My First Time is a column and podcast series exploring sexuality, gender, and kink with the wide-eyed curiosity of a virgin. We all know your "first time" is about a lot more than just popping your cherry. From experimenting with kink to just trying something new and wild, everyone experiences thousands of first times in the bedroom—that's how sex stays fun, right?
This week, we're talking to Amy Anderson about her experience of dating older men. You can catch My First Time on Acast, Google Play, Apple Podcasts, Stitcher, or wherever you get your podcasts.
I identify as bisexual, and I’ve always had a preference for older men in particular. My first boyfriend was four years older than me, and since then I’ve always dated men who were at least a decade older than me.
I met my current partner seven years ago, when I was 21 and he was 44. We started dating at 24 and 47, and I’m now 27 and he’s 50. I definitely have a type with guys—much older, long hair, and beards. When I met my partner I thought, Wow.
We were friends for years before we started dating, because we were both in relationships with other people. The first time we had sex we’d met up and spent the evening together and realized we’d both been in love with each other for a while and hadn’t acted on it. It wasn’t the best sex, because the first time with someone never is. There’s always that awkwardness and uncertainty. But it was really fun and playful and explorative: all of those great things. And it’s just got better since.
Broadly speaking, older men are less goal-oriented when it comes to sex. They’re less fixated on this narrative that we have of sex in our society. It’s not this idea that you kiss and get naked and then there’s oral and penetrative sex, and that’s it. The older guys I have sex with are less focused on getting to the penetrative sex point as soon as possible, and they’re less focused on orgasm having to be the goal at all times—because orgasms are great, but sometimes they don’t always happen. Older people have had the time to unpack all the societal stigma that is programmed into sex. They’re more accepting of their sexuality and desires, and confident about expressing them with a partner.
I think that specific view of sex is something that younger men have. It comes down to the messages we absorb in our society; the messages we’re surrounded by. I certainly grew up thinking that sex went a certain way and that it was a very specific thing, and if you deviated from that, you were doing it wrong. For example, I spent years feeling broken because I wasn’t coming from penetration alone. I think a lot of women share that experience.
There’s a lot of stigma that comes with dating someone who’s much older than you. [With] people who say “you’re just with him for the money,” I shut down immediately, because I’m more career-driven and the higher earner out of both of us. People will always judge you, whatever you do.
There’s also a lot of stigma directed at the older man. People assume he’s just a creep who wants to have sex with someone much younger. That’s actually true in some cases, though. People say to me, “Is it not creepy for an older guy to be with a much younger woman?” I reply: “It depends.” I am creeped out by older guys who exclusively date women under 25, because I think, Why? It feels like they’re just fetishizing youth, which isn’t something I’m comfortable with.
I like to date guys who like me for me, not for the age I am. That’s what I have with my partner now—he says, “I would have dated you at whatever age you were.” Dating someone who happens to be younger, as opposed to dating someone because they’re younger, is where the line is drawn between creepy and not creepy.
"I think about the future all the time. It’s hard, and it’s complicated."
You can tell if someone is creepy by looking at the person’s dating history—have they dated people from all over the age map? I dated a guy when I was 19 who was 35, and he’d always brag to his friends that he was sleeping with a 19-year-old. Now I realize that was wrong, because he was treating me as a trophy, not a person. Using a younger woman as a status symbol is a big red flag.
Navigating age and gendered power dynamics can be difficult in age-gap relationships. It’s often easy for the younger partner to fall into a subservient role. My partner and I are very careful that we discuss everything from an equal footing. But there are times where I have to check my own internalized stigma and not assume that I should do what he says because he’s older and male. He’s taught me a lot, and I’ve taught him a lot as well.
We have a lot of fun together. I don’t think I’m missing out on anything. We go on holiday; we go on trips; we go out together. I’m not into the standard things that 20-somethings are into—I don’t like going out clubbing, that’s never been my thing. We have enough in common to make it work. Aligning values and desires is what matters.
I think it’s important to acknowledge that age does impact our relationship. Most of the time, it’s small stuff—he’ll make a reference to a band from the 70s and I won’t know what the fuck he’s talking about. The harder stuff to navigate is power dynamics and the possibility of the eventual ill-health and death of the older partner.
I think about the future all the time. It’s hard, and it’s complicated. The scary thought is that there’s the possibility that I may be left alone some day. It’s impossible to completely find a way around that. Because life does things, and age does things, and people get older and die. My view on it is that I could meet someone my own age, and they could get cancer or be hit by a bus and die. Life is fragile and unpredictable. I have to believe that the possibility of what might happen in 20 or 30 years is no reason to not take the happiness that’s being offered to me now.