Camila Morrone Debuts New Boyfriend Cole Bennett After Leonardo DiCaprio Breakup

How serious were Leo and Gisele Bündchen when they were together? Well, she is the only woman he’s dated to ever walk the red carpet with him at the Oscars.

Leo and Gisele dated on and off from 1999 through 2005, becoming one of Hollywood’s hottest and most private couples. But in 2005, the Brazilian supermodel made the decision to walk away. And then, in 2019, she finally opened up about the breakup, revealing she was struggling with panic attacks and knew she needed to change her lifestyle.

“No longer numbing myself with smoking, drinking and too much work, I was becoming more and more aware of things that I’d chosen not to look at,” she reflected to PORTER at the time. “Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes.”

But in the end, it all worked out. In 2009, Gisele married Tom Brady, with her becoming stepmom to his son Jack from his previous relationship with Bridget Moynahan and later welcoming kids Benjamin and Vivian. However, the runway star and the former quarterback divorced in 2022.

She’s since found love again, welcoming her first baby with Joaquim Valente in 2025. 

As for Leo, he moved onto another serious relationship…