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Lip and Ian spend the night in jail on grand theft auto charges. Lip tries to take the blame so that it won't prevent Ian enlisting in the Marines. Fiona tries to locate Steve while waiting in the police station; Debbie hastily visits Steve/Jimmy's mother and tells her the truth; Frank tries to foolishly manipulate Karen to keep recent history a secret, which pushes her off the edge; Fiona tries to find out the truth of the stolen car from Ian, who also admit to being gay; Frank over and over narcissistically tries to justify his sleeping with Karen in front of the bar patrons, and tries to lecture to his audience, even going as far as using profanities about Ethel and Kev's relationship in front of Kev; Steve offers Tony the house he bought; while Karen is having depression, Lip visits her and in a passionate moment tells her that he loves her, which results in a breakup; Eddie finds out that Frank slept with Karen and goes in search of revenge, which makes Frank a homeless fugitive later, joined by Lip, which then turns into a violent showdown until Kev comes and stops Lip. Fiona has a difficult decision to make when Steve asks her to run away with him to Costa Rica. Frank tries to justify it about not having money and starts steering the conversation towards Sheila's money. Broken about past events, Eddie Jackson digs up a big ice fishing hole, ties a cement block to his feet, and jumps in the frozen lake; Lip and Karen make up; Fiona initially decides to go with Steve, but then changes her mind.

Frank is in line for some settlement money but there's a catch: he needs a woman named "Monica" to sign the paperwork, and there may be more to Monica than meets the eye. Debbie discovers a secret about Steve, and extorts him to keep it a secret. Ian has an eventful day at work, and Lip does some work for Steve to buy concert tickets for Karen.

Cathy, Marlene, and Rebecca have lunch at a ladies' club. Cathy learns of Marlene's Alzheimer's and considers bee sting therapy to cure her cancer.

Will's return to the Upper East Side continues to stir up problems for Serena, Lily and his long-standing rival, Rufus. Serena and Jenny's relationship is strained as a result of Jenny's deception. Blair spends time on the Columbia campus and realizes where she truly belongs. Dan learns that Vanessa has been keeping yet another secret from him, and Chuck struggles with the idea of Lily's sickness.

Vince gets a taste of the fashion world when he agrees to do a Dolce & Gabbana photo shoot with a supermodel. Ari pays his respects at a funeral, and winds up getting offered the chance to head the movie studio Warner Bros.