2011: Blake Lively

In a surprise detour from models, Leo briefly dated actress Blake Lively. Their fling started during the Cannes Film Festival and ended within a few months. Sources blamed “distance and timing,” which seemed convenient since Blake quickly moved on to her now-husband, Ryan Reynolds.

2012: Erin Heatherton

Leo kept the Victoria’s Secret streak alive with Erin Heatherton, and for almost a year in 2012, they looked picture-perfect. Their breakup was refreshingly low on drama — by Hollywood standards, practically boring. Erin never bad-mouthed him afterward; in fact, she said she was happy, which pretty much tells us this was one of Leo’s rare “clean exits.”

2013: Toni Garrn

Next came German model Toni Garrn. They kept things mostly under wraps, but whispers of a breakup got louder after Leo was spotted leaving a Miami nightclub with about 20 women in tow. Whether that was the nail in the coffin or just tabloid flair, Toni didn’t stick around long after.