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.

Now that Bobby has moved into Liz's parents' guesthouse, he's been warned that neatness counts – a lot! But his attempt to make coffee with Philip's fancy cappuccino machine leads to a burst pipe in the kitchen. In desperation he calls his dad, Mace, to help fix the calamity before Philip gets home.

When a client unexpectedly gives Philip tickets to a Red Sox game, Bobby sees it as an opportunity for family bonding and convinces Philip and Simon to invite Mace. But Mace's idea of how to watch a ballgame is quite different from Philip's and Simon's. Meanwhile, Liz tags along with the O'Neil women to a basement sale that's more like a battlefield.