Leonardo DiCaprio has an infamous history of dating barely-of-age young women. It always spurs up some sort of tabloid frenzy, or more modernly, trending TikToks about who thinks what.

Age 50 and 19 are a somewhat extreme example of what I have seen as an increasing trend in my friends’ and my lives.

It’s a blurring of ethical lines and a battle of reassurance: “Well, I’m 19 … He’s 25 … I’m mature for my age … I’m legal.”

Reassurance doesn’t last forever, especially when patterns emerge that reveal something a little more sinister. Looking back on this reassurance, I regret my rose-colored glasses in ignoring what is a bigger issue that young women face.

It’s hard to even label it: Is it an age gap relationship if we’re only so-and-so years apart … both in our 20s?

When I was traumatically broken up with out of the blue on Thanksgiving, I had never felt anything like it. I felt small, young. Suddenly I was being told what to do, and what was going to happen, by an older man. 

And one of the first questions I asked him was: “Is it because I’m 21 and you’re 26?” 

Journalist Jill Filipovic puts it beautifully in one of her Substack posts:

“Men who serially date significantly younger women are not looking for equal partners. These men are indeed looking for someone who will admire them, who they can mold, and who will make them feel sophisticated and important.”

Jacqueline Bleadon, a former DePaul student, has also experienced a cycle of older men pursuing her. Bleadon’s first romantic experiences were with older men, which led to a tumultuous relationship with a 27-year-old when she was 19. 

“I just feel like the dumb 20-year-old who had this idea in my head about this guy that just was never gonna be true,” Bleadon said. 

For many months, I was molded to fit the expectations of someone older than me. I was told to stop drinking cheap vodka that came out of plastic bottles. I was told to use Apple Music instead of Spotify. I changed what music I listened to, what I ate, what I read and what I watched. I was convinced taking Kratom was cool and making beats was a full-time career. Funnily enough, none of these habits lasted longer than our relationship. 

Ironically, I was the one cooking dinner. Buying groceries. Paying my own bills. Answering the question of “which one is a Zionist again?” or clarifying that Italy was indeed a country, not a city. 

But I sure did admire him. I was his biggest cheerleader and supporter. 

Filipovic continues:

“Women in their early 20s who date (older) men aren’t children … but they are often taken in by the idea that there is something especially mature and unique about them that makes an older man choose them; in reality, the special and unique thing is that the older man needs an ego boost, not a partner.”

Why else would men 26-30 be sending likes to 19-year-olds on dating apps like Hinge?

Dalaney Stanford, a senior at DePaul, said that her initial attraction to older men who pursued her was that they were “mature, successful and had their life together,” until she realized that their older age didn’t actually signify more maturity, especially because of the younger women they go after.

I felt, for lack of a better word, cool, going around and telling my peers about how I was dating a 26-year-old or seeing a 30-year-old. I felt mature, “older for my age,” and a validation from what seems like a constant stream of older men pursuing me and other women my age. 

Bleadon and I have spent hours around my kitchen table talking about this topic. We retell our same stories over and over again in hopes of gaining some sort of clarity or explanation for this pattern.

We bring a similar sentiment to the table. We are independent and hardworking younger women who have been convinced that an older partner will be suitable for us.

“It just kept me going in this pattern of looking for older people because I felt that they were more mature, and the people my age couldn’t handle me and my independence,” Bleadon said. 

But the truth is that I was not there to be a partner, but as Filipovic puts it, an ego boost. 

Insecurity runs rampantly among men. Oftentimes, I see this insecurity being taken out on younger women. I have accomplished many things that I can say I’m proud of. I have excelled in my undergraduate journalism career and have many interests beyond school.

But what I am always asked is:

“How was school today?” It makes me seem like a second-grader, rather than a grown adult with agency and success who doesn’t need the guidance of an older figure. My achievements are consistently downplayed by older men who seem to be lacking in their own lives. Not to mention the disregard for my work at the DePaulia because of its association with “school.” 

Stanford has experienced being pursued by older men since she was a teenager. She said that she often feels talked down to by these men.

“You’re always going to be the younger, stupider one and I hate that,” she said. 

Why do I put myself in the position to have political arguments and be degraded by 30-year-olds who work at hardware stores? Why did I allow myself to be consumed by an unemployed, 26-year-old mommy’s boy? All while trying to navigate the tumultuous years of college and my early 20s–without my partner being able to understand at all. 

It’s their attraction to me that creates a nauseating, addicting validation that feels impossible to escape. Bleadon recalls older men giving her compliments and the extreme sense of validation it instilled in her. 

“There’s a reason it becomes a pattern,” Bleadon said. “There is a big difference between a guy who’s still mentally in his early adolescence, and a girl who has been with people a decade older than her … she’s seen some stuff.” 

Stanford said that this long pattern of engaging with men older than her has “conditioned” the way she thinks about relationships, along with believing that older guys are simply her “type.”

“Which isn’t right. I think that’s gross,” Stanford said.

I know my ramblings may make me seem bitter about getting my heart broken. But beyond this, what I keep seeing in my own relationships and with the horror stories from my friends, is a perfect display of the crushing patriarchy we live under as young women. 

We are expected to be the caretakers, the cooks, the cleaners while also being small enough to not appear better than our older counterparts. We are expected to understand the struggles of an older man while still upholding our young and innocent image.

And when the time comes, the original thing which attracted this man to us — our young age — is used against us to claim we were never mature, or good enough. 

“Damned if you do, damned if you don’t,” Simone De Beauvoir famously said. 

Even though Bleadon and I will probably continue to make mistakes in attempts to be “in a relationship that’s appropriate and won’t cause you insane baggage,” it’s okay. We are 21. We are learning. We still have the time to make mistakes. 

“I’m gonna be petty, I’m gonna say dumb things, and I’m gonna make dumb mistakes,” Bleadon said. “Because I am 21, I’m not the 30-year-old in this relationship. I’m allowed to make mistakes.”

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