Jake is visited by an old girlfriend, Colleen, who stuns him with the news that he is the father of her four-and-a-half-year-old son. She asks Jake to waive his parental rights so that her husband can adopt the boy. Jake is furious that Colleen failed to tell him the truth, and considers starting a custody battle. He believes that caring for a son could give him the direction he is lacking in his life. Jake becomes angry because Jo believes it might be best to let the boy stay with a stable family. Jake ultimately decides that it is in David's best interests to stay with Colleen and her husband, and signs away the rights. Jo secretly takes a photo of Jake with his son as a memento. Alison learns that she needs surgery to remove a benign tumor from her uterus. If she doesn't have the surgery, she may not be able to have children. However, she has no way to pay for the operation because she has no insurance. Billy becomes very frustrated with the ever-present bureaucracy at ever

Alison undergoes successful surgery, and Billy agrees to care for her when she returns home from the hospital. They both become frightened by how much they have come to care about each other. Jake and Jo observe that the necklace Billy plans to give Alison for Christmas is more than a ""friendship"" present. Billy disagrees, but decides not to give Alison the gift after she makes him agree to a ""no presents"" pact (because she is short on cash). Alison fears that she has hurt Billy's feelings. She later apologizes, and he gives her the necklace. They admit that they have become confused by their feelings. Jo and Jake try to overcome their unhappy memories of Christmas. He is excited about making a fresh start, but she remains cynical and wants to ignore the holiday. She also tries to push Jake away, but they end up having a hot make-out session. Michael is depressed when he and Kimberly cannot save a young gunshot victim, but his spirits are revived after delivering a baby for t

Jane receives a surprise visit from her sister Sydney, who has dropped out of college. Jane keeps the news from their parents, but is annoyed when Syd hangs around her workplace. Kay eventually hires Sydney as her assistant. Billy agrees to set up Alison with one of his friends, as she needs a date to the advertisers' ball. He scuttles the whole thing due to jealousy, and agrees to be Alison's date to make it up to her. Jake buys a new motorcycle and tries to convince Jo to take his old bike. She hesitates because she fears becoming indebted to a man. Jake tries to prove himself by taking up one of Jo's interests, poetry. He tells her that he has gained a lot from knowing her, and that he only wants to see her happy. Jo is disturbed when she is repeatedly contacted by her husband, whom Jake later finds snooping around the mailboxes. Rhonda is furious when Terrence doesn't defend her honor to his snobbish friends, but he later proposes marriage.

Sydney continues to get on Jane's nerves. Jane tells Michael that she is going to kick Sydney out of the apartment, but Michael has already asked Syd to take Jane out and get her to a surprise birthday party. He convinces Jane to go out with Sydney and think things over. This proves to be a disaster, as they get into an argument. Jane accuses Syd of trying to steal her life, and Sydney lets her storm out instead of taking her to the party. Michael has to spoil the surprise to get Jane to the event. Jane orders Sydney to move out, and the two talk about their long-standing differences. Jake reluctantly tells Jo about his meeting with her husband, Charles. Jo decides to contact Charles. Jake feels helpless when Jo begins seeing Charles, who seems to be a changed man. Jake later admits his strong feelings for Jo and shares his frustation about standing on the sidelines. Charles shows his ugly side after drinking, and grants Jo a divorce. Jo thanks Jake for his patience, and he

Alison is promoted to junior account executive and works with art director Amanda Woodward on an underwear account. Alison flirts with the handsome tennis star who is modeling for the account. She decides not to pursue him because she fears it could affect her career. Jo is hired as photographer, but jeopardizes the account with her ""alternative"" photos. Alison gets into hot water when she takes a risk and shows the client Jo's photos, even though they had already expressed approval about the more traditional shots. Jo upsets Jake and Alison by going to dinner with Rex. She later apologizes to Jake and admits that she has strong feelings for him. Billy doesn't hit it off with a blind date arranged by Michael, but is attracted to Amanda. An overwhelmed Rhonda breaks her engagement after Terrence tries to buy them a house in the suburbs.

Amanda, Billy and Alison spend the weekend at a lakeside cabin. Alison is concerned by Billy and Amanda's obvious attraction. She asks Billy not to date Amanda, as a break-up could hurt Alison's career. They decide to see each other behind her back, but Amanda later comes clean. Alison becomes angry with Billy for sharing her concerns with Amanda. She grows lonely and tries unsuccessfully to call Keith. Jake and Jo have a romantic evening and consummate their relationship. After spending the weekend together, they avoid one another because they are worried about the direction of the relationship. They agree to just relax and take things as they come. Matt is caught in the middle of Rhonda and Terrence's romantic problems. The couple gets back together, but decides to take it slow.

Alison remains irritated about Billy's relationship with Amanda. Amanda suggests that Alison might have feelings for Billy, and recommends that the two discuss their relationship. Alison begins to consider this possibility, and Billy agrees to meet with her. Someone sends flowers to Alison at work and asks her to meet him at Shooters that night. She assumes that the flowers are from Billy (creating problems for Billy and Amanda), but is instead approached by a newly divorced Keith. She agrees to give their relationship another try, so long as they take things slowly. Alison and Keith have a disastrous dinner with Billy and Amanda. Billy goes home with Amanda and sleeps with her. Jo's husband offers her a $50,000 divorce settlement, but she wants to turn it down because of her pride. Jake feels that this is a foolish decision from someone who doesn't know what it's like to be poor. Jake loses his job when the repair shop goes out of business. He believes that he could take ov

Billy backs out of plans with Alison to have dinner with Amanda and her father. Amanda's father declares that Billy is a worthless bum. Keith loans Alison his sports car, but she has it stolen at gunpoint. He comforts her when Billy isn't home to hear her tearful messages. Billy feels guilty about not being there for Alison. Amanda suspects that Billy is in love with Alison. He tries to disprove this by moving in with Amanda. Keith and Alison renew their relationship. She asks him to move in with her, but he later receives an unexpected job offer. Keith asks Alison to move to Seattle with him. Jake objects to ""silent partner"" Jo's attempts to help with the business. Jo takes Alison to the shooting range to try to help her overcome her fears about the carjacking, but Alison is horrified by the fact that Jo owns a gun. Jo mentions this to Jake, who is equally appalled. Jo promises to get rid of her gun. Jake apologizes for being stubborn and asks Jo to be his full partner and do

Billy's father dies of a heart attack. Amanda tries to exploit Billy's vulnerable state to seduce him, and then shows up at the funeral in an attempt to score points with her ex. Alison flies back from Seattle to comfort Billy. Billy feels that he let his father down, and decides to take over the furniture store. His mother says that she has sold the store to the employees, and that she wants Billy to use his writing gifts. She gives Billy a letter in which his father expressed his pride in him. Billy drives Alison to the airport, but she decides to move back to Los Angeles. Michael tries to convince Kimberly to move in with Billy, but she declines. She explains that seeing the death of his father reminded her of how much involvement she would have in his life if they were roommates. Michael lies about going to the hospital and instead helps Kimberly with a plumbing problem. She offers him dinner and tries to come on to him, but he resists. Billy's family tragedy prompts Matt to

The apartment building goes up for sale. Lucy resigns from D&D, and tells Amanda and Alison that promotions may be in their future. Amanda asks Alison to keep her pregnancy under wraps, but Alison lets it slip while out drinking with a colleague to make Billy jealous. Amanda denies the man's allegations. She later suffers a miscarriage while working late with Alison. Billy and Amanda grow closer as he consoles her, and he is torn between the two women. An unidentified individual begins harassing Alison. Keith returns to Los Angeles, completely obsessed with Alison. Michael and Jane rekindle their romance during a weekend getaway. Jo tries to dodge Jake's discussions of commitment. She is arrested for carrying a concealed weapon while working on a photo essay about the homeless. Jake is enraged to learn that she went back on her promise to get rid of the gun. Rhonda proposes to Terrence. Keith stakes out Alison's apartment, and attacks Billy from behind with a tire iron. While Billy is