6 Women On What It’s Really Like To Date Much Older Men

Last week in The New York Times, Maynard recalled her brief affair with Catcher in the Rye author J.D. Salinger when he was 52 and she was an 18-year-old aspiring writer.

As Maynard tells it, the acclaimed author read an essay she wrote and then reached out to her, urging her “to leave college, come live with him (have babies, collaborate on plays we would perform together in London’s West End) and be (I truly believed this) his partner forever.”

Their love story was short-lived. Maynard gave up her scholarship at Yale and moved in with the famed author, but a mere seven months later, “Salinger put two $50 bills in my hand and instructed me to return to New Hampshire, clear my things out of his house and disappear,” she says.

After writing about the affair in a book published in 1998, Maynard was labeled a leech and an opportunist by the literary world. Twenty years later, she wonders if people would see things differently had she published her story today. Was there something predatory about Salinger seeking her out, she wonders ― and what power dynamics are at play when older men date much younger women?

“In the decades since I published my story about those days and their enduring effect on my life, I have received many letters from readers,” she says. “Some are from women with chillingly similar stories to share, of powerful older men who, when these women were very young, captured their exceedingly naïve trust, as well as their hearts, and altered the course of their lives.”

There are likely just as many happy May-December unions as there are disappointing ones, but with Maynard’s story in mind, we decided to ask other women who dated much older men when they were young to share how the relationships changed their lives. Looking back now, do they feel they were taken advantage of, and what — if any — regrets do they have about the love affairs? Here’s what they had to say.

Astrid, 33

“I was 19, he was in his early 30s. We were together for maybe six months. Despite the age difference, I was the one with the money and the car. I remember having to pick him up at work a lot. There was a definite power imbalance in the relationship. I felt helpless in the wake of this older man who knew so much about sex — or who at least pretended he did. He made me believe there was a certain way to have sex and that I needed to have sex with him whenever he pleased. I was afraid I would lose him if I didn’t comply, so I did. I think he saw that I was young, lonely and vulnerable, and he absolutely took advantage of all three of those things. His girlfriend before me was young, his girlfriend after me was young, and I think he deliberately targeted younger women because they lacked the experience and knowledge to realize he was sexually controlling and a bit of a deadbeat.”  

Shanna, 35

“When I was 11, my first boyfriend was 16. Part of our relationship was proximity (he was the older brother of my best friend), and part of it was that a relationship between an 11-year-old and a 16-year-old was not seen as inappropriate where I grew up. As a teen, I occasionally dated, flirted with, etc. men in their early 20s, and as a college student, I dated men in their 30s and 40s.

I think I’m an anomaly in that I have an extremely strong mother, so while she may not have been privy to the details of my personal relationships, there was always her voice in the back of my head telling me when something felt wrong. I never felt pressured to do anything I felt uncomfortable with.

Luckily, most of these relationships were casual. But I think there’s an inherent power imbalance in a relationship when one partner is significantly older. You’ve lived more, you’ve done more. What’s unfortunate is that part of the allure of the relationship is that the older partner makes the younger person feel like they are special because someone older finds them attractive. It’s insidious. When I look back on it, there’s this gleam in a guy’s eyes when he finds out you’re even younger than he thinks you are. You can see the wheels turning, and then the comments like ‘But you seem so mature’ start. It’s a way of flattering you and absolving themselves of possible guilt.” 

Anne, 22

“We were more of a sex-buddies couple. I was 19, and he was 42. I met my partner through a sugar baby site. I was beginning to come out to myself as gay and had an incredibly difficult time with it. So my thought process was that if I could find just one guy that could do it for me, I could at least call myself bisexual. There was certainly a power imbalance. But not the one you’d expect. He loved having a young woman to have fun with, but I was still trying to convince myself of my sexuality. Don’t get me wrong — he was a great shag, all things considered. But I still just didn’t get into the vibe all the time. I’d be distracted by the fact that he was a guy. I couldn’t just pretend it was a chick giving me head or a chick with a strap-on. That was a thing I’d been able to play pretend with for years.

He genuinely was a nice dude. He was respectful and let me lead whenever I showed signs that I needed to. He read the signals I wanted him to and respected my boundaries. I don’t regret it one bit. He taught me a lot about myself, even though we never really had heavy conversations. And he eventually became like a mental push for me to accept myself for who I am and to come out to my family.”

Melesana, 70

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