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Sex + Relationships

I’m Not Ashamed to Say I Dated Someone Almost 15 Years Older Than Me

Dating someone older wasn’t out of the ordinary for me because in my household, it was normal.

My parents have a 13-year age difference, my grandpa married someone almost 20 years younger, and my siblings even dabbled in dating someone nearly a decade older than them. So you get the point — the expression “age is just a number” has truly been the philosophy of my family’s love life. I recently dated someone nearly 15 years older than me (13.5 to be exact), and let me tell you — it was an unexpected rollercoaster. 

The attraction of dating an older man was always something that I always wanted to explore. Although, I never had an attractive teacher to daydream about, Matthew Gray Gubler and Chris Pratt were always in the back of my mind. But this past summer, I met the older man of my fantasies. We met at work and I didn’t think much of him at first. I didn’t even know his real age for the first two months (I was honestly shocked when my coworker told me). But like every rom-com, a few glances and a couple inside jokes quickly turned into a spur-of-the-moment invitation for movies and drinks on a random Friday night. One date turned into five and in the booth of an English pub, he asked me to be his girlfriend. I’m sure you have questions, because who wouldn’t? So, let’s go down the list:

Was the age gap a problem?

To be honest, I didn’t notice the age difference at first. He wasn’t the typical almost-middle-aged man. He wanted to go explore all of the time, drink at parties thrown by his friends, and wanted to fool around in the corner of bars. As the stereotype dictates, he was more experienced. He knew the best places for any occasion, he ordered the best drinks and knew everyone from the bartenders to the owner. It was intoxicating. As a newly 21-year-old, it was the one-way ticket I needed to abandon jungle juice and late night runs to McDonald’s.

However, references consistently went over both of our heads. When you mentioned either Billie Eilish or any YouTuber to this man, he’d give you the most cartoonish, quizzical look. But the cool thing was that we’d teach each other about it. Now, I know way too much about classic ‘80s cinema and Dungeons and Dragons — don’t even.

What did our friends think?

My friends had mixed emotions, as to be expected when they heard the news that we made it official. The general consensus was “Why are you dating somebodies dad?” followed by a frightened follow-up, “Dear God, wait, is he actually someone’s dad?” 

His friends didn’t seem fazed. Which, for some reason, was just as jarring. Why are you not fazed that your 35-year-old best friend started dating a 21-year-old? His friends were incredibly intimidating, and so was his lifestyle. Because he knew all the best places in our city, he knew the people who ran them. His friends were well-established, worldly, and could buy a $16 drink without desperately refreshing their checking account. I felt like a child being chaperoned at one of my parent’s parties. 

How was the sex?

To put it bluntly, sex got old quickly. He knew his way around, don’t get me wrong, but it was just bland. It became almost routine: watch an episode of His Dark Materials, he goes down on me, I go down on him, have sex once with all of the lights awkwardly on, and then brush our teeth for bed. In every relationship, a routine settles in at some point — but it was abnormally quick with this one.

man and woman holding hands
Photo by Thomas Ward from Pexels

How was the dynamic? 

Now I don’t want to speak for every significant age-gapped relationship, but it all had to be on his terms. Stay over when he wanted, move forward in the relationship when he wanted, but for me? I brought up bringing over two shampoo bottles to his place, and it was the end of the world to him. It went along the lines of:

“Would it be cool if I brought some of my bathroom stuff? I’m here all the time, I’d just like to have some stuff for my hair.”

“Uh, it’s a small bathroom.”

Are you kidding me?

Truthfully, it felt like he was my superior. I sat down for noodles with my friend, Carlee, and she told me about how she went on a few lukewarm dates with someone eight years her senior, and she felt the exact same.

“As much as you try to deny it, there’s definitely a power-play there.”

How was the relationship compared to partners closer to your age?

We moved along pretty quickly. The “I love yous,” key swapping, and weekends together happened so quickly I got whiplash. A couple of months in and it felt like I was living at his place. I literally told one of my professors that I moved houses and that’s why I was so late all the time.

I was never relaxed. Compared to other relationships I’ve been in, I feel uneasy about if he’d leave me for another woman more experienced, more mature — someone who opts for riesling over moscato. I felt like I had to prove to him (and myself) that I could be just as stable as him. It was exhausting. At the end of the day, I lost myself in the relationship.

Dating an older man became my identifier. People knew me as the girl who’s dating someone nearly twice her age. It freaked people out, made them whisper and question if he was grooming me. He wasn’t. We were just a guy and a girl who fell in love. He just happened to see more of the 1990s than I did. Nevertheless, the identifier stuck to the relationship. And then afterward, I was known as the girl who used to date men twice her age. The last question you’re probably thinking is — would I do it again?

I’ve been thinking that a lot lately. While that became my identifier, I’m a woman — anything we do becomes an identifier for a various amount of things. There were so many spontaneous, loving, and silly moments with him. There were so many problems as well — just like any relationship. This particular relationship pushed me to grow and learn to be more secure in myself, especially when it ended. So, would I do it again? Hell yeah.

Contrary to popular belief, Delilah Gray is not a fan of the song “Hey There Delilah.” Delilah Gray is the Founder of the Gray Times, a blog dedicated to career advice, plant parenthood, and sharing life lessons. She fell in love with writing when she lived in New York. She started because she wanted to help people, and she felt she could do that best by writing about what was happening in the world.  She has worked with Her Campus, Tokyo Journal, Carnegie Mellon International Film Fest, Platform Women, Queen V, and Long Island Weekly. She enjoys painting trippy portraits, watching dark cartoons, hiking, and spending all of her disposable income on her plants. 
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