Alison tries to score some meth, but Paul inadvertently interrupts. When she suggests he leave her and her sister alone, Paul reels at something that seems familiar. Fearing he recognizes her from porn, she splits fast. Gwen and Will see Alison and invite her to join them. But in the midst of trying to score some drugs, she emphatically says no. Alison backpedals, apologizing for refusing their invitation so abruptly. They go off to buy books as Alison approaches Jesse once again. Shaken Paul pulls out a hidden photo of Rosanna while he remembers Alison's voice. Margo tries to cheer up Casey with his impending sentencing. Tom and Margo take Casey to sentencing and Gwen, Will, Maddie show up for support. Casey asks them to take resistant Maddie to Al's and feed her. Later, ecstatic Maddie thinks he's back and got only community service, but Casey says that's not what happened. Maddie can't believe Casey has to go away so soon for so long, and Margo is devastated as it sinks in that Casey will be going to jail. Jade preps frustrated Cleo when Luke interrupts. Jade makes excuses to Luke and finally gets rid of him saying she'll meet him in Old town. She leaves, telling Cleo to stay put. Luke apologizes to Jade for blasting her over Lily's pill addiction. Jade's accepting at first but when Cleo shows up, Jade turns cold. Elwood shows up in Old Town and Cleo prepares to do a test-run. Elwood thinks it's Gwen, but later Jade threatens that she'd better not pull a stunt like that again. Cleo says she's tired of Jade's threats. Later, Elwood runs into Gwen, who disputes what Cleo's "Gwen" told him, as Jade and Cleo are worried as they see their exchange.
Jade sends Cleo back to the motel and interrupts Elwood and Gwen so he can't reveal his run in with faux Gwen. Jade calls Cleo and tells her the plan is to break up Will and Gwen for good. Cleo still worries about Jade's intentions, but Jade assures Cleo that she won't hurt Gwen. Cleo realizes that as faux Gwen, she'll make love with Will. Paul remembers hearing Alison's voice and how much it reminded him of Rosanna, as Meg reassures Lucinda that Paul is on her side. Lucinda suggests that if Meg wants to help her get back WorldWide, she poison Craig. Meg refuses to poison anyone and Lucinda leaves. Meg goes to Paul and tells him about Lucinda's request and Paul gets an idea. Paul can't fill Meg in yet – he needs to see if the person he's thinking of is willing to help them. As Alison haggles with the dealers, Emily and Dusty arrive and grow suspicious. Dusty and Emily want Alison to get a job at Al's, and realizing she needs money for drugs, Alison finally agrees. Later, when Emily lays down the law, Alison threatens to walk out. But Emily threatens to tell Susan the truth about Vegas. Paul calls Alison, wondering if she still needs a job. Alison agrees to keep his call a secret.
After Brad and Katie finish taping their show for the day, Brad tells Katie to expect that Jack will ignore her for a couple days to recover from their kiss. Offended and annoyed Katie sends Brad off to flirt with the stage manager as she flips through contestant's letters from the station's contest. Just then she receives a visit from Henry, still dressed in his tux and looking dejected after believing he has already lost Vienna to Brad. Henry, who thinks Vienna and Brad slept together, tells his inaccurate story to Katie and asks for her help in getting Vienna to forgive him. Katie asks him how he felt when he heard Brad and Vienna together and when Henry admits it upset him, Katie tries to convince him he must still love Vienna and that he needs to go to her. A pitiful Henry claims he couldn't bear the thought of hearing Vienna tell him he has been replaced by Brad and leaves the studio. Katie quickly turns her attention to Brad and lets him know with a punch to the stomach that she thinks he is a "disgusting pig". Before Katie can leave the studio, Brad confronts her and asks why she is so angry with her. When Katie tells him she knows he slept with Vienna, Brad denies the implication and tells Katie what really happened. At first, Katie refuses to believe Brad, but he convinces her with an accurate account of what took place. The good news that Vienna didn't sleep with Brad encourages Katie to believe that Vienna must still love Henry. Brad quickly rips into Katie and says she is being a hypocrite because all along she only wanted Henry to love her and didn't want him to marry Vienna in the first place. Katie denies Brad's accusations and to prove him wrong she tells him she is going to get Vienna and Henry back together by sending them both to the same romantic place. She convinces Brad to help her and he agrees to help, if only to see the entire plan blow up in her face.
At the Lakeview, Vienna opens the door to Emma who has arrived to return her wedding dress. When Emma tells her to hold onto it, Vienna claims she has lost Henry and he will never return. Emma invites Vienna to return to the farm, but she declines because it is filled with too many memories. Their conversation continues with Emma convincing Vienna that Henry will return to her, but in the meantime she needs to get out of her depressing hotel room and live her life. Emma's pep talk inspires Vienna to imagine that Henry has returned. Her fantasy is interrupted by a knock at the door and a visit from Henry. He apologizes to Vienna and tells her he wishes he was a good man. At first Vienna assumes Henry is apologizing for leaving her and wants to come back to her so she accepts his apology. But when Henry tries to give Vienna her money back she realizes that he isn't coming back to her and with that Vienna tells him she doesn't accept his apology. She lashes out at Henry telling him she wanted him to be different from all the other men in her life. She tells him to take the money and get out and pushes him out of the room.
After his run-in with Vienna, Henry quickly heads to the bar to drink away his problems. Katie hurriedly finds Henry and tells him an elaborate story about having to go to an inn to do a story for Oakdale Now. She begs Henry to go with her and he finally relents. At the same time Brad goes to Vienna's room and quickly persuades her to go with him to same inn. It looks like Katie's plan to get the two back together is unfolding well.
At Casey's house, Maddie, Will and Gwen arrive with balloons and a cake for Casey, but their surprise angers Casey and sends him storming to the front porch. A frustrated Casey tells Maddie that he doesn't want them to see him go to jail. As the two finish up their conversation and begin to kiss; Maddie talks about how she wants to make love to Casey. He puts a stop to Maddie's declaration and tells her she can't talk like that because there is a good chance his parents could be home anytime with the cops to take him off to jail. With that the two head inside and Casey open gifts from Will and Gwen which includes comic books, CDs, and stationary. All of the gifts are for his time in prison. Tom and Margo arrive at home and let Casey know the judge has given him two days of freedom before he has to report to jail. They tell Casey they put up $100,000 bond, by mortgaging their house, and the judge agreed to let him off house arrest before he heads off to serve his sentence. Gwen and Will go to leave the Hughes' house to set up a romantic rendezvous for Maddie and Casey at their house. Before Maddie and Casey can head out on the town, Tom tries to find out what their plans are. Casey promises Tom that he and Maddie will be safe and with that the two leave for Will and Gwen's house.
Earlier at Will and Gwen's house, Cleo searches the front porch for the key and breaks into their home. Upon entering she looks around and declares the place, "Feels like home". Cleo takes out a note pad and begins to look around the house to try to get a feel for Gwen's life with Will. She goes into the bedroom and lies on the bed and props up pillows pretending they are Will. As Cleo remakes the bed and begins to leave she finds Gwen's dresser and begins to search through it. Gwen and Will return home and just as they go in the two stop and discuss how Will felt when he went to the hospital for killing Rose. He understands how Casey feels and is glad he can be there to help him through his jail sentence. Inside Cleo tries on Gwen's clothes and is forced to hide when Will and Gwen set up for Casey and Maddie's arrival. As Maddie and Casey arrive, Cleo sneaks out the bedroom window undetected and Gwen and Will leave the two alone. Once alone at the house the two make love. Afterwards Maddie begins to cry and tells Casey now it is harder then ever to watch him go. Casey holds her and tells her he loves her and they will be together in six months when he returns.
Back at the Wagon Wheel, Cleo practice being Gwen and tries on her clothes again. After numerous trials and errors at getting Gwen's voice down, Cleo declares she is Gwen Munson. Meanwhile, Gwen and Will study at Al's Diner and as Gwen checks her email she finds a message from Carly.
Will questions Gwen about Carly's e-mail, but she hesitates, as the message specifically asks her to tell no one and meet her in Montana. Later, Maddie examines the e-mail, and surmises that Jade sent it, not Carly. Angry Will calls Jade and warns that he and Gwen are onto her. Later, Will points out to Gwen that if the e-mail really was from Carly, she'll reach out to Gwen again. Jade interrupts Cleo fantasizing about being Gwen. Jade alerts Cleo that Will and Gwen have discovered their plan and Gwen won't be leaving town. Cleo insists Jade give her a chance at running things. Jade discovers Gwen's stolen clothes and calls off the plan, but Cleo insists it's not over yet. Parker and Faith skip a school pep rally, and Parker admits that he wanted to spend time with her. The two open up about their family issues. Parker tells Faith she's cute and they share a bonding moment. Henry discovers that Katie has set him up for a romantic run-in with Vienna. Henry tells Vienna about hearing her with Brad the day after their ruined wedding. Vienna explains that Brad turned her down, and insists that a weekend together won't make Henry love her. Later, Henry sees Vienna taking care of Maddie and he's struck by her softer side. Jack walks in on Katie carrying sexy lingerie. Katie says to Jack that they should forget about their kiss, and confides in him about her plan to lure Henry and Vienna back together. Later, Margo reveals to Jack that Katie wants to explore what they have together. Brad calls Jack to announce that he and Katie are spending the night together, alone in the country.
In Old Town, Holden is talking to Natalie, who is reluctant to go on a sleepover at a friend's house because she doesn't know what to say about her mom going away. Holden reassures her that she doesn't have to talk about it at all, and he tells her Lily went to the hospital so she could get better and come back to be with them again. He asks Natalie to take a letter to the mailbox for him, and while she's gone, Lucinda, who has been eavesdropping, sits down next to Holden and tells him what a great dad he is. She hates it that he's the one suffering when it should be Craig who's in pain. She tells Holden to take care of himself, and he tells her to go after Craig, to bring him down and take her company back. Holden leaves with Natalie.
At the Lakeview, Meg is seated at the bar having a drink when Craig walks up to her. He thinks she's been sitting there waiting for him to walk by, but she says she's waiting for someone else. Craig assumes it's Paul, but Meg reminds him that she's "moving on." She eventually gets up to leave, saying the doctor must have decided not to waste his time with her after all. Craig says he hates hearing her talk like that and doesn't like to see her feeling bad about herself. He says he realizes now that maybe she does need to move on, and she says she's ready to move on, with the emphasis on him. She walks out, and he tries to follow, but she ducks around a corner and eludes him. Then, Meg calls Paul and leaves a message saying she thinks she's hooked Craig, but they'll have to be careful reeling him in.
Emily runs into Dusty at Old Town and tells him happily that she and Alison had a great talk the night before, and she thinks she really got through to Ali. Dusty tries to make her realize that Ali's not out of the woods yet and that she can't let her guard down. Later, Dusty runs into Holden, who's dropped Natalie off and has been trying to take advantage of some time without any of the kids around. They talk about kids, and then they talk about Craig and how he's tried to ruin their lives; as Holden leaves, Dusty tells him Montgomery's going down sometime.
Alison gets off of work at Al's and sits down to talk to Paul. When he tells her he wants to make a deal with her, but she has to be discreet, she sounds as though she assumes he wants to pay her to have sex with him; when he realizes this is what she's thinking, he's part amused, part horrified, and part confused by her lack of concern about that kind of offer. She tells him she wouldn't have gone through with it anyway, but she says she's grown up a lot since she left Oakdale. When she asks again what the proposition is, Paul says Emily can't find out about it or the deal's off. Alison agrees, but Paul still won't tell her exactly what it's about except to say she'd have to play a role; he gives her $100 to keep her interested until he can explain the whole situation to her, then he leaves. Alison calls her drug-dealing acquaintance, Jesse, and tells him she'll meet him in 5 minutes, but Emily walks in and overhears her and tells her she's not going anywhere. They sit down to talk, and Alison alternately jumps on Emily for making her feel like a prisoner and apologizes because she knows Emily cares about her. Emily tells her she bought her a new dress, and maybe they should find something fun to do together tonight so Alison can wear it. She has Alison go change into the dress, and Ali takes that opportunity to call Jesse and ask him to hang around for a while until she can meet up with him. Alison and Emily end up having dinner at the Lakeview together, where a business man walks in and stops at their table, saying how lucky he is to have found the 2 of them together; he obviously recognizes Ali from her porn movies and Emily because he was a client of hers, but Alison doesn't know what the man is talking about. Dusty walks up and forcibly removes the man from the dining room; he tells the man not to go near them again, then he goes back to the table and tells Alison a lie about the man being a stalker who used to work at the paper. Alison can see that Emily wants to talk to Dusty about what just happened, and she tells her she can drive herself home, and Dusty can bring Emily later. Emily hands her the car keys, and Alison leaves, as Dusty sits and says, "I hope that wasn't a mistake." Emily thanks Dusty for covering for her, saying she deserves whatever she gets as a result of what she's done, but she doesn't want Ali to be hurt just because Emily's a fake. Dusty says she's not a fake and reminds her of the good things she's doing in looking out for her sister. Emily says she wishes she could see herself the way Dusty does, and he says, "Me, too." Meanwhile, Alison goes to Old Town and buys some meth from the dealer.
Paul gets into Lucinda's car, and she gives him some wine as she listens to his proposal to bring Craig down. They trade insults, until Paul becomes fed up and says he's leaving, but Lucinda stops him and asks him what he has in mind. Paul says he's taking a page from Craig's book and is planning to use the people Craig loves to manipulate him. Lucinda says, "Not Lucy, not Johnny, not Meg." Paul agrees that that's not who he meant, and Lucinda realizes he's talking about Rosanna. He tells her he ran into Alison Stewart and was stunned to find out how much she sounds like Rosanna. He tells Lucinda that he thinks he can pay Alison to impersonate Rosanna on the phone and make Craig think Rosanna has come out of her coma. After making sure Lucinda understands that he's running this show, Paul leaves, and Lucinda places a call to the medical facility in Switzerland where Rosanna is being cared for; she speaks to the director of the facility and reaches some type of arrangement with him. She hangs up, then asks her driver to take her to Al's for some food; she hopes to run into Alison Stewart there.
Meg goes to Emma's and finds Craig there, waiting for her. He says she seems to be in a good mood for someone who's been stood up, and he tells her he thinks that's because she enjoys the verbal sparring they've been doing. He tells her that he's decided not to be smart but to believe her when she says she's moving on, with him, and he kisses her. As she backs away from his attempt at a second kiss, Holden walks in and orders Craig to leave. He doesn't notice when Paul comes to the porch and listens as he tells Meg he just doesn't understand her at all, how she could let Craig touch her after what he's done to their family. Meg tries to explain, but Holden says he doesn't want to talk to her anymore, and he goes upstairs. Paul comes in and asks Meg what was going on; she says she didn't know Craig would be there, and Paul tells her that's the problem --- they don't know what Craig will do. Paul tells Meg that her part in trying to bring Craig down is over, and he'll do this his way, without her help.