Agree to disagree

Widowhood, Feminist Men, and the Great Masculinity Compromise

Dating as a perimenopausal widow is its own flavor of complicated, but dating feminist men? That’s like trying to bake a soufflé with a recipe written in Latin or in my case Italian. Don’t get me wrong—I admire a man who respects women and doesn’t think “helping” means drying one dish. But sometimes, I wonder: is he truly feminist, or does he just see “masculinity” as a burdensome relic he’d rather not deal with?

Case in point: I once dated a guy who, after a couple of months insisted we split every check 50/50. It started as charming egalitarianism, but after the second vacation together , I began to suspect he wasn’t crusading for equality—he just didn’t want to pick up the tab.

The real conflict arises when the relationship starts to deepen. You see, I love being feminine. I enjoy wearing dresses that swish, heels that click, and lipstick in shades with names like “Scandalous Ruby.” But femininity shines brightest when paired with a proper masculine counterbalance. Not toxic masculinity—just a grounded, confident presence that complements, rather than competes with my energy. His masculinity was never in question until the time came to pay the bill, open a door, or send flowers for no reason other than to see me smile. Call me old-fashioned, but sometimes I like a little chivalry. So, here I am: navigating the dating world, appreciating feminist ideals, but secretly craving a partner who’s not afraid to take the lead and show masculine initiative like only a great man can.

Clinging to Femininity (and Your Sanity)

Here’s the thing no one tells you about being a widow in a foreign country: it’s lonely. There’s no handbook for juggling grief, hormonal imbalances, school meetings (in Italian no less), and the subtle art of applying eyeliner on my sagging eye skin. But there’s also something beautifully defiant about holding on to your femininity. It’s not about male approval. It’s about reclaiming yourself. Some days, that’s lipstick and a killer pair of boots tip tapping their way into a chic restaurant where my female friends are waiting for me, champagne in hand. Other days, it’s sweatpants and a double espresso with a Nutella filled croissant. Either way, it’s survival with a side of style.

And when my daughters see me, whether I’m dolled up for a date or eating ice cream out of the tub they’re learning that femininity is whatever you make it. And sometimes, femininity looks like shoving your bra into your purse because it’s cutting off your circulation. Thank god bra burning protests are a display of the past… my lingerie is just too expensive and beautiful to be treated in such a way.

The Secret Weapon—Humor

If you’ve ever navigated a foreign country’s bureaucracy while learning how to say ‘help, I’m overwhelmed’ in Italian, you know that laughter is your lifeline.

Like the time my date asked if I “saw marriage as a tool of masculine oppression.” My 14 year-old overheard and said, “Mom, you should ask if he saw showers as tools of personal hygiene.” I laughed so hard I spilled my wine.

Or the time I tried to explain to a neighbor why my kid was crying on the lawn. Turns out I had confused the word for “homework” with the word for “existential crisis.” Honestly, both were accurate.

Embracing the Chaos

At the end of the day, widowhood, motherhood, and dating feminist men are all about embracing the chaos. It’s about knowing that I am not perfect (but hopefully my eyeliner might be), laughing at the absurdity that comes from dating in 2024.

And as for the men? Well, if they’re bringing kombucha and man buns to the table, at least you can look forward to telling a riveting and hilarious story about how often you find your hair tie holding up his deliciously shiny locks. Because in this wild, wonderful, and ridiculous life, I’ve learned the most important lesson of all: sometimes, it’s not about the man. It’s about the wine, the laughter, and the joy of surviving another day.