"I'm the Older Woman and Being With a Younger Man is Not What I Expected" Would The Age Gap Matter?

Kelly E.

Were the younger guys just checking off a MILF fantasy?


We were sitting at a table near the bar, listening to a local band, when two beautiful women approached us. They clearly knew Ben and both gave him a hug.

“Who’s this?” they asked, eyeing me up in their tiny, figure-hugging dresses and expertly applied makeup. At 39, in jeans and a “going out” top, I suddenly felt over-age and under-dressed. “Is she your girlfriend?”

“No, we’re just friends,” said Ben.

In that moment, I felt something shift. I’d never thought of Ben as anything more than a friend — he was almost 12 years younger. Why was I now wishing the answer was “yes, she is.”

Making Assumptions

I’d known Ben and his family for a few years. He’d mentioned having a bit of a crush on me, but I didn’t think much of it. Like many women, I had assumptions about younger men and believed quite a few age-gap myths. One was they wouldn’t be interested in a 39 year old divorcee. Why would they? There are so many gorgeous younger women to choose from!

Like many women, I had assumptions about younger men and believed quite a few age-gap myths.

Ben was just a friend, and after my 15 year marriage ended I needed friends around. So I invited him to hear a local band play. Both single, we joked about being each other’s wing-man at the concert. Ben hadn’t had a serious relationship for a few years. I wanted to see him with a girl who was a potential keeper this time: someone kind, smart, confident, stable, and fun.

At the concert I scanned the room and picked out girls I thought might be suitable. I talked with a few, but none of them seemed like a good match for my friend.

At the end of the night, Ben called me over to the back of the bar where he’d spotted an old piano. He patted the stool for me to sit next to him. Our arms pressed against each other, he played quietly — just for me.

“Here’s a man I could fall in love with,” I thought, surprising myself.

As he walked me home, Ben shook with nerves. I felt heat rise into my face. “Won’t it be like kissing my brother?” I wondered.

It wasn’t.

Holding me in his arms, I could feel he was still shaking slightly. “I didn’t think a woman like you would be interested in me,” he said.

Clearly, both our assumptions were wrong.

Breaking Stereotypes

After my marriage ended, I was invited on dates by a couple of men in their twenties. It was a shock to me that men 10–15 years younger would be interested. After having a couple of lovely dates, I asked another guy friend for his thoughts.

“Is it just the MILF thing, do you think?” I questioned him. “I can’t figure out if they’re just ticking off some fantasy.”

“MILFs and cougars are characters,” he said. “They’re not real people. No-one should ever think of real women like that.” He knew some of the guys who’d asked me out and reassured me. “They asked you out because of who you are.”

It’s pretty obvious if a guy is into you or just ticking off a fantasy. When one guy used the term MILF within the first hour of talking to me, I knew exactly why he was asking me out and he didn’t get the answer he was hoping for!

It’s pretty obvious if a guy is into you or just ticking off a fantasy.

Fresh out of a failed marriage, I wasn’t ready for anything serious yet, so — out of curiosity — I started asking my dates why they weren’t taking younger girls out. “I’ve found younger women have quite a few unrealistic expectations,” one of them told me. “Most of the girls I’ve dated in their early 20’s had self esteem issues and were pretty demanding.” Other guys made similar comments. This felt like a bit of a generalization to me, I know a number of confident, lovely women in their 20’s, but that was their experience.

As an older woman, I came to realize that I had a lot more to offer than I thought. I’m comfortable in my own skin, have my own established career, interests, and friends. I know myself, and certainly understand men and relationships more than I did in my 20’s! All of these things were quite attractive to the guys I was meeting.

What will people think

A few months after our first kiss, Ben and I started wondering if we could be something more. We’d been seeing each other every week, talking every day, and going on dates, but we still thought of ourselves as mostly just friends.

I’d come to terms with the 12 year age gap — I knew others in relationships with bigger age gaps — but Ben struggled to get his head around it.

“I feel like a boy next to you sometimes,” he said. “You’ve owned homes, raised a family, had more life experiences…”

Other people shared their concerns too. For them, being older was less of an issue than we expected it to be, but some family and friends were worried that Ben was just my rebound guy. Could an older divorcee really want to be with this young guy long term? Or would I break his heart?

More than a rebound

Ben was the emotionally mature, kind, gentle, creative man I’d been looking for. I knew he wasn’t just a rebound.

As we got closer to our one year anniversary, I noticed a change. Our friends and family had completely accepted us and I’d been invited to big family events. Everyone could see this was the real thing. No-one even mentioned the age gap!

Our love was changing from just attraction to something deeper. Every now and then he’d stare into my eyes and my heart would skip. “Is he going to propose right now?” I’d think.

On my birthday, sitting on the edge of Mount Eden volcano in Auckland, he did. A few months ago, I married the younger man I never expected to fall in love with!

I had assumptions about dating people who weren’t my age. We think we’ll be most compatible with others raised in the same generation as us: you’ll like the same things, share similar experiences, be raised with similar mindsets.

The reality is, compatibility is more about your personality than your experiences. In adulthood, age has very little to do with how well you’ll get along with someone else. We’re not stuck in classrooms with our same-aged peers anymore!

Age-gap myths are just that, myths. Why not widen your dating range by a couple of years? You might be surprised.

Photo by Remy_Loz on Unsplash

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