Alexis Bledel (Rory Gilmore) and Milo Ventimiglia [1] (Jess Mariano) famously played love interests on Gilmore Girls [2], but they also dated in real life. The two first met on set when Milo joined the cast in the Fall of 2001, and they struck up a romance a year later [3]. They secretly dated for four years and even discussed marriage together. "I think everybody who has been dating for more than a couple of years probably talks about it at some point," Alexis told People back in September 2005. "It's a fun thing for us to talk about, but that's it." While it's unclear what went wrong, the two eventually split [4] in July 2006, and Milo's rep confirmed the news to People in a statement, saying, "He is currently single."
Since then, Alexis has gone on to marry actor Vincent Kartheiser (they tied the knot in 2014), while Milo was previously linked to Hayden Panettiere [6] and is rumored to be dating Stella McCartney marketing coordinator [7] Kelly Egarian. The former couple seem to be on pretty good terms now, though, since they reprised their Gilmore Girls [8] roles for the Netflix reboot in 2016 [9].