Jon Hamm has made a career out of playing men who are very comfortable having casual hookups, from Don Draper to Ted in Bridesmaids. But in a recent interview with Elle, the actor admitted that his very first sexual encounter was far from suave. When asked what he'd change about losing his virginity, Hamm replied with a laugh, "I don't know. Everything? There's no version of it that's not awkward. Let's put it this way: As much as I had practiced, I was still not quite ready for game time." Let's ignore his use of the phrase "game time" for a moment and consider how this man who embodied the quintessential Manhattan playboy could have been so awkward in his youth. Hamm lost his virginity at 19. The actor didn't make his first appearance on screen, however, until he was 26 (when he was appropriately billed as "Gorgeous Guy at Bar"). By the time he hit Mad Man fame, he was in his late 30s. Maybe, like most people, his ease with knocking boots increased with age. Or maybe, as is the case with so many talented actors, Hamm's on-screen persona is just dramatically different than he is in real life.