He's one of the most coveted men on the planet - and at 41, he's never been married. That means he's racked up quite the little black book - filled with supermodels, A-list actresses, and probably a few girlfriends you've forgotten about over the years.
They only dated for a matter of months - but it was filled with international vacations and PDA. Blake was filming The Green Lantern with now-husband Ryan Reynolds, and - well - we all know how that ended.
Okay, we admit that the British actress didn't have a lot of competition in this category - everyone knows this gentleman prefers blondes. The relationship wasn't ever very serious, but the two were spotted out on dinner dates during one of Leo's many breaks from Bar Refaeli.