No day is more special to a prisoner than Conjugal Day. Twice a month, inmates get to have sex with their wives or girlfriends, while others begin new relationships with "letter writers" they've never met. The worst is when guys who are supposed to have sex, can't. Like the time when Frank was locked in the hot box in the yard. He asks Earl to find his girlfriend of seven years, Billie and explain that he's not blowing her off. Frank shows Earl a naked picture of Billie, featuring a wing tattoo in a very private place.
The eighth month of pregnancy is having an impact on Joy's everyday life. She's having a hard time playing pool with Darnell at the Crab Shack when she accidentally messes her pants. She runs for the ladies room, where Catalina sees her and snaps an unbecoming cell phone picture. Meanwhile Billie is pissed that Frank got himself locked in the hot box. When she finds out that Earl saw her naked picture, she tells him to tell Frank that it's over, ignoring Earl's advice that people deserve a second chance.
Joy doesn't like being blackmailed by Catalina. She can't blackmail her back, since everyone already knows everything bad about Catalina, so Joy decides to kill her with poison cookies. Darnell suggests trying to be nice instead. Earl starts a new list, and adds Billie to it, but Frank goes into deep depression and gives up, which makes him a target. Earl decides the only thing to do is to get Frank a new girlfriend, and the only choice is to find a letter writer, using a website called Convict Match.
Earl's lonely too, so he has Randy post a video for both him and Frank on Convict Match. Meanwhile, Joy gives Catalina a piÃ±ata, but the blackmail continues, so she decides to steal Catalina's phone. Cute Lucy shows up for a conjugal visit with Frank and they adjourn to the bedroom, while Earl struggles to make conversation with his date Annie, who's a pre-op transexual. When Frank grabs a radio antenna to pierce Lucy's belly button so she looks more like Billie, Earl promises to get Billie back.
Catalina's already downloaded the photo of Joy from her phone, so Joy's back to square one. She decides to bake some poison cookies with laxative instead of poison, then lies in wait for the big moment at the Peach Pit. Earl decides that Billie needs something to make her feel safe. Randy helps Earl put a naked photo of Frank on a billboard where Billie's sure to see it, asking her to come back.
Billie visits Frank on Conjugal Day. He runs off to steal flowers from another convict's memorial site, asking Earl to tell Billie he'll be right there, and nothing else. Billie explains that Earl's advice about second chances prompted her to enroll in nursing school, which she's going to quit now that she and Frank are getting back together. She had just graduated from community college on the day she met Frank, and somehow their relationship led her astray, as she tried to take on his hobbies of thievery and mayhem.
Earl and Billie agree, it feels good to do good. Earl finds himself in a rough spot, and has to make a choice between helping someone on his list and helping someone who really deserves it. As much as he knows Frank wants Billie back in his life, she needs to not have him in hers. Earl tells Frank that if he really loves Billie, he'll let her go.
After breaking up with Billie, Frank feels like a decent guy for the first time ever, even if it's not as nice a feeling as high-fiving himself in the mirror when he's doing a hot chick. Frank throws the naked photo of Billie in the garbage. But Earl can't stop thinking about Billie. It's good to know that there's someone out there working to do good things after years of doing bad, like him. He rips off the naked part of the picture and throws it away, keeping the picture of Billie's face.