But with the Oscar-winning actor, 45, still going strong with girlfriend Camila Morrone, 23, we can only assume that this ever-growing list of love interest may soon come to a close.
So, for old time's sake, here is a comprehensive history of every single person (read: model) that DiCaprio has dated—both the rumoured flings and confirmed relationships.
This supermodel was Leo's first public girlfriend back in 1994.
The pair reportedly had a fling in 1995.
Leo was spotted with the OG Victoria's Secret model at a number of parties in 1997 after her breakup with INXS frontman Michael Hutchence.
Rumoured to be 'The One That Got Away', Leo took this model to the Romeo + Juliet premiere in 1996, but the two had broken up by the time Titanic was released.
The two were spotted together in 1997.
Allegedly, the pair had a fling in 1998 after Leo saw a picture of her in a magazine and had his management track her down. Romantic?
Leo dated the Czech model for two months after meeting at The Man In The Iron Mask premiere in 1998.
The hotel heiress was rumoured to be hooking up with Leo in 2000 as they shared a similar circle of friends and were often out together.
One of Leo's longest relationships, he shacked up with the Brazilian supermodel between 2000 and 2005, and famously took her to the Oscars as his date.
Leo followed up his long-term relationship with Gisele with a second serious relationship, dating Bar from 2005 'til 2011.
He met the Sports Illustrated model at a party in Las Vegas, and they were known to be fairly on-and-off from the get-go.
Leo dated his first combo of Sports Illustrated and Victoria's Secret model in 2009, whilst he was on a break from Bar. Anne went on to date Maroon 5 frontman Adam Levine for two years.
Leo took a break from professional models to date (the still extremely beautiful) Blake Lively.
He and the actress enjoyed a whirlwind five-month-long romance in 2011 before they broke it off and Blake moved on to her (now) husband, Ryan Reynolds.
Back on the Victoria's Secret highway, Leo dated Erin for around a year between 2011 and 2012.
This Brazilian beauty queen confirmed she was dating Leo in October 2013, after meeting him in Cannes.
The German-born Victoria's Secret model dated Leo on the down-low for 18 months across 2013 and 2014.
These two dated back in 2015, after being spotted having a heavy PDA in New York City. Though it seemed pretty serious, Leo's relationship with the Baywatch star didn't last too long, with the two breaking up at the beginning of 2016.
Supposedly, Leo was dating the 21-year-old Sports Illustrated model from May 2016 before she squashed the rumours and said that they had hung out, but he never made a move on her.
The images floating around of the two sharing a kiss seemed to say otherwise, but who are we to say...
In August 2017 relationship rumours started swirling around Leo and this 23-year-old German Victoria's Secret model (but of course) after they were spotted having lunch together. However, the biggest excitement surrounding their relationship was that the world was in shock that he wasn't dating a blonde!
Another model—but one with an unusually youthful age of 19 at the time (which was a 23 year age gap). Leo was spotted leaving an L.A. club with this New Zealand youngster in October 2017.