Karen's cold feet about marrying Freddy (Daniel Cosgrove) cause drama as her wedding day arrives, and Lisa suspects that Nick is the reason why. Brian Jr.'s (Will Shadley) mother returns after her two-month Brazilian getaway to reclaim her son, to whom Brian Sr. is now attached. As Patrick's senatorial campaign heats up, his wife finds out about his extramarital affair from an unlikely source. Meanwhile, Natalie Kimpton (Tamara Feldman), who has stolen Juliet's bangs as well as her brother, tries to mend fences with Juliet by releasing a pop song with lyrics about forgiveness -- but a distrustful Jeremy thinks Natalie is pulling a con.
A high-stakes poker game on a yacht -- $20 million just to get in -- pits Simon Elder against Tripp, and the wagers are some of Manhattan's most sought-after properties. If Nick can convince Tripp to bet his most prized property, Elder will give Nick the dirt on his father's death. Karen panics when she learns she can't marry her fourth husband until her last divorce from the wildly irresistible Sebastian Fleet (Eddie Cibrian) is finalized. Meanwhile, Juliet introduces Brian Jr. (Will Shadley) to the joys of materialism, a blackmailer takes photos of Patrick and Carmelita, and Jeremy starts working for Tripp as a parking lot attendant -- but is distracted by a mysterious beauty (Sof质a Vergara).