Air date: 11/17/99
Kelly finally learns from Mel that Gina had blackmailed him over his infidelity. But when Kelly tells David, he refuses to believe her or anyone thanks to his renewed involvement with Gina and her denials. At the same time, Kelly's mother, Jackie, asks Matt to represent her in suing David's father, while their daughter, Erin, shows obvious signs of depression over the breakup. Meanwhile, Dylan goes to bat for Andrew when the bigoted community center head tries to indirectly fire Andrew for being gay. But Dylan's victory over the center is bittersweet when word of Andrew's homosexuality spreads among the kids in which they no longer want Andrew around. Kelly also has to deal with Noah's presence in the beach front apartment which takes up space. Also, Steve and Janet's honeymoon is plagued by a series of mishaps and situations one of which includes a loud polka bank playing in the room next to theirs.
What's In a Name – Pt. 2
Air date: 11/17/99
Janet goes into premature labor near the end of the honeymoon and gives birth to a baby girl, while Steve maintains a vigil through the week as he worries about the safety of Janet and their newborn. Meanwhile, Dylan asks Kelly and Nat to volunteer in a feed the homeless Thanksgiving dinner at the community center. Kelly, seeking a way to get Jackie's mood in a boost, asks her to help out with the dinner, while little Erin continues to mope around about her parents separation and Kelly finally convinces Jackie that she has to moderate her accurate views about what a jerk Mel is around Erin for the sake of Erin's feelings. Donna learns of a past indiscretion by her father with Gina's mother, which brings out revelations that could threaten to tear Donna's family apart and has her seeing Gina's life in a new light. Also, David becomes uncertain about where Gina stands with him over her breakup with Dylan.
Sibling Revelry
Air date: 12/15/99
Dylan gives an expensive painting to Kelly as a gift which disturbs Matt thinking that Dylan is trying to buy Kelly's affections again. Meanwhile, Donna finally tells Gina their whole story about that they are half sisters, which throws Gina into anger and frustration. But Donna learns that Noah hasn't told her all of his life story when he tells her that he never went to Harvard. After returning from the hospital, Steve becomes overprotective of baby Madeline. Also, David's jealousy surfaces again when Gina confides in Dylan instead of him with her personal troubles, and he tells her their relationship is over.
Nine Yolks Whipped Lightly
Air date: 12/22/99
As Christmas approaches, Gina's meeting with Dr. Martin as her biological father is awkward and unsatisfying, similar to that of Janet and her parents when they accidentally run into each other at a Christmas tree lot. Steve eventually confronts Janet's parents and tells them to stop acting cold towards her and him. Donna's mother, Felice, condescendingly tries to buy Gina off, and Gina tells her "No thanks". Meanwhile, Donna can't let go of Noah's accident years ago resulting in the death of his girlfriend which leads to her and him considering breaking up. Also, Dylan loses control in front of kids during a Christmas gathering at the community center when he punches a belligerent neighbor complaining about the center's residents hanging around his house. Matt takes advantage of a client's latest fee to buy Kelly an engagement ring and proposes marriage which she accepts. But Dylan confides in David about him still having strong feelings for Kelly.
Tainted Love
Air date: 1/12/00
The loss of a client's business puts Matt in financial straits because of the engagement ring he bough for Kelly which was paid for with the retainer. Gina tries to help Matt by asking Dylan for the $15,000 Matt owes, but Matt refuses the money because of his own pride and reliance, while he begins lying to Kelly about his financial problems. Meanwhile, Dylan grows uncomfortable about God-parenting to Kelly because of her engagement. David and others benefit from a man's crush on Donna whom she asks out on a date that flops. Also, Noah attempts to fight his loss over breaking up with Donna by hanging out with a pair of wild and crazy swingers, named Josie and her brother Shane, that come to the After Dark every night.