and unparalleled 1989 American romantic comedy film written by Nora Ephron and directed by Rob Reiner. It stars Billy Crystal and as Harry and Meg Ryan as Sally. 

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