Margo takes a call at the cop shop for Hal and realizes that he is still investigating her brother, Craig. Hal walks in with a pile of files on Craig and Margo confronts him. Hal tells her that he and Jack have dug up a lot of bad stuff on Craig and everyone still thinks that he is a good guy. Margo continues to argue and tells Hal that it is Christmas and he should lighten up. Hal asks her if because it is Christmas, are the cops supposed to stop chasing the bad guys? Hal tells Margo that he only has two weeks to prove to Barbara that Craig is not a good guy. Margo looks at Hal with a question on her face. Hal tells her that Barbara had said that after the holiday they were going to split. Margo suggests to Hal that maybe he should spend more time with Barbara and less time trying to put her brother behind bars. Margo leaves and Tom tells Hal that Margo is a good person and good sister. Hal says that he realizes that and he knows that she is on her way to talk to Craig.
Carly stops by the Munson's to pick up Parker and Jennifer tells her that he is still napping. While they are waiting on Parker to wake up, Carly can tell that Jennifer needs to talk to someone and she gets Jennifer to open up. Jennifer asks Carly how a good girl competes with all the bad girls in the world. Carly says, "Oh honey, have you come to the right place." Jennifer tells her about Bryant and the pressure that she is getting to have sex with him. She goes on to tell about Ruby, who is waiting in the wings to go to bed with Bryant at any time. Carly tells her to listen to herself and to not let Ruby play games with her and Bryant. She also says that if Bryant is worth it, he will wait on her. Jennifer says that she is still scared that she will lose him if she doesn't do what he wants. Carly tells her that she is a smart kid and she believes that she will make the right choice. Parker wakes up and Carly gets him and puts his coat on. Jennifer tells Carly that she is a good mom and her mom has given her good advice, she just never said it like Carly did. Carly says that if she was her daughter, she would be preaching about safe sex and Barbara has her best interest at heart. Carly tells Jennifer not to let any man make her his doormat, well except this one, and she points to Parker. They hug and Jennifer thanks her again and Carly leaves with Parker.
Craig has summoned Isaac to his hotel suite and Isaac is not happy. Isaac informs him that he is running a club and Craig is only an investor. He tells Craig that he has the club running in the black and it usually takes a business two years to run in the black. Craig tells him that he has asked him to his suite to inform him that he has noticed that he is keeping company with the Oakdale police. Isaac informs him that he can't stop a cop from stopping in after work to have a drink before going home. Craig says that he feels that Jack is not just stopping in for the fine scotch that they serve. Isaac gets upset with Craig and tells him that he will not take the fall for anything that Craig has done. Craig says that the bottom line is that the goods that Isaac has in his safe that belongs to him had better not have a scratch on it and he will have a buyer soon. Craig asks if his intentions are understood? Isaac says that they are heard loud and clear and Craig had better have heard his intentions also. Isaac leaves. Later, Carly comes home with Parker and Craig informs her that they have a buyer for the microchips. Carly wants to hear the details. Craig tells her that they will meet in Jake McKinnon's apartment. Carly asks him if he is crazy? She starts to make excuses why they can't meet there and there is a knock at the door. Craig motions for Carly to take Parker and herself out of the room. Carly and Parker leave and Craig opens the door. Margo is there and Craig says, "Happy holidays, sis!" Margo replies, "Bah, humbug and all that." Craig says that she is her old chipper self, he sees. She says that she is there to invite him to a family gathering. Their momma is coming to town and they are gathering to meet Katie's new husband. Craig is shocked and surprised and Margo gives him the scant details. Margo also warns Craig to not even jay walk in front of Hal. She tells him that Hal's Christmas wish is to see Craig behind bars.
At Java Underground, Bryant and Ruby are talking about his mother. He is telling his mother's story about growing up in Montega, coming to America to find her rich mother and then returning to Montega to fight for the people. As they are talking, a waitress comes up to Bryant and is all upset about one of her patrons. She tells Bryant that the woman has lost a very expensive bracelet and is blaming her for stealing it. Bryant says that he will take care of it. He goes over to the table and an older woman and a younger man is sitting there. The woman tells Bryant that she had on an expensive bracelet that is worth thousands of dollars and now it is missing and she feels someone has stolen it. Her son rolls his eyes at Bryant and tells his mother that the clasp was loose and it probably fell off somewhere. The mother starts to cry and says that her son always treats her like she is stupid. The son gets up and goes over to Bryant and tells him not to waste his time looking. He says that he will take his mother back to the hotel that they are staying in and if he should come across it, he can call them. The man gets his mother and takes her out of the club. Bryant starts to look for the bracelet. Ruby walks over and Bryant tells her about the woman and her bracelet. Isaac walks into the club and throws a fit about Bryant not being behind the bar. Bryant tries to explain about the woman and Isaac yells at him to get behind the bar. Bryant goes and Isaac picks up the phone and calls Jack. Jack is not home and Isaac says that he does not like leaving this on his recorder, so he will make it very short and to the point. He says that he can't help Jack anymore and that Jack should not even come to the club ever again. Isaac slams down the phone and looks up at Bryant, who is watching his boss. Bryant looks away. Ruby walks up to Bryant behind the bar and Bryant says that she should leave. He adds that his boss is back and he is not in a good mood and neither is Bryant. Ruby says that she thinks that she can make his mood better. She opens her purse and pulls out a diamond bracelet and holds it up in front of Bryant.
Katie has stopped in to see Craig and Margo is there. Margo makes a quick exit, but not before asking Craig to get Katie to come to her house for a family Christmas gathering and bring her new husband. After Margo is gone, Craig tells Katie that Margo has told him about her marriage. Katie tells Craig that she should have known that Margo couldn't keep her mouth shut and let her tell her news first. She tells Craig that she and Simon would like to take a honeymoon, but they have no money. She asks Craig if he will lend her a couple of thousand for the trip. Craig makes her a deal. He will give her one thousand dollars to come to a family get-together for the holidays at Margo's house. And, by the way, their mother will be there too. Finally, Katie gives in, but makes Craig promise that her family will not interrogate her new husband. Craig agrees and Katie leaves.
Lily is walking through the park with shopping bags of presents for Christmas. She stops at a Christmas tree and closes her eyes. She starts to make a wish and she opens her eyes and Simon is standing in front of her. She gasps and then they go to a park bench and act like they are not talking to each other. Simon explains that anybody could be watching them. He tells Lily that Katie thinks they should go away for a honeymoon. Lily says that she probably has sex in mind. Simon says that there will be no sex, only to get to know each other, so when the INS questions them, they know a little about each other. Lily is reluctant, but she agrees that it is probably a good idea. Simon tells her that he will spend the rest of his life making this up to her. He leaves and she goes to the tree to finish her wish. She wishes for this whole mess to be over with.
At the garage, Katie is decorating the place and Simon comes home. She tells Simon about the deal that she made with Craig. At first Simon says that he will not go to her family's house and be questioned relentlessly. Katie tells him that she made Craig promise to leave him alone and they need the money to go on the trip. Finally, Simon agrees and Katie is so happy she grabs him and kisses him. He pushes her away and says, "Katie!?" She apologizes and says that she is just excited about the trip. She says, "It is going to be the best holiday ever, baby!"
At Java Underground, Ruby is showing Bryant the bracelet. He tells her that they will have to return it to the old lady. Ruby says that she is going to keep it. She tells him that in the morning she is going to a jeweler and get it appraised. Bryant remembers that the old lady said that it is worth tens of thousands of dollars. Bryant offers to buy the bracelet from Ruby. He offers her three hundred dollars. She tells him no way, it has to be worth more than that, even if it is a fake. She tells him that she wants fifteen hundred dollars. He says that he does not have that kind of money. A waitress comes up and opens the cash register and Bryant gets an idea. He tells Ruby that there may be a way. She puts her arms around him and says that the first time she met him, that is what he told her. They start kissing and Jennifer walks into the club. She walks half way across the club and then sees Bryant and Ruby kissing. Before they see her, she leaves in tears. Bryant tells Ruby to go sit at a table and he will get the money. Ruby walks away and Bryant goes behind the bar and to the cash register. He opens the register and starts to dig into the money. A waitress comes up and says that she is leaving. He shuts the register and says that he will handle things from here. After she is gone, he opens the register again and takes out some money. He sneaks the money into his pocket and walks over to Ruby. He slides the money across the table to her. She takes the money and says that the boy has come through. She takes out the bracelet to hand it to him. He reaches for the bracelet and she snatches it back. She asks him if he is pulling a fast one on her. He says that he isn't. Before she gives him the bracelet she says that they must kiss to seal the deal. They kiss and she hands the bracelet over and walks out of the club.
Jennifer walks into her house and slams her purse down on the table. She is upset about Bryant and she says that Carly was right. The phone rings and Bryant is calling her. She is not happy to hear from him. He asks her to meet him at the old mill. She asks why? He says that he has something to show her. She says that she has something for him too. He asks for a hint. She says that it is something he has been waiting a long time for.
Lily takes a dim view of Rose and Lucinda's Christmas cheer. Bryant is uneasy when Jennifer comes on to him and is all the more surprised when she slaps him and tells him to go to Ruby if sex is all he wants. Jennifer then rips into him for kissing Ruby at Java Underground. Bryant shows her the bracelet he bought off Ruby and tells her they're going to be rich.
Joe shows Nancy the letter that accompanied Rose's diamond and worrying that Rose will be out for revenge, he tries to burn it, but his lighter won't work. Rose tells Lily of her plans to throw a Christmas/birthday party for Lucinda as thanks for all she's done for her, but an angry Lily refuses to participate. Jennifer is dismayed when she learns Bryant took $1500 from the Underground's till to pay Ruby and worries that the bracelet could be junk. Nonsense, Bryant insists--he knows quality.
After Rose guilt-trips her, Lily agrees to talk to Lucinda. Rose belatedly introduces Lily to her father. Alone, Joe shows Rose the letter, but begs her not to let it ruin her life. Rose reads the letter from her grandmother Caroline Carpenter and exults when she sees in the accompanying records that she was the firstborn--she has a case.
Lucinda can't help but laugh when Lily informs her that Simon avoided deportation by marrying Katie, and Simon did it at Lily's insistence. Lily caustically thanks Lucinda for raising her--she's now turned into a carbon copy of her. Jennifer rejects Bryant's plan to repay Isaac by selling the bracelet to a jeweler--they need to find the woman who lost it and maybe get a reward for turning it in.
Lily tells Lucinda that the era of "Holden and Lily" may be over and asks her to accept that Simon is part of her life. Lucinda then asks for a truce so they can gather the family and celebrate Christmas together, but Lily can't guarantee that Holden will be there. Jennifer agrees to contact a jeweler friend of her mother's about selling the bracelet after Bryant insists he must have the money back in the cash register by noon the next day, when Isaac will count it.
Lily comes upon Rose and Joe wrestling for control of Caroline Carpenter's papers and is surprised when Rose hands her her Christmas present--Rose and Lucinda's presents are coming later, Lily promises. Ruby holds a stack of bracelets in her lap as she rides out of Oakdale and boasts to her cohorts that Bryant is going to get "creamed."
Bryant and Jen find out the bracelet is a fraud and worth only about $20.00. Jen and Bryant tried to figure out a way to get the $1500.00 back to Isaac before he knew it was gone. Isaac however realized the money was gone but doesn't know who took it. Later, Jen asks Hal what the punishment is for stealing money from your employer. Hal tells her the usual sentence two to five years in jail.
Hal and Jack talked about getting the goods on Craig and Hal figures the only way to get anything is through Carly however, Jack doesn't want any part of it. Julia goes to Java to ask Isaac about Jack. She wanted to check out the suspicions Carly gave her about him. Jack later shows up looking for the microchips which have mysteriously disappeared. after returning home to find Carly asleep he tells Hal that Isaac is out and the microchips are gone. Julia wakes up and they watch the ultrasound of their new baby.
Barbara told a shocked Julia that her marriage to Hal was over. Julia begged Barbara not to rush into a divorce, but Barbara insisted that their marriage was beyond saving. Barbara was angry when Julia accused her of sacrificing her marriage for Craig Montgomery, but she softened when Julia confessed her insecurities about her own marriage to Jack.
Hal and Jack wondered how Craig was able to get the microchips out of the Java Underground safe without their knowledge. Jack balked at Hal's suggestion that they use Carly to bring Craig down and refused to work with her.
Craig gave a reluctant Carly last minute instructions about the microchip exchange and then dropped by the police station to see Hal and Jack. Craig accused the Oakdale P.D. of harassment and after a bit of verbal sparring, he assured them of his innocence and advised them not to believe anything Isaac Jenkins may have told them. Hal taunted Craig about their knowledge of the microchips and told him they would do anything to prove his guilt, including assigning cops to tail him around the clock. Craig threatened to sue the Oakdale P.D. if he was harassed any further. After Craig left, Hal ordered Jack to call Carly as she was their last resort.
Molly felt uncomfortable making out with Jake because of Vicky's presence. An old acquaintance of Jake's, Cindy Harrison from Bay City, dropped by unexpectedly to pay her respects to Jake about Vicky. Jake angrily questioned Cindy's reasons for coming since she and Vicky had been enemies and she had hurt the both of them many times. Just then, Carly dropped by on the pretext of visiting Molly, but in actuality she was meeting Cindy to make the microchip exchange. When Jake and Molly left the room, Carly gave Cindy the microchips. Suddenly Vicky appeared (Molly was the only one who could see her) and started yelling various accusations at Cindy. She then grabbed Molly's hand and made her spill coffee on a stunned Cindy. Cindy was further shocked when Molly began naming (with Vicky's help) Cindy's various grievances and left their apartment a little freaked out. Molly was thrilled when Jake begrudgingly admitted that he finally believed her about seeing Vicky and they decided to spend the night at a hotel.