7 Things That Happen When You Start Dating An Older Man

A big age difference can be a big deal.

Dating An Older Man Cassie Lopez on Unsplash

This summer, I, at the tender age of 21, fell in love with a 37-year-old.

He, for his part, disputes this claim, and in the unlikely event that he ever reads this, would probably prefer I stick to terms like “dated" or “developed a crush on,” but more on that later.

In case you missed it, big age gaps are having a major cultural moment right now.

From the infamous yet surprisingly long-lived Scott Disick/Sofia Richie romance to Drake’s newfound habit of hanging out with teenagers, May-December romances are raising eyebrows all over Hollywood right now. But what do these relationships look like when you’re not a celebrity?


RELATED: Why Younger Women Date Older Men — And Can It Really Work?

When my last relationship ended, older friends and family members all said the same thing about my 22-year-old ex: “He’s so young. Guys that age just don’t know what they want yet.”


This was annoying advice, but it wasn’t anything I hadn’t heard before. People have held men to lower maturity standards for as long as I can remember. I’ve been told that “girls mature faster than boys” since elementary school. Naturally, this is a problematic stereotype on multiple levels, from its reinforcement of a gender binary to its biological essentialism and casual refusal to hold men responsible for their behavior. 

Then again, my own experience has seldom contradicted this nugget of conventional wisdom, so I figured hey, might as well give it a shot with a man who’s had a little more time to pickle. I adjusted my Tinder age range, capping it at 38 instead of 28, and decided to see what happened.

I met up with a few so-so men in their mid-thirties, but it didn’t take me long to connect with Ray, the 37-year-old I ended up spending the summer with.

RELATED: 8 Men Reveal What They Really Think Of 'Older' Women


Here are 7 things that happen when you date an older man — or at least 7 things that happened when I dated one.

1. You get to go on better dates.

Or, rather, you get to go on dates, period. I don’t know if it’s because cusp Gen X/Millennials came of age in a pre-Tinder, pre-Netflix-and-chill era, or if we can maybe all hope to one day grow into the wining and dining lifestyle, but dating an older guy was definitely an upgrade in that dating him actually involved, well, dates. Go figure. 

When he held doors open for me at Upper West Side restaurants and held my hand as I stumbled out of West Village bars, my dating life suddenly felt much more Carrie Bradshaw and much less college.

Moreover, there were none of the annoying bad dating habits that modern technology seems to have bred in the younger generation. There was no vaguely suggesting we hang out then just never texting me on the day of the tentative plans, no "U up?" texts at 2 a.m., no pointless back and forth about where we should go for dinner. He made plans and he stuck to them. It was mind blowing.


On our first date, he texted to confirm and got there early to get us a spot. When I walked into the bar, he had already ordered a cheese plate for us. It was the most competent thing I had ever witnessed a man do — a realization that led to some serious consideration of just how low I had set the bar for men and to what extent I can blame it on society.

2. You text less.

For as long as I’ve been dating, texting has been the religion of any relationship. How often you text is the barometer for your relationship status and any decrease in frequency, shift in emoji use, or perceived change in tone has always been immediate cause for panic. 

When I was seeing Ray, however, texting was never a big deal. We texted back and forth a few times a week to make plans or sometimes to chat about something specific, but our relationship wasn’t defined by a fixed schedule beginning and ending with obligatory good morning and goodnight texts. 

For someone who once used to earnestly believe having someone to constantly text was the main point of a relationship, this was initially a strange, daunting concept. And yet, I was surprisingly fine with it.


Turns out your life — and your relationship/situationship/casual but secretly not-so-casual fling — is a lot less stressful when you aren’t constantly waiting for a text and then obsessively mining each one for hidden subtext that he doesn’t like you anymore. 

RELATED: The Perks Of Dating An Older Man, By His Zodiac Sign

3. You try to use him for networking purposes.

Ray turned out to be an inarguably good-looking guy, but admittedly, the collection of mostly blurry, mostly distant group shots on his Tinder profile wasn’t what got him a first date. Rather, it was the brief Internet stalk that revealed his job. I was actually explicitly forbidden from ever mentioning his real name, position, or place of work in an article pretty early on, but let’s just say the name of the company he worked for is enough to wet the panties of any unpaid editorial intern in New York. Tinder is the new LinkedIn, ladies.

On our first date, I politely pretended to ask where he worked, but I copped to my Internet stalk a few drinks in and joked, but actually not-joked, that he should get me a job. You know, flirting.


To this day, I even have an unsent text drafted in my iPhone notes to the effect of “Heyyy so I know last time we saw each other I told you I loved you then cried myself to sleep in your bed, but is there any chance you’d be willing to pass my resume along to anyone in HR?”  

4. Nothing, really.

By and large, I was mostly just surprised by how normal everything felt. Ray and I clicked pretty immediately. We had plenty to talk about and lots in common. In fact, while I’ve often struggled to make conversation with men my own age, Ray and I were seldom at a loss for words. More often than not, we found ourselves cutting each other off because everything one of us said triggered a new thought in the other one’s head. 

From time to time, a friend would inevitably ask me, “But isn’t it weird?” And, the answer, truthfully, was no.


All things considered, dating Ray felt pretty effortless — considerably more so than most romantic interactions I’ve had with men my own age.

5. His bathroom is cleaner than yours.

When you’re a straight woman dating straight men in their early to mid-twenties, you’re almost guaranteed to be the clean one in the relationship. This has its pros and cons. Sure, you have to hang out with some dude in his pigsty of an apartment, but you also get the satisfaction of knowing you’re the one that has their life together while putting in relatively little effort to maintain that image. 

When you’re a college student dating an actual man with an actual apartment, however, the tables turn. We spent most of that summer at his place, a pristine Upper West Side apartment that I routinely littered with shed hair and lost earrings. The one time he ever came to my place — a.k.a., my dorm room — I scrubbed the place down for an hour and still couldn’t match his level of cleanliness.

“Don’t worry,” he reassured me, “'girl bathrooms are always messy.”


6. He infantilizes​ you.

Something I have yet to mention about my summer romance is that from the beginning, it could never have been anything more. I was an intern living in New York for the summer, and, though we rarely mentioned it, we both knew I’d be leaving in August. 

We both knew our romance had come with a built-in expiration date, but that didn’t stop me from trying to thwart it when the time came. On our last night together, I went for broke. I told him I had fallen in love with him and I wanted to see him again. While I was prepared for rejection, I was not prepared for him to try to talk me out of it.

“We don’t know each other well enough to be in love,” he dutifully informed me. He told me that love wasn’t what I thought it was. He brought out the old “I know you may think you feel a certain way,” and “You're so young, you don’t even know who you’re going to be three years from now, six years from now.” He even dropped the, “You’ll forget about me in a month.”

All summer, our age gap had been more or less negligible. But as soon as real emotions came into play, I suddenly turned into a girl with a crush who couldn’t even be trusted to properly identify her own feelings.


7. You infantilize yourself.

Naturally, I wanted to be angry at him. But the truth was, as much as I pretended not to notice our age difference, I definitely got a certain thrill from it.

Dating someone significantly older than me inevitably heightened my awareness of my own youth and its power. The reality is, we live in a youth-obsessed culture and those standards are particularly high for women. At 21, I am already sharply aware that my own youth, and the power and privilege that comes with it, is on the verge of beginning its steady decline.

We often accuse men dating younger women of trying to relive their youth, but maybe the younger women in question have some stake in the matter as well. Dating someone older exaggerated my youth, making me feel like I could preserve or extend it a little longer.

On our first date, I remember strolling out of the bar hand in hand, drunkenly admitting that "I date older men because I know that someday when I am 37, my 37-year-old husband is going to want to date 21-year-olds." 


From day one, there was definitely a part of me that clung to the illusion of eternal youth the age gap provided — probably the same part of me that’s currently sleeping with a 48-year-old.

RELATED: Why I Only Date Guys Twice My Age

Kayla Kibbe is a writer wrapping up her final semester at Connecticut College where she is an English major with a concentration in creative writing. She covers trending celebrity and entertainment news, love and relationships, and astrology.