Bobby and Liz break the news of their secret engagement to their families and each gets a less than warm response. In fact, Bobby's conversation with his folks ends with him moving into Liz's parents' guest house. Naturally, this doesn't thrill Philip and Simon, but at the risk of losing Liz completely, they agree to the situation temporarily until Bobby can work things out with his parents.

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.

Mace learns a lesson about stereotypes when he takes ill and is treated by a doctor who happens to be gay. Philip learns a similar lesson when his longtime friend and party planner, Joffrey, makes his own startling confession. Meanwhile, as their Halloween party approaches, Philip and Simon disagree about continuing their long-held traditions, and Liz wants to shed her "cute" image.