Yes, he dated this model.
They were together 2013-2014. That's them on a yacht, because of course.
They were on and off from about 2006-2009 and then 2010-2011. This is them on yacht too. Leo likes yachts.
In 2009. That's not a picture of them dating, but that *is* a photo of when she was with Adam Levine and they are saying hi to Leo at a basketball game. Maybe they made a deep connection there.
They were together for 8-ish months in 2015. Here they are at a sporting/vaping event.
Yah, they dated.
From 2000-2005! They were so legit they made red carpet appearances together.
They were together for a little bit in 2012. Those who bike together, stay together (for only a short amount of time though).
'Twas a fling, but it happened in 1998. It was so lowkey though that there were no pics of it even happening, so this is my reimagining of the relationship.
They are dating NOW. Like, right as we speak!! Here are some creepshots of them buying bagels in Montauk, NY.