Love Across the Generations: When Cupid Can’t Do Math

They say age is just a number—but people start whispering when they see a young woman with a silver-haired gentleman who probably remembers rotary phones, or a young man proudly taking a woman out to dinner whom everyone assumes is his mother. What’s really behind these relationships?

Ah, the classic May-December romance! The assumptions start flying when a young woman dates a man old enough to have taken his driver’s test in a car with no seatbelts or when a handsome young man is seen having dinner with a gray-haired lady and presumed to be a gigolo.

Young women sometimes say, “Older men just get me.” Translation? He listens, considers her feelings and is patient with her.  He’d never “ghost” her because he doesn’t even know what that means.

Does she like his financial stability? Probably. Dating a guy with a well-funded 401(k) is a bit different from dating one who’s still splitting rent with three college buddies. Who doesn’t like vacationing at a Four Seasons hotel or eating at a Michelin starred restaurant? Maybe she has to keep explaining to him how to use AI, but life consists of many tradeoffs.

Older men have experienced life and don’t get easily rattled over running out of oat milk. They don’t play games because they’re tired. Literally. It’s 8 p.m. and time for bed.

But what about younger men dating older women? When the roles are reversed, society has a LOT more opinions—because apparently, Leonardo DiCaprio dating 19-year-olds is fine, but the image of 78-year-old Cher out on a date with 38-year-old music executive Alexander Edwards? Scandalous!

It’s fairly obvious why an older woman might date a younger man. He’s hot, and I don’t mean that his internal body temperature is stratospherically high. It’s common knowledge that testosterone levels, which drive libido and sexual function, peak in a man at around 18-25 years of age. 

The allure for a young man dating an older woman is multifaceted. She doesn’t play coy-she knows what she wants and isn’t afraid to go after it. She’s not shy about paying for her own dinner and will offer to pay to go on a real vacation. No hostels for her.

She’s confident and isn’t afraid of wearing what she wants and doing what she likes. Younger men love this energy. They get tired of threading carefully not to injure fragile emotions. No games and no unnecessary fights.

At the end of the day, whether it’s an older man with a younger woman or an older woman with a younger man, the truth is simple: people like what they like. It’s not important as to the reason WHY.