When it comes to relationships, Leonardo DiCaprio has a very clear type: model, hot, and significantly younger than him. This has been true for literally as long as we can remember, and it doesn’t look like he’s changing his ways anytime soon. Last weekend, he was seen leaving 1Oak New York at 5am holding hands with his ex-girlfriend Toni Garrn, who (you guessed it!) is a model. It definitely seems like things are back on between the two of them, because why else would you be holding hands and then getting in the car together at 5am? In case you’re wondering, Leo is 42 and Toni is 25, but age is just a number or whatever.
While we’re here, let’s take a walk down memory lane, and look at some of the highlights of Leo’s dating career. This could take a while.
1. Emma Bunton, aka “Baby Spice”
That’s right, way back in 1997 when you were a small child, Leo dated a real life Spice Girl. Emma is Baby Spice if you’re wondering, and apparently he didn’t wannabe her lover bad enough to stick around.
2. Helena Christensen
Helena was one of the big supermodels of the 1990s, and she was also one of the original Victoria’s Secret Angels. She’s also five years older than Leo, but apparently that didn’t disgust him in 1997. After that, she started dating the guy with the dead eyes from The Walking Dead, and he…fucked a bunch more models.
3. Amber Valletta
The year was 1998. Amber was another one of the major supermodels of the 90s. Leo reportedly saw her in a magazine and had his people call her people, which is the most romantic thing we’ve ever heard.
4. Bijou Phillips
Back in 1998, Leo dated 18-year-old Phillips, who had a famous dad or something and was trying to be an actress. It didn’t last, and she ended up marrying Hyde from That 70s Show, but she did credit Leo with helping her get a movie role.
5. Gisele Bündchen
This just makes us feel really fucking old. In 1999, when Tom Brady was still playing college football, Gisele and Leo started a relationship that would be on-again-off-again until 2005. In a really eloquent interview from 2009, Gisele said “we were just not meant to be girlfriend and boyfriend.” Deep shit, man.
6. Bar Refaeli
After Gisele was gone, Leo quickly moved on from a Brazilian Victoria’s Secret model to an Israeli Victoria’s Secret model. Tough transition. They were together from 2006 until 2011 (minus a six-month break in 2009), and we really thought she might be the one after she introduced him to the Israeli prime minister. But it wasn’t meant to be, and now Bar is married to an Israeli man.
7. Anne V.
We mentioned that Leo and Bar took a six-month break in 2009, and Leo spent that break on a beach with Anne V, a top model who also dated Adam Levine back in the day. Seriously, these guys shuffle models around like a deck of cards.
8. Blake Lively
We almost forgot about this, and we still can’t believe it really happened. In the six months they were together, they were spotted in Cannes, Italy, New York, LA, and Australia. Okay, maybe Blake was just in it for the frequent flyer miles.
9. Erin Heatherton
If you’re keeping score, Erin is the fifth Victoria’s Secret model on this list. Casual. Like Blake, Erin was busy traveling the whole time she was with Leo. They were seen together in Sydney, Mexico, Hawaii, LA, and New York in the year they were dating.
10. Toni Garrn
Remember her? Toni (yes, that’s really how her last name is spelled; I didn’t just sneeze on the keyboard) and Leo originally dated from May 2013 to December 2014, during which they took beach vacations in at least four different countries. In case you were wondering, this means Toni was 21 and Leo was 38, so I’m calling the police. Looks like old habits die hard, because they’re definitely not done with each other. Oh, and Toni is also a Victoria’s Secret model.
11. Kelly Rohrbach
In 2015, Leo ditched the VS models for a Sports Illustrated model, and they spent most of the summer hanging out together in New York. There was a rumor that he proposed to her, but that was obviously false because he is clearly never getting married.
We’ll be clear: We don’t know for sure that they dated, but it really looks like they did. He helped plan her birthday party in 2015, and they were later seen meeting up at a club. Let’s just say, Leo doesn’t seem like the kind of guy you meet at the club just to say hi and go your separate ways.
13. Nina Agdal
Before the reappearance of Toni Garrn, Leo’s latest model was Nina Agdal, who can proudly say that she’s done both Victoria’s Secret and Sports Illustrated. She also previously dated Adam Levine, because of course, but she and Leo broke it off in May.