Plot

Earl tries to get Frank back together with his girlfriend after she breaks up with him, but he has second thoughts when he discovers that she'd be better off without him. Meanwhile Catalina gets a compromising cell phone photo of Joy.

On the prison's conjugal visit day, Earl (Jason Lee) is summoned to the hot box by his former roommate & would be partner in crime Frank (Michael Rapaport). Frank wants Earl to meet with his girlfriend Billie (Alyssa Milano) and explain why he cannot meet her. After Frank shows Earl a nude photo of Billie that reveals a tattoo in a very intimate spot, Earl goes to meet Billie. When Earl inadvertently mentions the tattoo and confesses Frank showed him the picture, Billie becomes angry and tells Earl he can inform Frank their relationship is over.

Meanwhile Catalina (Nadine Velazquez) takes an embarrassing photo of Joy (Jaime Pressly) with her cell phone. Catalina uses the photo to blackmail Joy to do her bidding. Joy is desperate and manages to get ahold of Catalina's phone and deletes the picture only to discover Catalina has already downloaded the picture and made copies.

To cheer up a depressed Frank, Earl lines up a date for Frank with Lucy (Fiona Gubelmann) from a website where women who want to meet prisoners post messages. Frank & Lucy seem to hit it off and head to the bedroom of the conjugal visit quarters leaving Earl alone with his date Annie (John Farley) who is a transexxual. After some uncomfortable moments, Earl and Annie discover they have some things in common and are having a freindly discussion when a scream comes from the bedroom. Bursting into the bedroom Earl discovers Frank is trying to make Lucy more like Billie by attempting to pierce her navel with a radio antenna. After rescuing Lucy, Earl agrees to help Frank win Billie back.

Joy decides the only way to stop Catalina is to make her a batch of poisoned cookies but decides at the last minute decides to use a laxative instead of poison. When the laxative takes effect while Catalina is dancing on stage, Joy is waiting in the bathroom to take photos of Catalina as she makes a mad dash to relieve herself. Catalina agrees to exchange the photos of Joy for the photos of herself.

With the help of Randy (Ethan Suplee) Earl rents a billboard with a nude picture of Frank and a message asking Billie to take him back. Billie agrees to meet with Frank on the next conjugal visit day. On the day of the visit Frank asks Earl to meet Billie while he goes to steal flowers from a dead inmate's memorial. While talking to her he learns that she had just graduated from community college on the day she met Frank. After Frank talked her into shopliffiting she abandoned her plans of going to nursing school and embarked on a life of crime with Frank. She tells Earl that inspired by his tale of the list giving him a second chance on life she has decided to go back to nursing school. But when she tells Earl she cannot continue to visit Frank while going to school and will wait for Frank to get out of prison before returning to nursing school, Earl realizes that he needs to convice Frank that Billie is better off without him.

Earl intercepts Frank outside the conjugal visit quarters and explains that as much as Frank's life is better with Billie, her life is better without him. Frank realizes that if he loves her he must let her go. He throws her nude photo in the trash and tells Earl that for the first time in his life he feels really good and decent. After Frank has walked away Earl pulls the picture out of the trash. He tears off the portion with her face and puts it in his pocket throwing the nude part back into the trash can much to the delight of the other prisoners who find it.