Adventures in Midlife Dating
A few months ago, I wrote about normalizing not dating—and I meant it. But then I met a woman who told me how much fun she had dating all different people after joining Match. It sounded… intriguing. Meanwhile, I haven’t been on a date in 38 years. My ex-husband and I have been tangled in some weird codependent friendship for the past five years, hanging out weekly like some kind of post-divorce sitcom. We finally admitted how unhealthy it was and stopped a few months ago.
I’m not lonely. I go out every week to see a local Dead tribute band and know a ton of people. I have my book friends. And, honestly? I like being alone. But part of me felt like maybe I should at least try a few dates—just to officially close that chapter of my life.
So, I did it. I joined Match and Facebook Dating with the encouragement of my sister.
Dating Apps: A Second Job No One Warned Me About
Ladies, no one prepared me for this. Dating apps are a full-time job. The flood of likes and messages was overwhelming, but I wasn’t even remotely ready to go out, let alone give my number to a stranger. And let me tell you—men are impatient. If you don’t answer within seven hours, they lose their minds.
🗣️ “I guess you’re not into me. Bye.”
Dude. I was BUSY. I forgot to check the app. Also, slow your roll. Some of these guys were asking for my number within minutes of saying hi. My name is very unique, and a quick Google search basically hands over my life story. My name even shows up on caller ID. I wasn’t about to give that out to just anyone.
He’s a 9, But… He’s a Liar
Over the weekend, some bookish friends came over, and we played They’re a 10, But… You spin a number (1-10), pick a trait card, and see how that trait changes the rating. Example:
💔 “He’s a 9, but… he doesn’t cut his toenails. Ever.”
It was hilarious, but little did I know, I was about to live my own version of this game.
I matched with a guy who looked really familiar. His profile said:
✔️ 60 years old
✔️ Deadhead
✔️ New Yorker
✔️ CPA
✔️ Jewish (not a requirement, but nowadays it helps)
Tall, too. Which, let’s be honest, isn’t super common for Jewish men. Then he sent me a friend request on my real Facebook (my dating profile is under an assumed name, for obvious reasons), and we had 50 mutual friends. I accepted, but we never actually texted.
Then, he messaged me on the dating app:
🗣️ “You have great musical taste.”
I responded:
🗣️ “We’re actually Facebook friends.”
Not sure if he even realized it was the same person. But it turns out he’s been seeing the same band for 30 years and even remembers my son! He also walked me to my car one night after a show. So, when he asked for my number, I gave it to him.
And he actually called me. (Who even does that anymore?!)
We talked for hours, and he checked every single box.
BUT.
🚨 He lied on his profile. 🚨
He’s 70. SEVENTY.
To be fair, he looks younger. But let’s be real: at this age, looking younger just means not looking actively deceased. And while women seem to be aging like fine wine, the men liking me on these apps? They all look like my dad. Are they all lying about their age?!
So… he was a 9, but he’s 70. What does that drop him down to? 🤔
Honestly, I do trust him. He’s part of my music scene, knows all my people, and, let’s be real—I could easily ruin his social life if he turned out to be shady. So, if he asks me out, I think I’ll say yes.
If for nothing else than to finally break my 38-year dating dry spell.
I’ll let you know how it goes. Stay tuned. 😬
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