Older men often date younger women, but everyone can benefit when the age gap is reversed

• Single Women Over 50 Dating
• Looking For Older Women To Date
• 50 Year Old Singles
• After 50 Dating Sites
• Single At 50

Looking at the 55 to 64-year-old age bracket, there was a 6 percent increase in the use of online dating profiles between 2013 to 2015. Many of the top online dating sites cater to people 50 and over who are looking for a long-term relationship — and some are totally free! Another, who’s even older, asked me to introduce him to my 36-year-old friend when he heard she wanted to become pregnant. My friend Anna recently set up her 52-year-old girlfriend with a man of 56. “They would have suited each other perfectly,” she said.

In college I studied Computer Science and forgot how to talk to women. There just weren’t any of them, anywhere (or if there were, they were in hiding). As the only straight woman within reach, I soon became the de facto dating consultant for my male friends, despite my waning expertise. They were even more eager to pick my brain on all things female when I started working as an engineer and data scientist at OkCupid, where I analyzed data from millions of daters to get a sense of the “correct” way to date for men, women, and everyone in between. But what I soon realized was that sometimes the best way to date is to go off script. So that’s what this column, Undressed, is about: gender, social norms, dating rules — and what happens when we break them.

When I was a junior in college, a woman called “The Princeton Mom” wrote into our school newspaper telling undergraduate women to “Find a husband on campus before you graduate.”

Single Women Over 50 Dating

“Forget about having it all, or not having it all, leaning in or leaning out,” she said. We had more important things to worry about, like the alarming decay rate of our attractiveness. If we graduated without a future husband in tow, the men in our class would forgo us for younger, dumber women. She advised we start the search as early into college as possible.

Um, I thought, petting my two-years-younger boyfriend. If he was sour over being stuck with a crusty upperclassman like me, he didn’t show it.

I almost forgot about the Princeton Mom until last month, when international headlines went nuts over the new French president elect and his wife. Brigitte Trogneux met Emmanuel Macron when he was 15 and she was his 39-year-old drama teacher, already married with three kids. Not my ideal meet cute, but whatever — and it made me wonder: is the old norm of older man with younger woman out?

I decided to find out by pulling data on OkCupid messaging between straight daters from 2013 to today — so I looked at over 10 million “successful” conversations, defined as convos that included at least at four messages back and forth with contact exchange. At first blush, things didn’t look so hot: 61% of conversations take place between an older man and a younger woman, and in almost half of them, the age gap is at least five years older. The older-woman-younger-man combo is significantly more rare (appearing in less than one-third of all conversations), and in only 12% of these is the woman at least five years older.

It appears this age gap is largely driven by dudes. Men start 80% of conversations on OkCupid, and they tend to message younger women. The older men get, the younger the women they message (relative to their own age).

Women, on the other hand, message and respond most often to men about their own age. Once they reach 35, women actually respond more often to younger guys. But because men are usually the conversation starters, the older-man-younger-woman paradigm prevails.

Alright, so maybe OkCupid en masse follows dating age conventions, but what about those women who want to flip the norm on its head? How difficult is it for them to date a younger man? Could it be that the age gap exists just because it’s default behavior — a standard that persists simply due to the fact that it hasn’t been adequately challenged?

What I found was kind of surprising. When men message women, women tend to respond most often to men around their own ages. But when women message men, they’re actually more likely to get a response from younger men than they are from older ones. A 40-year-old woman will have better luck messaging a 25-year-old man than a 55-year-old one, according to the data. And a 30-year-old man is more likely to respond to a message from a 50-year-old woman than a message from any other age group. When women make the first move, the age gap dating norm is reversed.

A 40-year-old woman will have better luck messaging a 25-year-old man (60% reply rate) than she would a 55-year-old one (36% reply rate).

I asked my friend Trevor, a 28-year-old mathematician, what he made of it. “Well to be honest,” said Trevor, “I usually go for older women.They have more interesting jobs and hobbies, and their profiles are just better… no stupid selfie-only profiles.”

Did that explain it? I wasn’t sure, but there’s data to support Trevor’s claim: millennial women write the shortest profiles on OkCupid; profile length increases with each year they pass 35. (Across all ages, straight women write shorter profiles than straight men.)

Looking For Older Women To Date

And then there are those 50-year-old women who really clean up with the 20-year-old dudes. To be fair, very few 50-year-old women (fewer than 1%) actually message men this young, but when they do, they kill it.I asked Cindy Gallop, 57-year-old founder of MakeLoveNotPorn.com who openly champions the benefits of women dating younger men, what she thought.

Cindy has been dating men in their 20s for the past 15 years. Even though her relationships usually start with sex, her number one criteria for choosing a guy is that “he must be a nice person.” Often these relationships transform into friendships that last for decades. “Yes, the sex is fantastic,” she tells me, but that’s just one of the reasons she dates younger. Working in tech, she sometimes feels she has more in common with 20-somethings than older men. And as someone with an extremely accomplished career in advertising and entrepreneurship, she enjoys acting as a mentor to guys who are just “pulling themselves up by the bootstraps.” Cindy explained that men her own age often have a problem with dating strong, powerful women who make more bank than they do. “Younger men can’t be competitive,” she says, “because we are in completely different life stages.”

50 Year Old Singles

When I spoke with women who message much younger men on OkCupid, most of them told me something similar. They’re usually looking for casual relationships with men with rockin’ bods, but also often mentioned that men their own ages can be oppressively controlling. As one member who calls herself “Mrs.Robinson” said, “Men my age can be bossy and authoritative. I have no desire to have a man telling how I should be conducting my life. A younger man wouldn’t dare.”

It’ll be a while before I date a guy 20 years younger than I am, since right now he’s only 3. But I have been on dates with guys some 10 years older, and my feelings are this: no matter how diplomatic and open-minded they are, they always have a little trouble taking life advice from a 23-year-old.

But that’s just me. And still, I’m glad to know that even if older-man-younger-woman is the norm, it’s a pretty easy rule to break. The odds are in your favor if you do.

After 50 Dating Sites

Written and researched by Dale Markowitz. Graphics by Hanna Kim.

Whether you’re looking to date younger or older or don’t have a preference, give it a go at OkCupid.

A growing number of singles are trying to navigate these online dating options, especially during the pandemic — where meeting in person is less likely and poses a risk of COVID-19 transmission. In fact, the number of dating app users in the U.S. was expected to reach 26.6 million in 2020, according to Business Insider, an 18.4 percent increase from 2019.

Fiona Bloom, 54, rejoined dating apps recently after worrying she might not find a significant other amid the coronavirus outbreak. “COVID-19 has wiped out my love life,” says the New York City resident.

Dating apps and sites run the gamut from free to paid, and many offer free versions but charge a fee for all the bells and whistles. Since the pandemic began, many of these apps have added enhanced communication options, including video chat, designed to address the fact that it's hard to meet in person.

Single At 50

There are apps for general audiences and those aimed at singles over 50, while others try to match daters who are religious or those in the LGBTQ+ community. Here's your guide to some of the options.