When Brody discovers Jenny never wants to get married it's a blow. When she says she doesn't like musicals, it's just salt in the wound. But if Brody can change Jenny's mind about musicals, maybe one day she can change her mind about marriage. Mansfield gets out of planning his daughter's wedding by pawning his wife (Emily Rutherfurd) off on Threepeat, only to feel he's missing out. Derrick convinces Harvard he's taking things too fast with Lindsay - too bad it wasn't before Harvard visited the tattoo parlour.

Brody's ex-girlfriend Heather returns as a partner in the company and Brody thinks he's falling behind. As a birthday gift, Jenny decides to help Brody cross something off his life goal list to cheer him up. Mansfield has the perfect island wedding planned for his daughter, until the island sinks. With Lindsay's help, his hunt for a new wedding destination sends the whole office to sin city. Harvard feels out of place in Las Vegas until he finds the wonderful world of craps. Threepeat instantly reverts to being Heather's assistant until he snaps and finally stands up for himself. Things take a turn when Jenny finds an 'engaging' package in Brody's suitcase.