LORELAI: Ugh, they totally just snuck that modelling thing in.
RORY: Hmm, my mom’s a model. Maybe you’ll get to date Leonardo DiCaprio now.
Leonardo DiCaprio (born 1974), award-winning actor, producer, and environmentalist, known for taking unusual roles, especially in biopics and period pieces. At this stage, DiCaprio had won critical acclaim for his role in the 1993 quirky coming of age film, What’s Eating Gilbert Grape, and become an international star after playing the male lead in the 1997 epic romance, Titanic, which became the highest-grossing film to that point.
In 1999, he began dating Brazilian model Gisele Bündchen (born 1980), a relationship which lasted until 2005; this is what Rory is thinking of [pictured]. It’s another of those celebrity references which have had real staying power, because DiCaprio went on to date a number of other models, and since 2017 has been in a relationship with Argentine-American model Camila Morrone (born 1997).