At the Lakeview Bar, Lucinda tells Dusty that Lucy is working undercover to find out the truth about Damian's medical condition. Dusty offers to help protect Lucy, but Lucinda tells him that he is more of a danger to Lucy that Damian is. Lucy discovers that Damian had been treated at Oakdale Memorial in the past, so she hopes to find a clue in his old records. Damian is visited at Fairwinds by Sergio Francone, who warns Damian that his time is running out.
Carly surprises Simon by joining him on his trip to New York City. When she arrives in her hotel room, she is delighted to find an entire new wardrobe. Her happiness turns to dismay when Simon barges into her room, telling her that his room is flooded. While Carly is in the shower, Simon answers her cell phone. Jack, on the other end, is shocked to hear Simon's voice.
At the police station, Margo tells Dallas that she thinks that Maddie's wounds were self-inflicted. Dallas does not agree, so he returns to look at the scene of Maddie's accident to see if he can find something that will clear Maddie. Maddie is beginning to worry that she might be the killer. She tells Henry that she is afraid that she is losing her mind, and Eve asks Margo to recommend a psychotherapist. Gwen sees Will having a conversation with Jade, and it is clear that the two share a secret. When Will arrives home, Gwen asks him point blank if he slept with Jade.
Mike and Katie learn Simon and Carly are together in New York. Mike tells Katie not to worry about it and focus on them, instead. Katie promises to do just that. But, when Kim tells her she needs to take a business trip for WOAK, Katie jumps on the opportunity to go to...New York. Where Simon is busy blowing off Jack, who's called on Carly's cell phone. Carly is furious and demands Simon leave. But he challenges her to think about what she really wants out of life and how bright their future can be together. Carly and Simon head out for a night on the town. Eve is upset about Maddie and, after Henry suggests they spirit Maddie out of town, she and Jack commiserate about always having to be the responsible ones in their families. Casey has snuck in to see Maddie, but she warns him to stay away and calls for Margo. Jessica comes to represent Maddie and counsels her not to say a word. Jessica convinces Dallas to let Maddie go and advises him to look at the case with new eyes. Dallas considers Jade as a suspect, then decides to return to Chicago and find out what really happened to Maddie. Will confesses to Gwen that he slept with Jade, but swears it meant nothing. He begs her forgiveness, but to her it's just Will telling another lie. Gwen leaves Will. He explodes with rage.
At the cottage, Mike gets Katie's message and leaves. On the plane, Katie thinks she sees Mike there telling her "this is wrong" but is mistaken. She tries to call home again but is stopped by the flight attendant. Katie heads home to an empty house and figures Mike went to the airport after her but he returns as she is about to leave. After talking, Katie asks Mike for a baby. At first unsure, he agrees and they head upstairs.
At Fairwinds, Luke comes down to talk to Damian. He wants to go back to the house to get a few things he needs to finish packing but Damian dissuades him, telling Luke they will send for anything he needs, if he is there long enough to need them. Sergio, who is watching Holden and Lucy talking, calls Damian. Holden leaves and heads over to Fairwinds and demands to see Luke right away. He tells Luke that he thinks Damian is faking everything to manipulate Luke and fills him in on his and Lucy's plans. Luke is upset with Holden for interfering and tells him he doesn't believe Damian is faking his illness. He tells Holden that Damian has changed and if Holden doesn't want Luke to leave, he'll have a hard time stopping him.
Dusty is at the hospital having Johnny examined and spies Sergio following Lucy. She enters the records room and searches everywhere for Damian's real medical file but comes up empty handed. She becomes frightened when someone tries to enter and almost hits Dusty with a lamp. He tells her about the man following her and tells her to stop her search before she gets hurt. Lucy tells him to butt out. They leave and run into Holden in the hall and both men express their concern for her safety but Lucy won't back down. Sergio calls Damian back and fills him in on Lucy's search and says it is a good thing he already removed Damian's file before she got there.
Will comes up on Casey at the pond. Will tells him about sleeping with Jade on graduation night. Will asks Casey to speak to Gwen for him but he tells Will that he should fight for Gwen. Back at Crash, Gwen comes in looking for Casey but Jade arrives instead. Gwen calls her on sleeping with Will. Jade tries to make it look as though Maddie is spreading rumors but changes her tune after Gwen slaps her. The two have it out and Jade defends Will and herself and tells Gwen she should get over it. Gwen is disgusted over the actions of her so-called friend and her manipulative ways, including getting money and a place to stay out of her and Will. Casey arrives and sends Jade away so he and Gwen can talk. He lends her a shoulder to cry on and tries to convince her not to make any major decisions yet regarding her marriage. He tries to get her to go home but she prefers to stay at Crash. If she stays, he stays Casey tells her. Back at the house, Will arrives and considers calling Gwen but doesn't. Jade shows up and tries to get Will to remain friends with her and let her talk to Gwen for him. Will wants nothing more to do with her. He sends her away and hopes for Gwen to return.
At Crash, Gwen awakes alone for the first time in her torn marriage. She meets Casey and he pushes her to go talk to Will. He says she shouldn't give up on him, just like he hasn't given up on Maddie. Gwen is surprised when Casey tells her of how Maddie turned him away when he tried talking with her at the police station. She convinces Casey to go see Maddie. Gwen then goes out to look for Will. When she finds him at Java with Jade, she quickly goes away in tears before being seen, bumping into Barbara. Gwen tells Barbara her marriage to Will is over since he slept with Jade. Totally taken aback by this, Barbara goes inside to confront her son. She tells him she just ran into Gwen, and Will tries to go out to see if she's still there, only to find she has already left. Barbara has a talk with her son, telling him he shouldn't go after his wife. Instead, she offers to try to talk with her. At first Will flat out refuses, but then he agrees with his mother's plans.
Eve meets Henry and Maddie at the Lakeview with a surprise: her husband Louis. Henry and Maddie aren't exactly thrilled that he is here and Maddie shows her displeasure by dodging Louis's greeting hug. Maddie is disgusted by the fact that more of her relatives are coming to Oakdale to try to get through to her and she storms off. Just as she leaves, Casey arrives. Louis immediately suspects Casey has something to do with Maddie's situation and questions their relationship. Casey counters by questioning Louis's relationship with his sister-in-law and the two begin a heated exchange. Eventually, Casey leaves and Louis believes he is trouble. He chastises Henry for not paying more attention to Maddie. Louis finally claims that he can get Maddie to open up.
At Fairwinds, Luke now knows Lucy is trying to uncover the truth about Damian's illness. He confronts Lucy and she tells him she still thinks Damian is faking his illness, but Luke is adamant on going to Malta with Damian. Luke tells her cousin the two are leaving in a few hours, and the two share a goodbye. When Luke leaves, Lucy makes a quick phone call and asks a co-worker to fill in for her claiming "her grandmother is very sick and she has to care for her." Unbeknownst to her, Sergio is spying on her again. Sergio tells Damian that Lucy is up to no good and warns him he and Luke must leave as soon as possible. Meanwhile, Dusty admonishes Lucinda that her granddaughter may be in danger. He tells Lucinda that a man possibly working for Damian was spying on her at the hospital. Lucinda takes Dusty's word for it, but reassures him that Lucy is out of harm's way at the hospital. Dusty goes to the hospital to check on Lucy, but finds out she isn't at the hospital after all. He wonders what Lucy is up to.
When Lucy finds out Damian and Luke are leaving soon, she makes his last few hours in Oakdale worth his while and passionately kisses him. Before things really heat up, Lucy tries to pry into Damian's personal life and asks him questions. While she serves him and herself some tea, she slips an anesthetic into Damian's tea. Damian drinks the tainted tea and after a while begins to feel tired and it appears he is out cold. Seizing her opportunity, Lucy gets out her needle, hoping to draw blood from Damian. But before she can insert the needle into his arm, Damian grabs her hand.
Luke meets up with Jade at Java and finds out she slept with Will and ruined his marriage with Gwen. Luke is surprised that Jade is unashamed and she tells Luke that Will is better off without Gwen. Meanwhile, Barbara tries to talk with Gwen and pleads with her to give her marriage a second try. She claims that Jade seduced and used Will, but Gwen insists Will is partly to blame as well. The two are interrupted when Casey walks in. Barbara leaves Casey and Gwen alone and Gwen reveals to Casey that she found Will and Jade together. She insists on not moving back to her home with her husband, and Casey offers Gwen to stay at his place for a while. Gwen happily agrees and the two hug while Maddie jealously looks on. Later on, Gwen packs up her things and senses someone else is in the room. Seeing no one is there, she continues packing. Suddenly, Maddie intentionally smashes a vase on the floor, startling Gwen.
At the Lakeview, Henry, Eve, and her husband, Louis, are discussing Maddie's problems. Louis insists that Maddie trusts him and will listen to him, saying he's been like a father to her and that Henry has been too absent or too soft on her. Louis says no matter what they might think, the truth is that Maddie has "never been normal." Henry tells Louis that it's not every day that a "fatuous know-it-all" tells him his sister is "a nut job," and Eve asks both of them to stop so they can work together to help Maddie before she hurts herself, or someone else.
Barbara shows up at Will and Gwen's place and tells him about her conversation with Gwen. Barbara tells Will that they need to do some damage control and that she's already started, by planting the idea in Gwen's mind that Jade manipulated both of them from the beginning. Will becomes angry, telling Barbara this was all his fault and he doesn't want to pin all the blame on Jade and play games with Gwen like that. He asks Barbara to leave, which she does.
At Crash, Maddie approaches Gwen angrily and asks what she's doing with Casey. She tells Gwen she overheard her talking to Casey about moving in with him and says that just because she and Casey broke up doesn't mean Gwen "gets" Casey. She then tells Gwen she'd better stay away from Casey or she might end up dead like Lia. Gwen leaves, and Jade walks in and tells Maddie that people are out to get her because she ruined Will and Gwen's marriage; Maddie says if anyone needs to be "punished," it's Jade. She tells Jade that it's Jade's fault that Gwen and Casey are now a couple, telling her she saw them hugging and heard them talking about Gwen going home with Casey; Jade tries to tell her there's another explanation for all of that, but Maddie doesn't listen, telling Jade it's wrong and it's not going to happen. Jade tells Maddie not to make trouble, and hearing that, Maddie flashes back to a man's voice telling her the same thing; she runs out of Crash without any explanation.
At Java, Luke asks Jade what she means when she says, "Gwen won't be around much longer," telling her that's an odd thing to say with a murderer on the loose. Jade tells Luke that's not what she meant and wants to know why one minute, he's asking her for a favor and the next, he's on her case. Luke thanks her for agreeing to keep him posted about Lily's condition, but he suggests she learn to butt out of other people's business while he's gone. Holden arrives to meet Luke, and Jade leaves. Luke tells Holden that he and Damian are flying to Malta tonight. Holden is upset to hear this but says that it's like when Luke told Lily and him about being gay: he was taking control of his own life, and Holden respects that. Luke manages a choked-up goodbye, and after embracing his father, he leaves. Holden gets on the phone and asks Jack to meet him right away. When Jack arrives, Holden asks him to somehow help stop Damian from leaving the country tonight, so that Holden can find out why Damian really wants Luke to go to Malta. Jack agrees to do what he can to help, provided it doesn't get him in any more trouble at the police department.
At Fairwinds, Damian tells Lucy he knows she tried to drug him and that he'll have to ensure she can't tell anyone else about her "diagnosis" that his medical condition is being faked. As Lucy begins to feel faint, she realizes that Damian switched the tea cups, and he has now drugged her. As she collapses, he picks her up and carries her down to the wine cellar. Upstairs, Dusty comes in and finds a syringe and a tea cup lying on the floor, and when Damian walks back into the room, he demands to know where Lucy is. After Damian tells him to go away, Dusty pretends to leave, but he returns and sneaks down to the wine cellar, where he finds Lucy. Before he can rescue her, Sergio appears with a gun, and he ties up both Dusty and Lucy and then leaves. Lucy yells for Luke, but assuming he won't hear her, she turns to Dusty and says, "It's like old times, isn't it?" Meanwhile, upstairs, Luke has returned; he asks Damian where Lucy is, because she promised to stay to say goodbye to him, and Damian makes it sound like she was called back to the hospital. When Luke calls the hospital, he's told that Lucy's not on duty today, and he gets angry when Damian tries to tell him they don't have time to track Lucy down; Damian reacts to Luke's anger by looking like he's feeling ill, which makes Luke feel guilty. He tells Damian it's not that important for him to find Lucy, and they get ready to leave for Malta.
Gwen goes home to pack her things; Will hopes she's there to talk things over, but as he tries to explain to her how things happened between him and Jade, Gwen becomes upset and tells him she can't talk about that right now, that she's moving out. Will says he doesn't want to lose her; she says she doesn't want to lose him, either, but she thinks it's already happened. When Will asks where she'll go, Casey walks in and tells Will that Gwen is going home with him. Will becomes angry, saying Gwen apparently has been able to forgive Casey but can't seem to do the same for him. Thinking this means that Gwen and Casey are becoming a new couple, he tells them to stay at the house, and he'll leave; Casey responds by saying, "While you're gone, if you could ... I don't know ... grow up? That'd be good." Will storms out, and Gwen starts crying, telling Casey she's a loser. Casey objects to that and tells her Will's big problem is that he never thinks anything is his fault; Gwen asks him not to disparage Will, even if he thinks it will make her feel better, because it doesn't help. He promises not to do it again and suggests they leave. Gwen realizes she's packed all the wrong things, so Casey offers to go in the bedroom and grab more things out of the closet for her. Someone outside opens the window and climbs in, wearing dark clothing and carrying a knife. The person approaches Casey from behind and hits him on the head, knocking him out, then goes into the living room and hits Gwen when she turns around, knocking her down; the attacker then straddles Gwen, holding the butcher knife over her chest.