#1 Pilot #2 Dysfunction Junction #3 Guess Who's Chumming for Dinner #4 Stormy Heather #5 Frisky Business #6 Bad Will Hunting #7 Torn Between Two Mothers
Chandler returns home to the Williams family to find that his father is marrying his ex-lover. Jenny falls off the wagon after she finds out her boyfriend is married. Peter tries to prevent his father's new wife from getting too much control.
Heather still pines for Chandler even after she marries his father. Richard taking her to Hawaii for their honeymoon doesn't help squash her memories of his son. Heather plans to have Chandler's baby and pass it off as Richard's. Peter tries to prevent Heather from receiving the company that Richard wants to give her as a wedding present: Dress2K.com. The whole family sees Heather as a threat except for Chandler who just wants to support his father. Jack, Richard's brother and Gwen's best friend, shows up to help the family celebrate Richard's marriage. He brings with him David O'Connor, a new manager for Laurie and Jenny's nightclub, Pulse. Chandler and Samantha share a steamy kiss.
With some prompting from Scott, Chandler tries to start something with Samantha, however when Heather finds out Chandler and Samantha have a date she seduces Chandler. Ethan, Gwen's late sister's teenage son, gets dropped on Gwen's doorstep after his abusive father abandons him. Samantha becomes Heather's top executive at Dress2K and advises her to throw a family dinner party to get the Williamses on her side. Heather uses Ethan's arrival as an excuse for a dinner party, but the whole thing ends in disaster. Jenny and David are flirting, but Laurie tells David that Jenny is an alcoholic and to leave her alone. Jenny thinks she's ruined her chances with David after he catches her trying to sneak a drink at he family dinner but then she sees him at an AA meeting.
David tells Jenny that two alcoholics shouldn't get involved and breaks up with her. Just when Laurie is starting to admit that she might have a crush on David, she sees Jenny seducing him. Peter starts to catch on that Heather has a thing for Chandler. Chandler pushes Heather away, but then cancels his date with Samantha anyway. Heather tells Peter that Samantha is on the rebound and Peter manages to get Samantha to go out with him. Samantha starts to see Peter in a different light. When Heather faints at the Dress2K premiere, Chandler takes her to a doctor friend of his. He softens towards her when he hears his baby's heartbeat for the first time. Heather brings up kids to Richard and Richard shoots her down. Chandler says that since Heather hasn't told Richard about her pregnancy yet, Chandler will have to do it. Richard makes sure Gwen gets the money she needs to renovate the Williams resorts, but doesn't let Heather know about it. Ethan gets into Benchley, the private school that all the Williams kids attended.
Jenny does a spectacular job making a presentation to potential Australian investors, but falls back into her alcoholism as well. Oddly enough, it's Ethan that helps her. Sexual tension grows between David and Laurie even though David and Jenny have been sleeping together. Chandler considers returning to the Navy, but his father fights him on it. Richard admits to Gwen that she is, and always has been, his best friend. Peter finally figures out about Heather and Chandler in Hawaii, and downloads security tapes from the Hawaiin resort. Using the tapes, he blackmails Heather into signing Dress2K away, and then gives control of the company to Samantha. When Chandler finds out about the blackmail, he wants to tell his father the truth, but before he can do so his father has a heart attack while in bed with Heather.
As the Williams family recovers from Richard's sudden death, Jack returns to take over the position of CEO. Laurie blows up at Jenny for always having to be the center attention after Jenny shows up to Richard's funeral drunk. Jenny moves in with David and they declare their love for each other. Samantha decides to take over Dress2K and she and Peter grow closer. Peter finds out Heather wasn't included in Richard's will and bribes her to leave town. Heather makes a last ditch effort at getting together with Chandler, but after she is rejected she decides to take Peter's offer. Just as she is about to leave she meets Richard's other lawyer who has a new version of the will. Richard's children, wife and ex-wife are now all equal partners. Peter tries to show the videotape of his brother's affair with his step-mother to his uncle Jack to prove that Heather is the enemy. When Jack isn't interested in playing Peter's games, Peter shows the tape to his mother who immediately confronts Heather and warns the second wife that she will be destroyed. Heather shoots back that she's pregnant with Richard's child.
The whole family finds out about Heather and Chandler's affair and the fact that Heather is pregnant with "Richard's baby." Gwen confronts Chandler about the true paternity of the baby and he backs up Heather's lie. Jack warns Chandler to stay away from Heather, but he finds it difficult. Chandler takes over an aviation project that his father was working on. Samantha start to fall hard for Peter until a pointer from Heather has her discovering many of his lies. David tries to slow things down with Jenny and Jenny moves back home, bringing a dependency on prescription pain-killers with her. As David and Laurie grow closer, Jenny spots them together and assumes an affair when they're only talking about Jenny's problems. Jack considers and offer for Williams Global and sexual tension grows between him and Gwen. Ethan spies on the pretty girl next door and is pleased when she becomes his new French tutor.
Sam, still rejecting Peter, saves the funding for Chandler's aviation project after Peter bungles it. Jenny suspects that David is having an affair with Laurie, and runs away from rehab after Jack and Laurie force her to go. While Jenny is sleeping it off at David's apartment, David and Laurie admit to each other that they do have feelings, and despite their guilt they share a kiss. Heather pretends to date a hunky doctor to make Chandler jealous, and it almost works, but instead Heather ends up falling down a flight of stairs. Ethan walks away from a fling with Faith after she exposes her wild side.
Although Jack and Laurie try to hide it from her, Gwen figures out that Jenny is doing drugs, and Jenny admits that she thinks it's her fault that her parents' marriage broke up. Laurie breaks off any possibility of a relationship with David as he continues the masquerade of being Jenny's boyfriend. Heather loses the baby from her fall down the steps and uses the sympathy from the family to reclaim some control of Dress2K. Although initially Chandler still feels manipulated, he and Heather end up bonding over their tragedy. Peter manipulates Samantha into bed. Jack toys with selling Gwen's hotel to a competitor, but ends up giving her an infusions of cash for marketing and renovations instead.
Jack admits his feelings to Gwen and they share a kiss. Gwen realizes that Faith is no good an forbids Ethan to see her, but when Gwen goes out of town Faith throws a party with Ethan at the house. Jenny gets David a promotion. David and Laurie finally give into their feelings and Jenny spots them together... in the shower. Jenny gets wasted and falls into the pool during Ethan and Faith's party. Heather finds out about Peter's scam with Maureen and blackmails him into giving her back control of Dress2K. Peter and Samantha get more serious and vow revenge on Heather. Chandler and Heather try to start their romance all over again.