Dealing with a 40-Year Age Gap: What It’s Like to Date Across the Generations

For most people, having a sexual or romantic relationship with someone way older or younger than you is awkward. You have to deal with differences in perspectives, differences in life goals, and sometimes physical differences—not to mention the odd looks and occasional condemnations you might attract from friends, family, and strangers. The not-always-unspoken question is, is this actual love? Or is it some kind of sugar daddy/momma relationship?

“Like any other relationship, some age-gap relationships can be healthy and some can be unhealthy, and there are plenty of shades of gray,” cautions professional sex therapist Vanessa Marin. “Of course, these can be tricky relationships since the partners are in such different life stages. One might be getting out of grad school, while the other is preparing for retirement. It can be hard to find enough to connect over, or shared goals to work towards.”

“You certainly do see a lot of powerful, wealthy, older men with young women on their arms, but that’s not to say that money is the sole motivation in all of these types of relationships,” she adds.

Another stereotype is that young women who date older men have daddy issues, or that these May-December romances involve an icky Oedipal component.

“It’s hard not to use our parents as barometers for measuring our adult relationships,” says Marin. “If you never had a solid mother or father figure, you could consciously or subconsciously seek out an older partner to fill that role. If your childhood was full of chaos, you might desire the stability of someone in a later stage in life.”

But people connect for all kinds of reasons, both sexual and emotional, and relationships can look a lot different from the outside than the inside. To learn more about the stigma and reality of age-gap relationships, I talked to some women and men who had lived them: Phil, an older man in a long-distance relationship with a 22-year-old; Dina, a kinky, polyamorous 20-year-old who goes to her older partner for life advice; Fiona, a 70-year-old who outlived her young husbands and dates men who will help her with the internet; and Brad, a 31-year-old who says older women are appealing because they get straight to the point. All names have been changed.

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Phil
69 Years Old
Oklahoma

VICE: Will you tell me a little bit about yourself?
Phil: I am a psychologist. I have an ongoing relationship with a 22-year-old woman in North Carolina. I spent two weeks with her last year, and we had a lot of sex.

How is dating young women different from dating men your own age?
It differs from women my own age because women my own age are filled with issues. Young women don’t have so many issues.

What’s your favorite thing about your girlfriend? What about her makes you happy?
Well, we are in a long-distance situation. I visited her for about two weeks and she visited me for about a week. She is exceptionally intelligent and creative. She sings opera; she writes poetry; she paints; she takes classes in Spanish and German. She is also very sexy. Her biggest quirk is that she sounds just like Marilyn Monroe—very young and “cute.” I love listening to her.

What is the sex like?
The sex is fantastic. I feel just like I’m 17 again. The only problem is that I can’t get nearly as hard as I used to, but I have a very well-trained tongue that she seems to love.

What does your family think of the relationship?
I haven’t told my family. I have a daughter who is 46 years old. It would creep her out.

Dina
20 Years Old
California

VICE: Will you tell me a little bit about yourself?
Dina: I’m a 20-year-old California-born Persian-American girl. I’m a second-year university student, love school and academia, love to read, love to paint, and have an inner goth side to me. I’m Pagan. I’ve been kink-aware since I was ten, and actively kinky when I started dating at 16. I came to [polyamory] after I turned 18. It was a few months before I turned 19 that I met my first older man who I came to love and have a relationship with, and that’s what made me understand age is a number and should not be an inherent barrier as the age gap widens.

One of your partners is 45 years older than you. How did you meet?
We met on Fetlife. He’s a retired member of the medical field, and I have a condition he was talking about in a forum thread there. We realized we had a good bit in common, met up one day for brunch at a restaurant… [then] discussed becoming play partners so we could both explore and gain experience with kinks we share, and it eventually turned into a romantic relationship, not just a friendship.

What is your favorite date you two have gone on?
It was a trip to Old Sac (Old Sacramento) one night just for the hell of it. We parked the bike and we went strolling around hand-in-hand, just enjoying the night air and the lights and sound. At one point we popped into one of the candy shops and he cracked up laughing because I was a total “kid in the candy store.” I was grinning as he found sweets he grew up with when he was a kid. Afterwards we came across a kite shop and he had to go inside. Through that I found out he ran a kite shop back in the day and still loves to fly kites when he can.

How is the relationship different than someone your own age?
It’s actually kind of the same. The biggest difference is that I can ask him for life experience-based advice that someone my own age wouldn’t have. Also, I get to hear stories about things I’ve only read about in history books. I love the intelligent conversations and gaining new points of view only he can offer because of the age gap. He’s made mistakes and decisions I haven’t faced yet, and can impart his insight based on his life for when I do face them.

The sex is different and awesome, too. He’s an amazing lover, took the time to learn my body, and uses every sweet spot he’s found and every trick he’s learned to make me scream and writhe in pleasure. Oral sex, in specific, is off the charts. Plus, with his age and a medical condition he has some amount of ED. He stays soft or half-hard a lot, and that means we can’t really do intercourse, but we don’t need it. That’s the plus of his knowledge and skill in the bedroom, and both of our willingness to experiment and try all sorts of new things.

What is your relationship with your father like? Do you think that has anything to do with a preference for older men?
My father and I are close. We have our animosities between us and some major philosophical differences, but he has always had my back as a dad. He’s stood by me through thick and thin. I don’t have “daddy issues,” though I’m not the biggest fan of who my dad is as a person sometimes.

Fiona
70 Years Old
Arizona

VICE: How would you describe yourself?
Fiona: I’m a sexually dominant, non-monogamous woman of 70. I’ve been active in the BDSM lifestyle in the UK, New England, and Chicago since the 1970s. I moved to Arizona to help with my arthritis, and it does help. That was a year ago. I have not made many local lifestyle connections in Arizona yet.

Will you tell me about your experience with younger men? What is the youngest you have dated?
All of my sexual experiences with men have been with men considerably younger than myself, including two marriages of 22 years and 14 years. The youngest men I have ever dated are currently in their late twenties. They’re here locally and I’ve been dating them for several months. Things have not progressed to intimacy yet…. I develop intimate relationships over a long period of time and very slowly. Former intimate friends with benefits from Vermont and other places visit me here.

What is the longest period time you have seen any of them?
The longest period of time was the 22-year marriage, which ended with his death. [He] died of a heart attack at 45.

How is it different from sleeping with or dating men your age?
I have never slept with a man any closer to my age than 12 years. I like the companionship, candor, and idealism of younger men.

Do they treat you well?
They treat me very well with respect and reverence and they are always anxious to be of service and very polite… I let them know early that I appreciate very old-school manners with a great deal of gender-based courtesy: opening doors, carrying everything that needs carrying, standing when I leave a table and rising when I return, conversing quietly with me and then ordering for me at a restaurant, etc.

Do they help you with things around the house, or boring stuff like that?
There have been sweet aspects of every relationship. My favorite dates are always dinner dates after an arts event, concert, or gallery show. They do household tasks and lately, internet research for me.

What is the sex like?
The sex is fantastic… infrequent, but exceptional. I prefer peak experiences, and for that reason sex only happens when I am the aggressor or more active partner. Sometimes I decide to do all of the “fucking” in the relationship… wearing a strap-on dildo and letting them know their part of the action is being pleasing and attractive to me. I only date and develop more intimate relationships with alpha males, though.

Do you think there is a double standard toward women when it comes to dating younger men? Why do people seem to think it’s more normal for the guy to be older?
I have no idea, but I agree that is true. I know there is a double standard when it comes to women dating younger men from experience. My relationships have and do attract attention. Comments of various kind come like, “Is this your son?” More comments from women than men. Some of these comments are curious and courteous, some are laden with envy or “wisdom”: Take my advice; it won’t end happy for you ; you will find you have nothing in common with this child .

Brad
31 Years Old
New Jersey

VICE: Will you tell me about your experience with older women?
Brad: I’ve been with a 62-year-old when I was 24. [We dated] for about two and a half years, on and off. She thought I wasn’t seriously attracted to her, until she found out I really was. I’ve been with older women who are younger than that, and many of them didn’t believe I was serious.

How would you convince them you were serious?
I would usually let a Freudian slip happen, something sexual, or maybe let age come up and insist it’s only a number. Also, I would just look them in their eye, and try to let them know.

What did you find sexy about them?
Their experience. They know and do things that are just amazing in bed. They also cut to the chase. They don’t play games.

So how is the sex?
Mind-blowing. Sometimes, in the beginning, you have to be a bit slower, they don’t always like the rough, young stuff. But when they do, there’s never enough.

How do you meet these women?
In person, usually. I’ve been fortunate enough to meet them on chance, strike a conversation, and spark interest enough for a phone number or email address.

How are they different than younger women or women your own age?
They know what they want. They expect certain things: dates on time, be a gentleman, call, be courteous, don’t depend on text. They don’t look for attention the same way. They will just say, “:et’s cuddle” rather than be whiny about it.

What is your earliest memory of being attracted to a much older woman?
Hard to pinpoint, but I once saw an older woman having sex through her window as a kid. Something just clicked once I started having sex.

What’s the favorite date you’ve been on with an older woman?
Favorite date? It was actually a simple one that didn’t lead to sex. I met her at a piano bar, and I listened to her talk, intently. I listened to her, gave minimal feedback, walked her to her car, and said how much fun I had. She looked me in the eye and kissed me on the cheek. I knew she felt the same from the kiss. It made me happy to make her happy.

What advice would you give for someone else who wants to date a woman in the 60-plus bracket?
Don’t be sleazy. Don’t take the cougar route, assuming Stifler’s mom wants to bang you. Listen, hold conversation, show interest, and they melt in your hand. Also, don’t be shy in bed; whip it out and be confident.

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