Jack confides that he thinks Brad's playing some kind of game with him after he tried to hide from Katie the fact that Jack was on the phone by calling him "Emma". Margo urges Jack to get in touch with Katie and get the story firsthand and get all their feelings out on the table. Katie dreams of being with Jack, then is upset when she wakes up in bed beside Brad. Brad reminds her that they got drunk and talked, but nothing else. Brad cuts himself after showering and his towel falls, as Katie sees him in the raw. Katie tells Brad to go ahead to work, as she rushes off to see Jack. Jack is looking for Katie and learns from Brad that things have gotten a lot more personal between him and Katie. Brad tells Jack he was naked with Katie and she liked what she saw. Katie arrives and wonders what she liked? Gwen worries to Will that Adam and Jade won't rest until they've done all they can to destroy them. Will calms Gwen, who is appreciative, but wants to know how he really knows it's over. Jade thinks she's convinced Cleo to leave town and orders her to meet her at bus station in an hour. Cleo dresses up like Gwen, when Barbara appears. Barbara asks if she's heard anything from Adam recently, and "Gwen" is nonchalant. Barbara wonders what's wrong with her, as Cleo plays catch up with Barbara. The two bond, and vow to start anew. After Will lights in her, Jade runs into Gwen and assures her she's not doing anything to mess with Gwen's life. Jade, livid about no-show Cleo, runs into Barbara who tells her that "Gwen" has changed her outlook. Jade, having just run into the real Gwen, realizes Cleo must be at the cottage, as Cleo comes face to face with Will.
Katie demands that Brad explain what he told Jack about their night at the inn, but Brad evades. Katie tries to clear the air with Jack, but he says goodbye to Katie. Later, Emma thinks Jack over thought things. Jack says it's too late to tell Katie how he feels about her. Will knows Cleo is not Gwen and asks if Jade is behind the deception. Cleo pleads with Will not to call the cops, as Jade packs up and destroys the evidence of her plan. Will lets Cleo go, and when Gwen arrives, he tells her about Cleo. Jade orders Cleo to leave town, but it's evident that Cleo plans to stay in Oakdale. Casey wants to know why Maddie isn't happy about her college acceptance letter. Maddie admits that she won't go to Wesleyan because she wants to be in Oakdale when he gets out of prison. Casey pleads for Maddie to go to Wesleyan, and Maddie leaves, not wanting to spend the night.
At the Lakeview, Maddie turns to Vienna to talk about her sadness with Casey going off to jail for the next six months. She is confused at Casey's wanting her to go off to college and doesn't quite understand why he doesn't want her to stay nearby. Both women convey their sadness over not having Henry to talk to, but in his absence Maddie opens up to Vienna and tells her about her conflicted feelings over going away to college or staying around to support Casey. Vienna explains that Casey just wanted her to be happy by letting her go to college and live her dream. As Henry listens to the two talk, Vienna encourages Maddie to enroll in college and make herself a better woman for when Casey gets out of jail. Vienna tells Maddie not to "give up her dream for a man" and that Casey loves her for who she is, dreams and all. Henry approaches the two and hugs his sister as she runs out to see Casey. As Vienna stands to leave Henry asks for five minutes of her time and thanks her for being so wonderful with Maddie.
Tom and Margo try to comfort Casey on his last morning home before going to serve his sentence. Gwen and Will arrive to wish their friend luck and discover he is upset after his fight with Maddie the night before. As Casey explains about their fight he attempts to leave to find her and when Will tries to stop him he bolts past him to "say goodbye to the woman he loves". Will restrains Casey and reminds him of everything his parents have done to give him freedom. Casey agrees to stay and Gwen asks to talk to him alone. Gwen apologizes to Casey for the mistakes she and the others made that lead to his serving jail time. Casey tells her she has nothing to apologize for and that "his lies" have just caught up with him. Gwen and Will leave after promising Casey they will be here for him and will look after Maddie. Once they have gone, Margo and Tom tell Casey to be strong and that the six months won't be forever. Casey thanks them for being such great parents and turns over his great-grandfather's watch to Tom until he returns and earns the right to wear it again. Tom tells Casey that he and Margo set him up with a job at the prison and as they prepare to leave a tearful Maddie arrives to say good-bye. The two share a final few moments together and convey their love for each other as Tom and Margo tell the two it is time for Casey to go to jail.
Gwen and Will return to their home where Gwen tells Will about her conversation with Casey and his guilt over the bonds and abandoning her while she was pregnant with their child. The two discuss the idea that Casey believes his going to jail is for every mistake that he made over the past few years. This causes Gwen to worry that she will someday pay for her part in helping to bury Adam in the woods. Will tries to change Gwen's attitude and asks her to count her blessings and to live in the present. He encourages her to finish her demo and start singing live again. Will leaves to go to class and Gwen is left alone at the house, but not for long. Cleo arrives with flowers and introduces herself to Gwen as "her biggest fan".
During her morning shift at Al's Diner, Alison steps outside and snorts some of the drugs she purchased from the local drug dealer and is overheard by Emily as she comments on how she is running out. Emily questions Alison's outburst and she insists that Emily just caught her having an allergy attack. When Emily inquiries continue about Alison's new energy and great mood, Alison tells her there is nothing to worry about. Alison excuses herself and goes back into Al's followed by Emily. Inside Emily relays her sympathy to Lucinda over losing World Wide and reintroduces her to Alison. While the two are alone for a moment, Alison talks about her memories of good times with Lucy's and then in the middle of their conversation Lucinda makes a secret proposition to Alison. She immediately tells Lucinda that it is interesting that she would be asking her to do something because Paul Ryan has already been after her with a secret offer. Lucinda lets her know that she and Paul are working together and that Alison is lucky to get the offer. When Alison questions Lucinda about what they need her to do, Lucinda gives her a hundred dollar bill with a note that has an address and time and tells her to prove her worth by meeting her on time. After Lucinda leaves Emily returns and asks Alison if she is ready to go for their day of beauty. Alison quickly puts Emily off by telling her she needs to attend a meeting for her drug abuse and she leaves Al's to meet with Paul and Lucinda.
Earlier at the farmhouse, Paul arrives and greets Meg with a hug that lifts her off her feet. Meg reminds Paul that they shouldn't be seen together, but both agree they miss one another. When Paul asks Meg what her plans with Craig include, she tries to persuade Paul that she is just gaining Craig's trust and that even though he kissed her she wouldn't let it go any further. Meg insists that she isn't trying to hurt Paul, but Paul tells her that his only concern is Craig hurting her. With that thought he tells Meg that she is out of the plan to get back at Craig. Meg lashes out and lets Paul know she has done too much "ground work" to let go of her part in the plot to bring Craig down. After much prodding, Paul tells Meg that Alison Stewart is the key to his plan because of her voice sounding just like Rosanna. He explains that he and Lucinda will use Alison to trick Craig into thinking that Rosanna is out of her coma and has returned to tell the police that he is the one who ran off the road. Paul is convinced that Craig will be so tormented by Alison's impersonation of Rosanna that he will confess everything and go to jail. Meg reminds Paul that Craig will need someone to confide in and as long as she stays on his good side she can be that person. Meg persuades Paul to let her help and as the celebrate their agreement with a kiss Lucinda calls and tells Paul everything is going great with Alison and to meet her as planned. Paul takes leave of Meg but asks her first to make sure she tells him the next time Craig comes around.
Paul and Lucinda meet at a hotel to discuss their plan for destroying Craig. While there Alison arrives and questions the two about what kind of job Lucinda and Paul want her to do. Lucinda tells Alison she isn't doing anything illegal and she will be paid very well for just a little work making a few phone calls. Alison's curiosity is aroused and even though at first she is wary of the plot, she soon warms to the idea of working with Lucinda and Paul.
Alison hears the recording and comes to the conclusion that Paul and Lucinda are asking her to impersonate Rosanna. Paul and Lucinda realize they have to tell Alison about Craig. Alison's nervous and can't perform, but after a quick run to the bathroom, she's ready to go. Later, Alison goes off happily with her cash and buys meth. Meg cautiously leads Craig to believe they have a future, and he invites her out for a drink – then is thrown when he gets a call from "Rosanna." Spooked Craig cancels his drink date with Meg, and tries to trace the call. Rosanna's doctor informs Craig that she's disappeared. Will breaks the news to Barbara that she was really having a heart to heart with Cleo, not Gwen. Barbara wants to go after Jade but Will thinks that's a bad idea. Barbara insists on going to talk to Gwen, but Will urges Barbara not to belabor this, and assures her that Cleo has probably already left town. Cleo's arrived at the cottage, but Gwen's not receptive and calls the police – then Cleo faints. When Cleo seems too shaky to leave, Gwen offers to get her some juice. Gwen gently invites Cleo to admit she's involved with Jade. Cleo's denial about being involved with Jade turns into her urging Gwen to keep on with her singing career. Cleo, relieved at Gwen's thaw, hugs Gwen just as Will comes home. Cleo leaves but secretly sticks around to observe Will and Gwen.
At the Snyder farm, Jack finds a copy of a children's book called "Stevie and the Mysterious Alphabet House" in the trash; taking it inside, where Parker and Faith are talking, he shows it to Parker and reminds him that his mom gave it to him when he was little. Parker says it's a kid's book and he doesn't need it anymore; Jack suggests he keep it up in Emma's attic in case he changes his mind. Jack has to leave to go to the station, and when he does, Parker tosses the book in the trash again. Faith asks him what the book is about, and he tells her it's a story about a boy who gets lost in the woods and has to use the things he finds to help him get home. When he goes upstairs for a minute, Faith fishes the book out of the trash and puts it in Parker's backpack. Parker comes back downstairs and finds the book; turning, he looks at Faith, whose back is to him, then turns back around, smiling slightly, and puts the book back in his backpack. Faith turns around and smiles.
At WOAK, Kim receives a phone call from an anonymous woman who says she's in the town where Brad and Katie are going to meet the WOAK contest winner, and if she lays eyes on Brad, he's a dead man. She hangs up, and Kim is concerned enough to call Jack and explain the situation to him; she asks if he would go to the town if she clears it with Margo and gets her housekeeper to babysit Jack's kids for him. He agrees to go because Kim is so concerned that something might happen to Brad or Katie.
Brad and Katie fly to the home town of the contest winner to meet her. Brad acknowledges having been to the town before but doesn't say much about anything that happened there. When they arrive at their hotel, the local TV producer shows them to their room and gets Katie to autograph a copy of "Oakdale Confidential" for his niece. He tells Brad and Katie that they are exactly the way they seem on TV. Katie has to leave to go to hair and makeup, and Jack arrives while she's gone; he tells Brad about the threat, but Brad says he has no idea who might have made the phone call. He tells Jack he's not the same guy he was when he was last in town, that he's a changed man now that he's got "a good thing going" with Katie. Katie walks in, and Brad has to leave for his turn at hair and makeup. Jack tells her it seems like she and Brad are clicking now, and she agrees. Before Jack can leave, Katie says she thinks they need to talk; when he asks what about, she replies, "You and me."
At the Lakeview, Ali and Emily are having breakfast, although Ali's only drinking coffee. Emily thinks she seems jittery and isn't eating enough, and she tries to get Ali to tell her about the support group meeting she supposedly went to yesterday; Ali offers vague details about the meeting, then she gets a call from Paul. She pretends she's talking to Will, and she asks Emily if she can go meet Will and Gwen for coffee; she says her counselors say she needs to spend time with the friends she had before her drug problems began. Emily agrees that she should go, but as Ali is putting on her sunglasses and leaving, Dusty walks up and wonders where she's going. Alison leaves, and Dusty says the sunglasses and the lack of eating ought to be making Emily suspicious. Emily says Alison can't afford drugs based on what she's making at Al's Diner.
Craig tells a private investigator that Rosanna has disappeared, and he needs to find her. Meanwhile, at Montgomery Enterprises, Lucinda and the board members are waiting for Craig so a board meeting can begin; she hints that perhaps this takeover is proving too much for Craig to handle.
Alison goes to meet Paul; she takes one of the chocolate bars from the refrigerator in the hotel room and eats it. Paul becomes concerned about Alison's behavior and all the sugar she's eating, when Lucinda sends him a text message saying, "We're on."
At the board meeting, Craig enters and apologizes for keeping them all waiting. His assistant comes in and says there's a woman on the phone who says she urgently needs to speak to Craig but who won't give her name; Craig excuses himself and takes the call. It's Alison, impersonating Rosanna as she says, "I know you tried to kill me, Craig." Then Paul drops a vase and shatters it so that Craig hears the sound of breaking glass. Alison hangs up, and Craig, shaken, returns to the boardroom; he apologizes and says he'll need to reschedule their meeting. Lucinda says the next time might not be convenient for her, and he suggests that her presence is not necessary. She says someone needs to keep an eye on him, and he explodes, saying, "This is MY company!" Lucinda tells him not to lose his cool, and then she tells the board members, "In my day, we got things done." Craig goes to Fairwinds, and when he goes to pour himself a drink, he sees a shattered photograph of Rosanna on the floor. He calls the housekeeper in and demands to know how that happened, but she has no idea; she says it was fine when she dusted this morning, but then she had to go to the market. Craig says someone's been in the house, and after the housekeeper leaves the room, he says, "She did this!"
At the Lakeview, Dusty shows Emily a mockup of the front page of the Intruder newspaper, and Emily says it's all wrong because of the Intruder's target audience; Dusty is impressed with her take on it and says he'll call the office to have them change it. After he leaves, Cheri walks up and joins Emily, saying she'd really like to have her back in the fold and will make their split 70/30 if she'll come back. Emily insists that part of her life is over now, saying she has people who are counting on her. Dusty returns, and Cheri leaves; Emily fills Dusty in on Cheri's offer, and when he asks why she turned Cheri down, Emily tells him the story of how she accidentally stumbled into prostitution in the first place, saying that although it felt empowering in the beginning, it turned out to be much different from what she wanted. She tells Dusty seeing Alison in that movie is what saved her, and now she needs to save Alison. Dusty leaves to go to the office, and Emily goes back to get her purse. Turning to leave, she almost bumps into Alison and Paul.