96. Milo Ventimiglia and Alexis Bledel
Movie: Gilmore Girls
Location: Burbank, California
Year: 2002
Gilmore Girl fans remember the plotline between Rory Gilmore (Alexis Bledel) and her love interest, Jess Mariano (played by Milo Ventimiglia). On the show, the pair’s dating history was cut short by tons of drama. But, in real life, Bledel and Ventimiglia had a long relationship.
They began dating after they met on the set of the TV drama. They dated for four years, ending the relationship in 2006, right around the same time that the relationship went public. Fun fact: during Gilmore Girls’ run, Alexis Bledel dated three different co-stars from the show. Now, she’s married to Mad Men actor Vincent Kartheiser.
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