Adrian Grenier and Emily Caldwell
Entourage star Adrian Grenier bedded some pretty attractive women in his hit HBO series. Not surprisingly, he took this trend off-screen as well.
2000 - 2003: Rumored to have quietly dated model/actress Beau Garrett
2005 - 2007: Dated Sports Illustrated swimsuit model Melissa Keller
2009 - 2012/Present? Quietly dated model/photographer Emily Caldwell. So quietly, in fact, we’re unsure if the couple is still together.
Adrien’s also been linked to model and Bachelor Season 16 winner Courtney Robertson, though dates of the fling are unknown.