Donna and David meet promising new mates for themselves, she with an unpredictable businessman named Jerry, and he with a law clerk named Chrissy. Meanwhile, Kelly decides to quit working at the boutique store. Soon after being suspended by the state bar for misappropriate use of legal funds, Matt violates his suspension by taking a case of an injured factory worker, until Chrissy finds out and threatens him. The increasingly moody Dylan suffers from the fast-lane acquaintances of Noah's which takes a turn for the worse when both Dylan and Gina are arrested when Josie's stash of drugs is found in the limo they take for a drive. Also, Steve and Janet hire a nanny, named Darby, for baby Madeleine whom Noah asks out on a date.

Matt's older brother, Patrick, pays a visit with his wife and asks Matt for a very personal favor: to be a sperm donor so his wife can have a baby since he is sterile. But Kelly pressures Matt not to agree to the favor. Noah is threatened by Josie's brother, Shane, when Dylan refuses to cover for Josie's drug loss after David destroyed a drug stash to avoid getting arrested. Meanwhile, Steve tells Janet about his previous encounter with Darby who was a wild and crazy nymphomaniac during her days at college. Donna, now running the boutique shop on her own, goes out with a fashion designer, named Dan, while David has a meeting with Camille Desmond, a magazine columnist. Also, Gina gets a promotional job offer, but only if she trains her employer's spoiled son, Michael, for an upcoming prom dance contest his school is giving.