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.

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.

A revenge-seeking Shane and his friend Carl, kidnap Noah and then send a ransom e-mail to Dylan for his release. Dylan agrees to deliver the ransom money without notifying the police, but confides in Steve about the situation. Then Dylan is waylaid by Josie and Shane who plan to kill him and Noah anyway. Meanwhile, Kelly and Matt prepare to go on a couples Valentine's Day game show with Donna and Janet as their coaches. But when Kelly has an attack of nerves, Donna goes on the show with Matt in her place. Donna's father tries to bond with Gina who continues to be uncertain about what to do. Also, David continues his growing relationship with Camille, until the arrival of an ex-boyfriend which puts a form of jealousy and fear in David.