Dating in your 50s is… an experience. From instant intimacy demands to mansplaining my own life, the obstacle course is real.
At 51, I’ve mastered many of life’s challenges: navigating career shifts, building a fulfilling independent life, managing finances, and creating a home that reflects who I am. Yet nothing quite prepared me for the bizarre obstacle course that is dating in my 50s.
The three-hour mark
There seems to be an unwritten rule in the dating app universe. Match with a man between 40-48, and I can set my watch by it: within approximately three hours, the conversation will veer directly into intimate territory. Not subtly. Not gradually. With all the finesse of a freight train derailing.
We start with the conventional pleasantries: “What do you do for work?” “How long have you lived here?” “Do you enjoy reading?”
And then, as if following some secret playbook, the questions transform: “Bikini or swimsuit?” “Dominant or submissive?” “Where do you like to be kissed?”
I recently told one particularly persistent interrogator that I wasn’t comfortable with this line of questioning. His response? Radio silence. Apparently, my boundaries were deal-breakers. How dare I expect conversation about mutual interests before discussing bedroom preferences with a virtual stranger?
The “confession”
Then there’s my personal favourite: The Confession. This typically comes from the slightly younger crowd, the 43-46 bracket.
“I have a confession,” they write, their digital voice practically dropping to a whisper. “I’ve been checking out your photos.”
Am I supposed to swoon? Blush like a schoolgirl? Perhaps send a flirtatious emoji? I’m 51, not 15. Of course you looked at my photos—they’re literally there for that purpose. This isn’t a confession; it’s the basic functionality of dating apps.
I respond with a simple “okay” and watch as confusion ripples through their messages. The script has been disrupted. I failed to giggle and twirl my metaphorical hair.
The gaslight special
Then comes the “The Gaslight Special.” This occurs after I express a preference or opinion about something I enjoy.
“You just haven’t been with the right man,” they explain, kindly informing me that my five decades of life experience are invalid because they, a stranger from the internet, know my desires better than I do.
When I respond with, “I’m 51. I know my mind and what I’m talking about. What you’re doing is gaslighting,” the result is predictable: ghosted. Apparently, women who can identify manipulation tactics are terrifying.
An open letter to 40-something men on dating apps
Dear 40-something men on dating apps,
I have a revolutionary idea to share: Women in their 50s are fully formed human beings with interests, opinions, and life experiences. We know who we are, what we want, and what we look like.
Your “confessions” about looking at the photos I purposely uploaded don’t thrill me. The rapid pivot to intimate questions doesn’t intrigue me. Your assumptions about what I “really” want don’t impress me.
When I was 25, perhaps I would have blushed at your attention. At 51, I’ve earned the right to expect more. I’ve built a career, created a life I love, developed deep friendships, and weathered life’s storms.And yes, I’ve grown up and grown out of seeking any kind of validation through your approval of my physical appearance.
So here’s my question: When will you grow up too?
I understand that dating is challenging at any age. But surely, by 40+, we can aim higher than conversation that would feel immature in a college dorm room.
I’m still optimistic enough to believe that somewhere out there is a man who wants to know about my interests before my intimate preferences, who sees me as a whole person rather than an opportunity for conquest, who understands that mutual respect is the foundation of any relationship worth having.
Until then, I’ll continue navigating this bizarre obstacle course, armed with boundaries, self-respect, and an increasingly absurd collection of conversation screenshots that my friends refuse to believe are real.
Because dating in your 50s isn’t just about finding someone—it’s about maintaining your sanity while doing so.
