As Katie and Mike start their honeymoon cruise, they are unaware that Katie's ex-husband is directly across the hall from them. Simon and his companion, Vienna, entertain rich potential "marks" with a loud party. When Katie pounds on the door and demands that they turn down the volume, Simon thinks that he recognizes her voice.
Luke angrily pushes Lily away, causing her to tumble down the stairs. Lily lies unconscious, surrounded by Holden, Luke, and Damian, until the ambulance arrives. Luke and Holden ride in the ambulance, while Damian takes time to send Ross Krieger on his way before he follows the ambulance to the hospital. Damian takes advantage of Luke's distress by offering to let Luke stay with him. Overcome by guilt, and afraid that Holden blames him, Luke agrees. Just before they leave, Lucy tells Damian that there is swelling in Lily's brain.
Paul accuses Emily of putting their unborn child at risk for a chance to win her freedom. Emily admits that she still hopes to share in the child's life. Jennifer enters Emily's hospital room and jumps to Emily's defense, making Paul and Meg leave the room. When Johnny's stem cell procedure is completed, Jennifer goes to Emily and thanks her tearfully, telling her, "Saying thank you will never, ever, be enough."
Damian tries to keep Luke from Lily, afraid that she'll wake up and tell him the deprogrammer was Damian's idea. Luke ditches Damian to head to the hospital. He tells Holden what happened with Ross, convinced his dad blames him. Lily regains consciousness and calls for her son. Carly summons Jack to come get his things. She informs him she's taking the kids and going to Montana for a while. Jack is surprised by her finality. She hands him the freshly signed separation papers. Gwen stops by and is shocked to hear Carly and Jack are over. Will asks Casey to give Jade a job at Crash. Casey refuses, afraid Maddie would kill him. Will begs Casey to ask Lisa. Jade throws her arms around Will in gratitude, which Casey sees. Will warns Jade to stay away from Gwen. Jade gets the job, just as Gwen walks in to see her with Will and Casey. On board the ship, Vienna steals Katie's room-service breakfast. Katie screams "Thief!" at her, alerting Simon. He's shocked to see his ex-wife but doesn't let her see him yet. Mike surprises Katie with a massage. Simon bribes the masseuse to let Simon take his place.
Simon puts on a phony voice and questions Katie about her love life while pretending to be a masseuse. When she starts talking about Simon, he drops the accent and reveals himself to her. Katie orders him to leave, but he kisses her instead. Mike arrives at the door. Gwen wants to know how Casey could have hired Jade. Will says it was his idea. He felt guilty about Jade losing her library job. Gwen wants to know why he kept it a secret from her. Will convinces Gwen that Jade deserves a second chance – just like they once did. Gwen sees his point. She unveils a surprise for Will – they're house-sitting for Carly! Privacy at last! Meanwhile, Maddie is equally furious about Jade's hiring. As she and Jade fight, Jade lets it slip that she was with Will graduation night. Holden demands to know Damian's role in the scheme to reprogram Luke. Damian denies knowing anything about it. At the same time, Lily struggles to wake up and speak to Luke. Holden wants to know what Luke did to upset his mother so much. Damian defends his son, deliberately driving a wedge between Holden and Luke. Lily slips into a coma. Luke wonders what she so desperately wanted to tell him.
Jade claims to Maddie that, graduation night, all she did was tell Will to go find his wife. Meanwhile, Will and Gwen are enjoying being alone at Carly's when a call from Barbara about Johnny sends them running to the hospital. Elsewhere, Maddie and Casey decide it's time for them to have sex and head to his house, since Casey's parents are away for the weekend. Paul wants him and Dusty to work together to stop Emily, but Dusty wants no part of Paul. Jennifer thanks Lucy for her help with Johnny. Lucy notices Jen isn't looking well herself. Lucy bends some rules to get Jennifer a meeting with Emily. Emily asks for a favor – she wants her and Jennifer's children to be close; after all, they're cousins. Dusty arrives to declare: Over my dead body! Will notes that Dusty is starting to sound a lot like Paul. Jennifer muses that maybe it's time to forgive Emily. Dusty is not pleased. Katie hides Simon when Mike returns to their room. Katie makes up a reason for Mike to take off again, then tells Simon she wants him to leave her and Mike alone. Later, Simon shows up with Vienna at the Kasnoffs' dinner table. Lucy supports a grieving Lucinda at Lily's bedside. Lucinda sees Jade at the hospital and assumes she's trying to worm her way back into the family. Jade denies, but later sneaks into Lily's room. To a comatose Lily, Jade admits how much she wished Lily were her mom. Gwen passes by and hears Jade crying. Gwen admits she knows what it's like to be all alone in the world.
On the cruise, Mike is amazed to see Simon is Vienna's boyfriend and takes a swing at him. Katie acts surprised, too, but Mike begins to realize that Katie already knew that Simon was on board. She takes Mike back to their cabin and explains to him about the massage, saying she hid Simon in the bathroom when Mike came back because she knew how upset he'd be if he saw Simon. Katie tells Mike she does not have any feelings for Simon any more, and he says he realizes that, that he's not jealous or insecure; it's just that Simon is bad news. Katie tells him she knows that now, that years ago, she wanted a fairy tale with Simon, but now she wants a real man in a real life and that she loves Mike more than she's ever loved anyone before. They kiss.
Meanwhile, Simon tells Vienna that Katie was his wife, and she asks if she was the "one who got away." Simon says yes, but Vienna tells him all that matters is the present. She strips to her undergarments, but as she and Simon kiss, she begins to feel seasick and has to go to the bathroom. Simon asks if she wants motion sickness pills, and she says later, when she can keep them down, so he leaves to go to the bar.
Katie tells Mike she's starving, since they never ate dinner, and that she's going to the bar to get a bottle of champagne and all the hors d'oeuvres she can carry. When she walks into the bar, she sees Simon, who has picked up a guitar and is playing a song.
Back in Oakdale, Gwen takes Jade to Carly's place, explaining why she and Will are staying there, and she offers to let Jade stay there, too. Jade is reluctant to take her up on the offer, but Gwen convinces her to go upstairs and at least take a nice hot shower, which they both do. Afterward, Jade apologizes to Gwen for the mistakes she made when she was trying to help Will with school, and Gwen tells her she forgives her. Gwen asks her about seeing Lily at the hospital, but Jade says she can't talk about that. The doorbell rings, and Gwen goes upstairs to get money for the pizza, asking Jade to answer the door. It's Will, who is angry to see Jade standing there in pajamas. Jade tells Will that she's not after him, that Gwen asked her to stay after finding out from Will that she was homeless since she lost her job at the library. Gwen comes outside and asks Jade to check out the boys' bedroom, where she can sleep; after Jade goes in, Gwen asks Will what he's so upset about. Will says he doesn't want Jade anywhere near them; Gwen says she thought Will wanted her, Casey, and Maddie to give Jade a break and try to help her. She says she's forgiven both Will and Jade for the whole school cheating thing, so unless there's something else going on, Jade should at least spend the night. Will agrees. Jade comes down and offers to leave, but Will says it's okay if she stays.
Dusty and Jennifer are in Bob's office, still talking about Emily. Jenn leaves as Paul comes in; Paul tells Dusty he's there to help him. Paul tries to convince Dusty to let him handle Emily, but Dusty tells Paul, "no deal."
Susan brings Daniel in to visit Emily, telling her that Tom and Margo are taking him on a short vacation and wanted her to say goodbye before they left. They hug and talk, and Jennifer walks in and watches them, sympathizing with Emily's desire to see her son. When Daniel says he heard his mom had done something good, Jennifer tells him that she did. Jennifer tells Emily that she's a good mother, and then she leaves. Emily tells her mom that maybe Jennifer is starting to feel empathy for Emily, and Susan agrees.
At Tom and Margo's house, they are getting ready to leave for their trip to Chicago, and Casey tries to hurry them out the door when Maddie arrives, which makes Tom and Margo suspicious. Maddie covers by saying she was bringing Casey his work hours at Crash, then she leaves, but Margo and Tom tell Casey now they're concerned about leaving him home alone for the next few days. Margo reminds Casey that Maddie is a minor. He tells them he's learned his lesson from his experience with Gwen and that he'll act responsibly from now on; somehow, this convinces Tom and Margo that it's okay to leave, so they depart. Casey calls Maddie and tells her to wait 30 minutes before coming back over. When someone knocks on the door, Casey opens it, expecting to see Maddie, but instead, it's a young man who tells him his name is Dallas Griffin and that he's looking for Margo. Casey says she's out of town for a few days, and Dallas turns to leave. He literally runs into Maddie, who looks at him with recognition, and Dallas says, "Maddie! It's been a long time."
Jennifer goes back to Bob's office and tells Paul and Dusty that Emily has begun to make amends. Paul says Emily is a loose cannon, and Dusty says she's a dangerous woman. Tom shows up, looking for his dad while Margo goes to get Daniel; Jennifer asks him when Emily's sentencing hearing is, saying she might want to put in a good word for Emily because of what she's done for Johnny. Tom tells her it will be after he returns to town, and then he leaves. Jennifer begs Dusty to reconsider pressing charges against Emily, telling him that keeping her from her son is not the way to help her get better. He tells her that he loves her and Johnny, but there's no way he's going to let Emily go free. Jennifer is very distraught, and then she faints into Dusty's arms.