Dating in your 20s is a wild ride. Dating in your 30s is... strategic. But dating in midlife? That’s a whole different game and honestly, no one gave us a manual.
When I first dipped my toe into dating after divorce at 40, with four kids and zero single mom friends, I thought, “Freedom!” That feeling lasted all of five minutes.
After a rebound relationship, a stowaway child hiding in the backseat of my date’s car (yes, really), and a realization that men on dating apps cannot take a decent photo to save their lives… I learned a few things. Spoiler: dating at this stage can either be a comedy show or a crash course in resilience. Sometimes both.
From Swiping to Starting a Movement
The early 2000s were the Wild West of online dating. I tried Match. I tried Soulmates. I got ghosted. I got bored. I got played. One guy actually said, “Women are like buses... they all come at once.” I told him to try a different route.
But in all the swiping and scrolling, I saw a gap a need for a more grounded way to meet real people. So I created The Otto Connection. Named after my grandson (because why not make it wholesome?), Otto isn’t about instant hookups or algorithms. It’s about chemistry. Real-life, eye-contact, “pass the olives” kind of connection.
It started with 18 friends and friends-of-friends in 2022. Now it’s grown hundreds of curious, fun, unattached humans gathering for art shows, quizzes, film nights, and yes, a few picnics.
So... What Actually Works in Midlife Dating?
Whether you’re fresh on the scene or deep into dating fatigue, here’s what I’ve learned:1. Don’t Date From Fear
Lonely? Sure. Desperate? Don’t be. That’s how you end up in a situationship with someone who says “let’s vibe” but means “I’m emotionally unavailable.”
2. Your Ex? Not Invited.
No one cares about your ex’s snoring, infidelity, or Star Wars obsession. If you're still angry, go to therapy not a date.
3. Be Honest About What You Want
Want fun? Say it. Want serious? Say it. Pretending gets exhausting real fast, and you’ll end up stuck in the wrong story.
4. Don’t Judge Based on First Impressions
That person who seemed awkward on Zoom? Might just be your favorite human after a second drink and a trivia round.
5. Kindness is the New Sexy
Forget six-packs and stilettos midlife dating is all about emotional abs: kindness, humor, and a good “how was your day?”
So... What Actually Works in Midlife Dating?
1. Don’t Date From Fear
Lonely? Sure. Desperate? Don’t be. That’s how you end up in a situationship with someone who says “let’s vibe” but means “I’m emotionally unavailable.”
2. Your Ex? Not Invited.
No one cares about your ex’s snoring, infidelity, or Star Wars obsession. If you're still angry, go to therapy not a date.
3. Be Honest About What You Want
Want fun? Say it. Want serious? Say it. Pretending gets exhausting real fast, and you’ll end up stuck in the wrong story.
4. Don’t Judge Based on First Impressions
That person who seemed awkward on Zoom? Might just be your favorite human after a second drink and a trivia round.
5. Kindness is the New Sexy
Forget six-packs and stilettos midlife dating is all about emotional abs: kindness, humor, and a good “how was your day?”
