Brody's ex-girlfriend Heather (Anna Camp) 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.