Millennials Dish on Dating Older

May-December romances are frequently misunderstood. When you’re dating someone older, people might assume that the dynamic of the relationship is unhealthy or fundamentally unequal.

The ‘gold digger’ stigma can also come into play, and suggests that people choose older partners solely for their money.

“It’s a time-honored tradition in Hollywood for older men to date younger women, and cougar couples have become all the rage as well,” the New York Daily News explained, in an introduction to a slideshow on the May-December relationship trope in the entertainment industry.

To learn more about what these relationships are really like, ATTN: reached out to four people who have dated someone older than themselves via email about their experiences and relationship advice.

Here are five tips for dating someone older than you.

1. Ignore the haters.

When your partner looks visibly older than you, people might get a little nasty.

Courtney Croft, a 26-year-old Nashville-based anthropologist married to a 40-year-old man, explained that while she and her partner didn’t encounter too many problems in their personal lives, other people didn’t always react well to their relationship.

“Most of the issues stemmed from other people’s initial negative reactions of us being together. It really weirded people out. I had some people flat out say it was gross that I was with someone so much older,” Croft said. “Or that certainly he had ill-intentions, because why else would a man his age be interested in someone so young? Now that we’ve been together for five years, that happens less frequently, but when he lets his beard grow out, which is gray, and we’re out in public together, we still get questioning looks from strangers.”

These stereotypes can also be internalized. Maya L., a 25-year-old writer who declined to give her last name, told ATTN: she had dated a 37-year-old man at 25, and a 29-year-old man when she was 22.

“I try to be open-minded, but sometimes you have to wonder why they’re at where they’re at. Is it weird they’re dating me (a child)?” she joked. “Is it weird they’ve been divorced, or weird that they’ve never been married?”

How One Guy Reminded Us What Sexy After 50 Really Means

Over 50 and freaking hot is not as rare as it seems.

Chuando Tan, an allegedly 51-year-old Singaporean photographer, is currently melting the Instagrams with his series of white-hot selfies. Tan boasts over 400,000 followers that enjoy feasting upon images of the former fashion model looking sexy after 50 in tuxedos as well as the occasional shirtless self-portrait.

He got us thinking about how appealing and rewarding the company of 40 and 50-somethings can really be. Of course, we all know the temptations of 21-year-old Tinder tots with their soft cheeks and baby faces, but let’s be real. There is a lot to be said for a lover who’s been around the block – and back.

So, if you think that youth equals hot, let us present the argument as to why seasoned is even sexier.

The first reason they’re sexy after 50? Practice makes perfect.

First, let’s do some basic math. Older guys make great lovers simply because they’ve been around for at least 20 years longer than pretty young things (or, as I call them, PYTs). They’ve benefitted from the communication and instruction of wives, girlfriends, and lovers and therefore have learned how to please a woman.

You can expect that an older guy will know how to find your clitoris, your G spot, and that he will have spent his fair share of time bringing a woman to climax. He’s met all sorts of vaginas and knows that they’re all different and that, when it comes to sex, there’s no such thing as one size fits all.

They know that time, childbirth, and environment changes a woman’s body. They have seen their fair share of cellulite and stretch marks and are more likely to view curves as adventures, while younger men are more likely to seek the Hollywood ideal of attractiveness.

Younger guys are just getting to know how their own equipment works and have only recently been introduced to the female anatomy in a real world setting. For the most part, their dating pool has been limited to gals their own age and probably have not been afforded the company of an experienced lover. Unless they have a Mrs. Robinson in their lives, most PYTs haven’t met someone who can share with them what works in the sack and what doesn’t.

Patience makes perfect.

hot older man on a yacht
Photo Credit: Gianluca Vacchi 

Let’s think outside the bedroom for a second. Older guys have had to compromise and negotiate through all sorts of circumstances with all sorts of people, even coworkers and family members. These experience make for a more compassionate, attentive and patient lover in all areas of life — including sex.

Younger guys are often in it for their own pleasure and have yet to realize how rewarding and sexy putting someone else’s needs first can be. We’re not calling them selfish; they just have yet to learn that a woman’s orgasm is as much about mental stimulation as it is physical. And that trust can be sexy.

Because of their experience, DILFs are patient with our bodies. They realize that the more giving they are in bed the hotter the experience. They know what turns themselves on and in many cases, that’s seeing you get off.

Perseverance makes perfect.

Silver foxes have experienced so much more in life than their younger counterparts. They’ve already dealt with many of life’s difficulties and obstacles, and understand that slow and steady wins the race.

Anything they’ve felt the need to prove to others or to themselves has already been accomplished, leaving them more time to think about pleasing their lovers. This equals confidence and we can all agree that confidence is sexy.

Young men are often still seeking stable ground, affirmation, and are just beginning to build their confidence. And the cockier they seem, the more likely that they’re incredibly insecure — baggage we don’t want dragged into the bedroom.

How can you find your fox?

After feasting our eyes on Tan for longer than we’d like to admit, we decided to dig a little and see who else we could unearth. Turns out there are plenty of silver and not so silver foxes out there on the interwebs. Mark Ruffalo, Jason Statham and Jamie Foxx are just a few of the celebrities with an Instagram presence who came screaming into this world 50 years ago, and they just keep hollering.

All of these guys are DNA proof that being sexy after 50 is possible, but this club isn’t just for the famous. Keep your eyes peeled and your mind open and you just might find one near you.

Interested in reading about the relationship between age and dating? Check out what millennials think about dating older, why women love to date in a different age bracket, and what mature men are really looking for beyond just looks.