Sam and Janeane arrange a dinner date for Jonathan with an annoying, self-absorbed executive (Olivia d'Abo).

Jonathan dates Sam's tennis instructor.

Jonathan agrees to babysit Matt and Janeane's eight-month-old son and discovers the baby is a "chick magnet."

Jonathan and Matt spend the day together and Jonathan mimics his friend's charitable endeavors.

Jonathan stays with his gay neighbors while his apartment goes through repairs.

Jonathan's girlfriend Tina is excited when he and his friends are robbed at gunpoint, which takes their relationship to new heights.

Ileana Douglas plays Janeane's opinionated older sister who comes to the city for Thanksgiving and Sam must fire a flaky employee.

Jonathan and Amanda's relationship is threatened by his interest in her flirtatious girlfriend.

Jonathan attempts to rekindle his relationship with a former girlfriend on New Year's Eve.

Jonathan pursues a French model; Matt and Janeane listen in on a neighbor's affair; and Sam shares an embarrassing washroom secret of Trudy's.

Trudy hosts a kleptomaniac artist (Rick Overton) who includes stolen items in his shows and Jonathan dates a wise beyond her years teenager.

Jonathan becomes romantically interested with Janeane's sister, Martha, who then moves to New York City for a job as a consultant to the mayor.

Conan O'Brien plays a literary rival of Jonathan as they compete for a quote from an acclaimed author with a penchant for poker and professional boxing.

Jonathan suspects Sam is developing more than a work relationship at the recording studio while Trudy is away in Budsoezt.

Jonathan plans a birthday party for Manny but it may be in jeopardy when the tenants vote to replace him with a high-tech surveillance system.

Attending the wedding of his first love Jonathan hides from the bride and meets Renee who's avoiding her ex, the groom.

Jonathan's friends are using his apartment as a love nest and he strategies as to how he can date a critic who thrashed his book