It's All Relative - Season 1 Episode 2 Truth and Consequences
Overview: When Liz observes Bobby encouraging a friend to lie in order to break up, she questions his sincerity in their own relationship. In order to prove that he's changed and that he really loves her, she challenges him to find all the women he's dumped in the past and tell the truth about the break-ups. But Liz's plan may backfire when Bobby reconnects with the seemingly "perfect" girl.