Last week, an unofficial, silent alarm rang through the model community: Leonardo DiCaprio was single once again. The Academy Award-winning actor officially split from his 25 year-old model girlfriend, Nina Agdal, whom he first met in 2016 at an Oscars after party. Agdal is famously just the latest model ex for the perennial single actor, who over the years has dated a number of high-profile blonde glamazons, particularly of the Victoria’s Secret variety, including Gisele Bündchen, Toni Garrn, and Bar Rafaeli, to name a few. Curiously, only a handful of the genetically-blessed list have been publicly photographed together—most are just reduced to a blind gossip item or blurry iPhone pictures snapped by wannabe pedestrian paparazzi. Among those rumored, but unconfirmed girlfriends: Demi Moore, Blake Lively, Rihanna, Naomi Campbell, and Paris Hilton. Here, a look back at DiCaprio’s public outings with his significant others of the moment—none of whom, you may notice, were older than Agdal’s 25 at the time.