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She kept her relationships private at the time, but apparently she dated so many people from the show, it became a running inside joke on set. You're not supposed to be with one another," he advised. Don't just take, take, take, take, take—give, give, give, give."(E! Meredith collects data to deliver the best content, services, and personalized digital ads.Shockingly enough, these days Ventimiglia is single, and he has never married, but he seems to be doing just fine with his career and has a practical outlook on love. Back in 2001, he was cast as Rory Gilmore's bad boy boyfriend, Jess Mariano, and soon after, he and Bledel started dating offscreen.In 2006, after three and a half years of dating, Ventimiglia and Bledel broke up.