7 weeks to launch: Older men, younger me
When you’re young, you think you’re the exception. I was not.
Welcome to my book launch series, where I dive into a pervasive topic from my book each week leading up to pub date (08/12/25). This week, I’m talking about the years I spent dating older men and how I thought it made me more mature, when really, those relationships lacked love, trust, and intimacy. I was the balm to their ego, an object rather than a human.
PSST: Whether you’ve been reading my work for 1 day, a year, 10, or 17 years, I’m asking you to pre-order my book. If you’ve ever agreed with me, disagreed with me, or been moved by something I’ve shared—whether it was in the New York Times, on the Today show, here, or on one of the thousands of Instagram captions I wrote in the 2010s—pre-order my book. It makes a huge difference for visibility so more people can read, discover, and share it with loved ones. I know you’ll love it !!
The thing about dating older men
It wasn’t until I was in the final throes of editing my book that I realized I had a pattern. Older men. It started in high school, when, within the first chapter of my book, I was “picked” by the most popular guy in school, a junior. The pattern would continue well into my twenties.
As a high school freshman, hanging out with older boys granted me a level of respect that differentiated me from the other girls. Suddenly, I was invited to the cool senior parties because an older guy liked me. I absorbed the subliminal messages all around me—the way every girl in my school gave older guys all their time and attention. They put the older guys on pedestals because they drove, had more relaxed parents, and more “experience” (LOL…as in, what, going to prom once?).
After high school, I think my choice to date older men echoed that same impulse, only this time it was intensified by my desire to escape the uncertainty I associated with youth. I wanted to catapult myself into adulthood, to bypass the aimlessness and instability that so often come with being young.
Readers might surmise that going to a residential treatment center 1,300 miles away at age 17 forced me to face things other girls my age didn’t have to. When most girls focused on college applications, what to wear to prom, and who else had a crush on their crush, I was dealing with recovery work and the mental health system.
Zev, one of the first ex-boyfriends in my book, was sexually aggressive with me and very possessive. He was 29; I was 23. But at that age, those six years felt like a lifetime.
Zev was deeply ingrained in the downtown NY scene, and I was drawn to his version of New York, and together, we blended scenes: SoHo House, Art Basel, raves in Gowanus. We used a lot of drugs together and partied five nights a week. We were codependent and deeply unhappy, but we stayed in the relationship because we knew being alone would mean facing our individual demons.
Zev wanted to own me; I was his property. He controlled everyone I spoke to, but if I had a problem with him keeping in touch with an ex who still loved him, I was the “crazy insecure” one.
To Zev, I was just a pretty young thing. But I can’t write about the older guy/younger girl dynamic without stating what was in it for me. I liked what Zev brought to the table: trips to the Hamptons/Long Island; full rides to Coachella. He owned his apartment (which his father bought him) and had the kind of insider access I didn’t yet realize I could one day create for myself.
He was a typical cynical New York man: raised between the city and the suburbs with a level of ambition and competition that ate him alive. If someone on his “good side” climbed up in life, he’d leech onto them, thirsting for an opportunity. If it was someone he didn’t like (because they didn’t pander to him), he’d spend his days trashing them, calling them rats, mocking their success, and spiraling into fits of rage that would end with him punching a wall.
No favor he did was out of purity or kindness; everything was transactional. One night at dinner, after our (female) waitress walked away, he whispered in my ear, “I can tell what a girl’s vagina looks like just by looking at her lips.” Then he added that this girl probably had a vagina just like his ex’s. Yep, that’s in the book.
And yet, I stayed with him. Anytime I tried to break it off, he’d lure me back with apologies and promises to be better. But then, within days, he’d tell me I was “pretty but not model pretty”, that “people are just trying to fuck me in business and fuck me in the bedroom”, and that “this is just who I am. Take it or leave it. You’ll never find another man like me.”
And we all know why men go for younger women. Young women are easily moldable; they are beautiful objects; tantalizing to look at. For them, it’s sheer beauty and innocence. They’re pliable. They quite literally haven’t received the wrinkles of time.
And then we have the big ex of the book: my European ex. As I entered my late 20s, I found myself yet again dating an older man, and this time, a 40-year-old one named Evert. He was Swedish, freshly divorced with two children and a lot of money to blow on a younger girl. Porsches, Rolexes, weekly trips, 5-star hotels. Again, we were both insecure; I worried about my beauty fading, and he worried about money and status. There was no foundation; the love and trust were not there. We were so insecure about the only thing we could offer each other.
I’m not saying every older man who dates a younger woman has an experience like mine. But I can only write from my vantage point. And so in my case, dating older men truly was the cliché we all hear about. It was never a neutral experience for me; they wanted my youth and body; I wanted their security and access. I was old enough by legal standards and financially independent, yet I still found myself in those kinds of relationships. There was no true intimacy. No real love. Not the kind of love that I know and have today, the kind of love I know I’m worth.
When I see celebrities like Leonardo DiCaprio and Jake Gyllenhaal dating women decades younger and point it out, I’m always struck by how quickly people rush to defend the younger girl, calling her “fully developed” and capable of making her own decisions.
Take what Emily Ratajkowski says herself—she’s now divorced from the man she married at 27:
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When I was with the Evert, I scoffed at people who judged our age difference. They don’t understand it, I thought to myself. But now, I see it for what it was. Post-divorce, he wanted to feel desired, sexy, and youthful. It doesn’t take a philosopher to see that some men miss their own youth so much that a younger woman is the only way they can feel vital and hopeful again. It’s nothing more than a stretch for a thing of the past, something they can no longer experience themselves, so they must get it through someone else.
Women, on the other hand, may try to find youth again through Botox and surgery.
A therapist once told me that some men go for young women at the age they stopped developing. Meaning, if a guy stopped maturing at 19, he will forever be attracted to 19-year-olds.
After I broke up with Evert, I felt embarrassed for dating him. A 27-year-old LA influencer dating a rich older European man? I was so cliché. I remember meeting his ex-wife while visiting him once in Sweden. I always wondered what she thought of me. Maybe she rejected him during their marriage. Maybe he couldn’t grow up. Maybe he didn’t like how smart and sensible she was. Whatever the case, I certainly felt like the young, dumb girlfriend when I met her, and I didn’t like it. I didn’t like it all.
That’s the thing about youth. We don’t know what we don’t know yet. And nobody can tell us what to do. We must experience it for ourselves.
I’d love to hear what you think. Comments are open to all. And remember, if you liked this essay, you’ll love my book.
Love how you are promoting your book! You are doing such a great job at giving bites of it to entice without giving away the whole pie. Can't wait to read it.
This is giving me so much to think about. I also dated a lot of older men and never considered why. There was almost certainly a desire for security and certainty as I lacked my own sense of self and worth. Many of the relationships, if you could call them that, weren’t particularly healthy and I do regret some of them. One in particular stands out as pretty reckless and pre-frontal lobe. Then there are the ones that were fun in the moment and rather harmless and I refuse to regret. There were some big feels and I felt as wild and free and alive as I ever had in some of those. Maybe that’s something I should unpack because I’d love to feel some of that energy in my life today!