Dating in Your Mid-to-Late 30s: Too Young for the Dads, Too Wise for the Sons

Dating in your mid-to-late 30s is… complicated. You’re young enough to date the son, but grown enough to date the dad—and somehow, neither one feels like the right fit.

Both age groups, oddly enough, share one trait: they’re afraid of “settling.” The younger guys are paralyzed by FOMO, clinging to the idea that if they commit now, they’ll miss out on someone “better.” The older ones? Many have been through marriages, divorces, and life lessons—and they’re too tired or jaded to put in the work again. So they retreat into casual comfort or stay emotionally unavailable, assuming the right person will just magically appear without effort.

But even more frustrating than the search itself is this: most people aren’t honest about what they actually want.

Too often, they say what they think you want to hear. Out of fear, out of selfishness, or maybe just the habit of trying to “win” people over. They perform. They pretend. They mirror your desires to keep you interested—only to pull away once it gets real.

I have the utmost respect for someone who can be upfront. Tell me you're just looking for a fling? Great. Tell me you're looking for a lifelong partner, marriage, kids, and forever? Awesome. Even if it’s not what I’m looking for, at least I know. And that’s the beauty of honesty—it gives both people the freedom to choose what aligns with them before time, energy, or feelings are wasted.

It’s not about being perfect. It’s about being present. Being honest. Being real.

I’m not afraid of effort. I’m not afraid of love. And I’m certainly not afraid to walk away from anything that asks me to water myself down just to be accepted.

So yes, dating in your 30s is weird. But I’m living my life—fully, openly, and without apology. And I still believe the right one will show up when it’s time… not because I chased or settled, but because I stayed true.

Just some food for thought.

-AG-