2016: Kelly Rohrbach

Kelly Rohrbach, a Sports Illustrated model, had one of Leo’s most meme-worthy flings. The two were photographed biking all over New York City, looking like a rom-com in motion. But it didn’t last — apparently, their busy schedules got in the way. Still, sources insisted it ended on friendly terms.

2016–2017: Nina Agdal

Danish model Nina Agdal was up next, and their relationship lasted about a year. There were vacations, paparazzi shots, and the usual whirlwind. When it ended, the word “amicable” popped up again — Leo’s favorite breakup adjective, apparently.

2017–2022: Camila Morrone

Now this was the game-changer. Camila Morrone dated Leo for nearly five years — practically a decade in DiCaprio time. They were serious enough that engagement rumors circulated, and Leo was said to be “very in love.” Camila even addressed the elephant in the room: their 23-year age gap, telling critics to judge the relationship itself instead of her birth certificate. When it ended in 2022, the internet immediately revived the “25 rule” meme — because, yep, she’d just hit that number.