While attending a New York film society function, George introduces Jonathan to a filmmaker, who asks him to rewrite a screenplay. Later, he goes out with a party girl and leaves the script at her home, which happens to be a shrink's office. Jonathan asks Ray to pose as a patient to recover the script. Meanwhile, George encounters his ex-wife and her smug new husband.

Having picked up the gauntlet thrown down by Richard – and having thwarted a blackmail bid aimed at getting Jonathan to take a dive – the Edition team gear up for a tripleheader boxing challenge against their GQ rivals. But with the bouts only hours away, the women in their lives offer some compelling reasons why winning isn’t everything.

Jonathan is hired by Richard Antrem, George's nemesis and boxing foe, to investigate Richard's suspicions that his wife Priscilla, George's ex, is having an affair. Jonathan's insecurities resurface when Stella announces she's not over her first love. George has a new female urologist; Ray plots to win back Leah by penning a comic book.

Leah hires Jonathan to help find her new dog, “Little Ray.” Ray joins Jonathan in the search for the dog, getting some inside help. A reflective George heads to the hospital for surgery.