Dating in the Wild: Age Gaps, Expectations & A Few Uncomfortable Questions

Here I am, smack in the middle of the dating world—where everyone gets to choose their criteria like customizing a latte. Religion or not? Tall or short? How far are you willing to travel for love? And the big one: how old is too old—or too young—for a potential partner?

Personally, I feel most comfortable with a five-year window on either side—five years older, five years younger. That’s my benchmark. But let’s be honest: if someone six years younger shows up and they’re hotter than hot, am I really going to say no? That would be nuts, right?

Still, this question keeps popping up:

How young is too young for women dating in their 40s or 50s? It’s a loaded question. Think about it—what would you do if you were living in a completely different culture with zero judgment? Just to be clear: I’m not talking about anything illegal. I mean two consenting adults looking to dive into a passionate, potentially meaningful May-September romance. (Look it up—it’s a thing. Though, traditionally, it’s younger women with older men. Go figure.)

It makes me wonder: are times finally changing, or have I just been out of the loop? Women like me are often labeled with terms like cougar or MILF—ridiculous, over-sexualized stereotypes that make us sound desperate. Newsflash: we’re not.

Men, I’m calling you out—most of you don’t think twice about dating younger women. Not judging, just genuinely curious about the double standard

As a mom to two young adult sons, I even asked them: “How would you feel if your friend walked into a bar with his 30-something girlfriend?” Their response? “It’d be weird… right now, but age matters less the older you get.” Fair point.

Culturally, we don’t see this story told much from the female perspective. One of the few movies that comes to mind is Adore with Naomi Watts and Robin Wright—two lifelong friends who fall in love with each other’s sons. It’s steamy, unsettling, and definitely pushes boundaries. Honestly, it gives me an eww feeling every time I think about it.

Then there’s The Graduate, with the iconic Mrs. Robinson seducing a very young Dustin Hoffman. Or Summer of ’42, where a grieving war widow (played by Jennifer O’Neill) sleeps with a teenage boy. Are these stories romantic? Creepy? Both? Where should the line be when it comes to love?

I know some of you are squirming—I’m just the messenger. This is hardly a new conversation, but for someone re-entering the dating scene, it’s all feeling very fresh and a bit overwhelming. I’m trying to keep my eyes wide open.

So, are we really a culture of “free love” now?

Are we embracing love wherever it finds us, or are there still unspoken rules about who we’re “supposed” to be with?

I’ve heard it all—from “That’s crazy” to “If you’re into each other, why not?” I’m not here to make a ruling. But these questions definitely make me think about what kind of partner I want moving forward.

LOL…me being me, I’ll probably stick to what I know best—someone close to my age, maybe just a little younger, and definitely young at heart.

LC

xo