Donna's grandmother is hospitalized after telling Donna that her soulmate is David, who moves out of the Valerie's room at the Walsh house and into Carly's vacant house until he can afford a more inexpensive place. Meanwhile, Kelly alerts Brandon to a potential story about a recently paroled ex-con who explains to Brandon about the mistakes he made that changed his life, which Brandon realizes parallel his own. Steve coaxes Brandon into a double date with two women who he ran into at the Peach Pit, unaware that the women are not who they appear to be. Valerie brings a record executive to the After Dark to hear David and the band, Jasper's Legend, perform their debut. But Valerie is hurt after David tells her that the love song he wrote was about Donna, not her.

Gina's visiting, self-serving mother, Bobbi, is little help when Gina learns that her trust fund isn't as large as she thought due to her mother stealing from it. Meanwhile, Kelly enlists Dylan's help for a trip to Mexico to help out Matt and Lauren to smuggle medicine for her into the country where Dylan and Kelly's romantic feelings for each other surface once again. But then Lauren thinks that her medication is not worth it and decides to re-commit herself back to the asylum in New York. Back in Los Angeles, Janet tells Steve that her father objects to her relationship with him since he is not Japanese. Also, Donna agrees to go out on a date with David as a distraction from her thoughts about Noah, who eventually learns about her and David's Valentines Day tryst from Gina.

Steve and Janet finally break the news of her pregnancy, which garners hostility from her conservative mother and father, and mixed reactions from his unorthodox father, Rush. Meanwhile, David tries to curb his radio persona in an attempt to make up with Robyn, but is sidetracked by fans wanting more of his love life. Both Matt and Noah offer to move out of the house to make room for Steve and Janet's nursery. Also, Dylan tries to help out a hotel maid who has to bring her two wild sons to work with her. Gina proposes a plan to Noah, to turn the After Dark into a gentlemen's club to make some quick cash.

As Christmas approaches, Gina's meeting with Dr. Martin as her biological father is awkward and unsatisfying, similar to 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, offers to help Gina financially, but she refuses. 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.