Lucinda persuades Holden to go with her to check out Lily's relationship with Keith. When they arrive at Lily and Holden's house, they find that Lily is out with Keith, and Lucinda finally persuades Holden that Keith might be a bad guy. Meanwhile, Lily is flying in a plane with Keith. Exhilarated by her first flying lesson, Lily kisses Keith. In the plane, Lily receives a call from Tom Hughes, and she and Keith land and go to the police station. There Tom tells them that bee pollen was found all over Les's car. Les protests that Keith is setting him up, and Keith wears a satisfied smile as he and Lily leave the station.
At the police station, Margo and Tom plan a fun evening of dancing to 50's music for the next evening. Margo asks for Lisa's help in getting all dolled up. Katie and Henry come by and Margo tells Katie about the sting and Craig's departure. Katie dashes out the door, telling a surprised Henry, "Meet me at metro in an hour." Katie goes straight to Mikes' to tell him that he should go get Jennifer now that Craig is gone. At the BRO office, Jennifer begins packing her Street Jeans belongings, but Dusty arrives to tell her that she and Worldwide are back in business because Craig has left the country. Jen's reaction surprises Dusty - she walks out the door and goes directly to Mike's house. When Jennifer arrives, Katie slips out the door after hearing Jennifer propose to Mike. Mike accepts and Jennifer goes back to BRO to tell Dusty that she is ready to get to work. There is a definite chemistry between Jen and Dusty. Katie and Henry celebrate that Jen and Mike are together.
Alison returns from visiting Aaron in Seattle to find that her apartment has been broken into, with the window standing open. Aaron is lurking around when Hal mentions that they will dust the windowsill for fingerprints. Will nervously leaves to take Alison to Metro to take care of some business. At metro, Alison tells Casey and Celia about the break-in, and they remember finding Will inside Alison's apartment while Alison was gone. When Celia starts asking questions about Will, Casey orders her to stay out of it. After they return to Alison's apartment from metro, Will puts his arm around Alison to comfort her.
Henry tries to convince Katie to tell him where Craig has gone. but she tries to tell him that she can't tell him because she doesn't know. He gives up on that, but then he tries to get her to agree to tell Mike and Jennifer that Craig found out about the baby's due date from her. Henry believes it is the kind of secret that can come back and hurt her in the future and she must tell it as soon as possible. He finally convinces her, and a reluctant Katie asks him to come along.
Jennifer has had quite an active day. First she finds out that Craig is gone, then she and Mike get back together and now she learns from Dusty that Street Jeans is back in business! Dusty isn't sure she can handle all the pressure with a baby on the way, but Jennifer assures him she can. As Jennifer leaves the Street Jeans office, she runs into Barbara. Jennifer is actually nice to her as they talk about Craig's "eviction" from Oakdale. Barbara admits to having had a hand in it and says she'd do anything for Jennifer, who is very grateful. They hug! But Jennifer starts to feel sharp, stabbing pains in her tummy and is worried about the baby. Barbara whisks her off to see Dr. Schilling.
Henry and Katie are surprised to see Mike is such a great mood. He tells them he knows they are there to try to get him and Jennifer back together again, but that they are too late. He grins ear to ear as he tells them that Jennifer and he are getting married. Katie is very relieved. She chickens out regarding telling him the truth about how Craig found he was the baby's father and they leave. Mike checks the messages on his cell phone and hears the message from Jennifer. He panics and gets to the doctor's office just in time to hear the baby is fine, that what Jennifer is experiencing is totally normal. Both Mike and Jennifer ask Barbara to stay when Jennifer has an ultrasound and can see the baby. Barbara leaves them gracefully, thanking them for letting her stay. Dr. Schiller overhears Mike and Jennifer talking about Katie and Henry, and she mentions that Katie was very interested in knowing about the baby and when it was due. They put two and two together and quickly realize that Craig found out about the baby from Katie.
When Lily and Keith return from the police station and their airplane ride, he very bluntly tells her that he wants to be more than friends with her. Lily obviously likes him, but she tells him that she is a little scared as it has been a long time since anything like this has happened. Holden drops the girls off from their trip to the petting zoo but does not come into the house because he saw Keith's car. As Lily goes to get their lunch, Keith examines a piece of very expensive crystal in the living room. When she returns, he asks her to join him for dinner at the Lakeview that evening. She accepts happily.
Meanwhile, Lucinda has been doing some digging. She is very concerned about Keith and just doesn't trust him. She talks with Les about why Keith would want his sister dead. Les tells her about J.J.'s trust fund and that if he, Les, is in jail, Keith stands to get about half a million dollars. Les tells her that if Keith could kill his own sister for money, no telling what he might do to Lily!
Lily is very unhappy to see Lucinda show up at her house. Lucinda calls Keith a murderer and Lily tells her that she has gone too far and stomps out to join Keith on their date.
Keith, however, has a visitor. A visitor he is not very happy to see. The man knocks on Keith's door and asks to be let in. Clearly, it is someone he knows..... Just as Lily is turning the corner to Keith's room, she overhears their conversation: "I took care of her, I did what you asked, and now I want my money!"
Katie was trying hard to convince Henry that she did not mean to tell Craig about Jennifer's pregnancy. Henry still believed that Katie should tell Mike and Jennifer the truth, that she was the one who told Craig about the baby. After much talking Henry convinced Katie, and they both went off to tell Mike and Jennifer together what happened. Meanwhile, at the hospital Mike and Jennifer had just put two and two together and realized that Katie was the one that told Craig about the baby. Katie was at Mike and Jennifer's place when they came home from the hospital. Mike told Katie that they figured out that it was her that told Craig about the baby. Katie tried to apologize and explain what had happened, but Mike did not want to hear it. Mike called Katie a liar and told her to leave. Katie and Jennifer were left alone when Jennifer blasted Katie, accusing her of still being in love with Mike. Katie denied her feelings for Mike, but Jennifer told her that she did not believe Katie. Jennifer said that her and Mike were happy and that Katie could never break them up no matter what schemes she pulled.
Lily interrupted a conversation between Keith and some man who claimed that he took care of what Keith wanted, and now he expected to get paid for it. Keith covered for the mysterious man, and told Lily that he was a friend of his named Joe from school. Keith walked Joe out and as Joe was leaving he told Keith he was giving him 24 hours to give him the money. Lily and Keith went to Metro where Lily was visibly upset about what she had just overheard. Lily finally admitted to Keith that she heard what they were talking about and wanted to know what was going on. Keith told Lily that Joe paid off Keith's landlord in Chicago for him and that he owed him money. Lily was happy to find out that Keith let go of his apartment in Chicago. In the meantime Lucinda showed Holden a document stating that Keith tried to take money out of JJ's trust fund the day Julia died. Holden still did not fully believe that that would be reason enough for Keith to murder his own sister. Having nothing more to say, Holden left and went to Metro for some drinks where he saw Lily and Keith. Keith left the table after receiving a call from JJ and Holden went over to talk to Lily. Holden started to give Lily the third degree because Lily did not know Keith, and that she should be careful and take things slow. Lily reminded Holden that he did not take things slow with Julia and told him to back off. Seeing that he was getting no where with Lily he told her to ask Keith what Keith was doing the day Julia died regarding JJ's trust fund and left, leaving Lily uneasy.
Celia told Casey that she did not trust Will and that she thought that Will was the one that trashed Alison's apartment. Casey said that Will would never hurt Alison like that, and told her not to tell Alison that Will was in her apartment while she was away. Margo showed up to talk to Casey and Celia left to find an outfit for the dance. Margo told Casey that she was nervous about the dance the next night, and that she needed to start getting ready so she could look wonderful for Tom.
Will was at Alison's trying to make her feel safe because she was still scared about the break in. Celia showed up and told Will to tell Alison that he was in her apartment, but Will refused and told her to keep her mouth shut. After Celia left, Alison asked Will to spend the night and sleep on the floor so she could feel safe.
Dusty called Jennifer to tell her he had scheduled a press conference in two hours. Jennifer made an excuse but Dusty wouldn't take no for an answer. Mike was concerned that Jennifer was taking on too much but she assured him that she was doing just fine and she would appease Dusty for a week or two. Jennifer casually slipped in that she and Mike should get a justice of the peace and get married. Mike said no because he wanted to have a wedding. Jennifer was surprised Mike wanted a big wedding. Jennifer thought they should seize the moment because she was afraid something would jinx them. Mike said that they could wait and do it right. Meanwhile, Barbara surprised Dusty because she wanted to be at the press conference to support Jennifer. Dusty told her to get lost. Barbara refused to leave and asked Dusty what he was afraid of. Dusty fears that Jennifer will up and leave again because she is not very dependable. The press started to arrive and no sign of Jennifer. She was too busy planning her wedding with Mike. Dusty kept the press busy by fielding questions. When Dusty got stuck on a question, Jennifer walked in and answered for him. After some of the press left, Jennifer apologized but Dusty said to save it.
Alison woke Will from a sound sleep and thanked him for staying with her. Will bent over backwards to do whatever he could for her including getting her breakfast. As Will left, Celia was coming to see Alison and was concerned to see him leaving. Celia came in and found out Will had spent the night. Celia finally told Alison about the break in. Alison was shocked. Over at the Lakeview, Casey caught up with Will and asked him if he told Alison about leaving the window open. Will said no but he would tell her later. When Will went back to Alison's, she asked him how he could do lie her and slammed the door in his face!
Keith arrived at Lily's and asked her to the fifties dance but when he noticed that Lily was distant, he asked what was wrong. Lily wanted to know about JJ's trust fund. She told him that Holden was asking about the fund. Keith figured it was Lucinda who was behind the accusations. Lily told him that her family was just concerned and apologized to Keith. Keith said it was time to tell her the complete truth. Keith told her about being in debt and that he was going to borrow money from the fund and pay it back when he started working again. Lily forgave him and believed that he would be true to his word and pay the trust fund back. Lily offered Keith the use of her grandfather's house and he gladly accepted. After Lily left the room, Keith smiled to himself.
Lisa gave Holden a big hug when he arrived at the Lakeview. Holden was waiting for Faith to arrive so he could take her to see a movie. Lisa asked why he didn't go to the house to pick Faith up. Holden replied that he wasn't going to the house because of Keith. Lisa was quick to say that Keith hadn't paid his hotel bill. Holden thought that Keith was in debt and Lisa said it made sense that Keith was spending time with Lily. Holden asked Lisa if he could get into Keith's room. Lisa made an excuse that it would be unethical to do so but conveniently left the master key on the counter and walked away. Holden got into the room but was quickly interrupted by Keith's accomplice who was there to search the room. Holden escaped unnoticed and reported it to Lisa. Lisa told Holden to tell Lily before it was too late. Faith arrived and told Holden that Uncle Keith was moving into great-grandpa's house!
Jennifer tells Mike that she blew it with the press conference; Barbara arrives and says she's calling a family conference and has asked Paul to come over. He arrives, and Barbara says they are there to help Jennifer juggle all her responsibilities. Jennifer explains to Paul about what happened at the press conference, and Paul asks her to let him and/or Barbara help her with Street Jeans. She keeps insisting she can handle it, but between the wedding plans and Street Jeans and the pregnancy, they all realize that something's got to give. Barbara begs Jennifer to let her handle planning the wedding and designing the wedding gown, and ultimately persuades Jennifer that this is a good idea, which makes Barbara quite happy.
At Alison's apartment, Will tries to get Alison to talk to him so he can explain what happened when her apartment was robbed. Ultimately, he prevails, and he learns that she thinks he is the one who trashed her apartment. He asks if Celia told her this, and then he tells her what really happened. Alison wonders how the perfume bottle got broken and realizes Will had been smelling the perfume to remind him of her. Will blurts out that he loves her, then tries to cover it by saying she is a good friend to him. Alison tells Will she can't continue to be his friend because it involves too much worrying and too much responsibility, and she can't keep hurting him over and over every time she has to remind him that she loves Aaron.
Devastated, Will leaves Ali's apartment and tries to call Jennifer, leaving her a message saying he'll stop by her place since he can't reach her by phone. When he arrives at the cottage, he sees the "Congratulations" banner that Katie had made for Mike and Jennifer lying on the porch, and he wonders what the congratulations are for. Peeking in the window, he sees Barbara and Jennifer and overhears them talking about the pregnancy and the wedding. Then Mike and Paul come into the room, and Will hears Paul offer a toast, "To my new brother. Welcome to the family!" Will leaves, and Jennifer hears a noise outside but doesn't know who it was. Later, she suddenly realizes they haven't told Will about the pregnancy and wedding yet, but Mike says that since Jennifer's tired, it can wait until the morning.
Will goes to the rooftop of a tall building and thinks about what he has just been through with Alison and what he overheard at Jennifer's place. He drops his cell phone over the edge of the building and then begins walking on the ledge of the building, balancing precariously.
Casey and Celia arrive at Yo's for the 1950s party. Casey tries several times to call Will on his cell phone, but Celia keeps trying to prevent him from doing so. They see two of the girls from school who have been giving Celia a hard time, and Celia kisses Casey to try to make them jealous. After several aborted attempts to reach Will on the phone, Casey calls Alison, who tells him that she and Will are no longer friends, and that if he wants to know why, he should ask Celia. When Celia walks up, Casey tells her he knows that she told Alison about Will being in her apartment while she was gone; he realizes that Celia thinks Will actually trashed Alison's apartment himself, even though she had no proof of this, and that this is what she told Alison. They fight, with the two high school girls watching gleefully, and Celia leaves.
Margo and Tom arrive at Yo's. Keith and Lily also arrive, although Lily briefly has cold feet about actually going inside and being seen in public on a date with Keith. They run into Tom and Margo almost immediately.
Jack meets Holden for what he thinks will be a "guy's night out," saying that since Carly is in Montana and the kids are with a sitter, he has the night off. Holden asks what Jack knows about Keith, mentioning the man he saw with a gun in Keith's room who was talking about money that Keith owed him, and tells Jack about Lucinda's suspicions about Keith being after JJ's money and Lily's money. Holden asks Jack to talk to Lily about "our concerns." They go back to Lily's house, with Holden carrying a sleepy Faith, only to find a babysitter there. The sitter explains that Lily has gone out for the evening, and after she carries Faith off to bed, Holden tells Jack that Lily must be with Keith, so this is their opportunity to go through the guest house to see what they can find out about him. Jack convinces Holden that this would not be a good idea.
Jack takes Holden to Yo's, thinking they can shoot some pool, but when they walk in and see the 1950s party going on, they start to leave. Holden spots Lily and Keith and marches up to them and tells Lily he has to talk to her. He tells Lily that Keith is a deadbeat who hasn't paid his hotel bill and owes a guy some money, and that this guy was at the hotel with a gun telling someone about the money Keith owes him. Keith explains that the man, Joe, is an old friend from his service days and from his piloting career, and he even shows Holden the man's picture. Lily says she knows all about the situation; she wonders if Holden has been eavesdropping. Jack gets Holden to leave, and he apologizes to Keith and Lily for interrupting their evening.
Jack takes Holden elsewhere and asks him if he's jealous of Keith. Holden says perhaps on a knee-jerk level, but that he's mostly worried that Keith might be dangerous and that he's around the kids. Jack says Holden needs to be sure about this, because if he is still in love with Lily, it's a whole different ball game.
Tom and Margo win the dance contest. Keith goes outside for a breath of fresh air, where he is promptly punched in the face by Joe, who wants to know what Lily would think if she found out just how far Keith would go for money.