S1, E3: Tess is beginning to master some essential back waiter skills, but there is still one thing she struggles with: the three plate carry. She asks Will to help her practice after work, which leads to her first romantic encounter with a coworker. The next shift, Tess meets Serena, an alumna of the restaurant who married one of their wealthiest guests, Fred Benson. Serena and Simone were best friends until Serena chose to leave the restaurant and settle down. To Tess, Serena has the picture-perfect New York life. But Simone teaches Tess not to believe everything she sees.