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19 Episodes 1999 - 2000
Episode 1
Sun, Sep 26, 1999 60 mins
Sparks fly between Jacqueline "Jack" Barrett and David "Jill" Jillefksy when they meet in New York---after she leaves her unfaithful fiancé and his girlfriend asks him to move in with her. Meanwhile, Jack (Amanda Peet) applies for a job at the TV station where Jill's girlfriend works. Jill: Ivan Sergei. Elisa: Sarah Paulson. Audrey: Jaime Pressly. Barto: Justin Kirk. Mikey: Simon Rex.
Episode 2
Sun, Oct 3, 1999 60 mins
Jack is stunned and Jill is fearful when Jack's ex-fiancé (Vincent Ventresca) finds her and asks for another chance. As Jack agonizes, Jill tells a lie to prevent the reunion. Meanwhile, Mikey pushes his way into Barto's apartment to fill the opening Jill created when he moved in with Elisa; and Jill has to retrieve an important toy prototype he borrowed from the office or risk losing his job.
Episode 3
Sun, Oct 10, 1999 60 mins
Jack wades cautiously back into the dating pool when she follows advice from Audrey (Jamie Pressly) to have a meaningless fling. Meanwhile, Jill decides to meet more women by throwing a party, but then complicates matters when he invites Elisa and Jack. Elisa: Sarah Paulson.
Episode 4
Sun, Oct 17, 1999 60 mins
Jill's boss (Bill Macy) taps him for a promotion but dies before he can make it official, and Jack is assigned an undercover story checking for health-code violations at a restaurant. Meanwhile, Audrey reconsiders dumping her boyfriend when she learns he can get her a juicy stage role, and Mikey feels down because he has no career goals.
Episode 5
Sun, Oct 24, 1999 60 mins
Jill's chance meeting with a former classmate (Monet Mazur) becomes an intimate encounter, and Jack and Elisa's friendship is strained as Elisa confronts the truth about Jack and Jill's feelings for each other. Meanwhile, Barto (Justin Kirk) finally gets a chance to make an impression on Audrey (Jamie Pressly) when he supports her through an anxiety attack over the demands of her new stage role. Travis: Timothy Omundson. Mikey: Simon Rex.
Episode 6
Sun, Nov 7, 1999 60 mins
Jill is rattled when his kid sister Abby (Virginya Keehne) comes to town for a college interview and is nothing like he remembered; and Barto and Audrey finally connect when Audrey laments Travis's failure to pay her enough attention. Meanwhile, Elisa gets a sweet surprise when she goes solo for a night on the town. Barto: Justin Kirk. Elisa: Sarah Paulson. Travis: Timothy Omundson.
Episode 7
Sun, Nov 14, 1999 60 mins
Jill finally decides to ask Jack out---but she's already swooning over a sexy new reporter (Josh Hopkins). Meanwhile, Barto's relationship with Audrey is distracting him from his studies and he plans to tell her how he feels. Elsewhere, Mikey (Simon Rex) follows Elisa (Sarah Paulson) to a support group gathering for singles in hopes of meeting some eligible women. Jack: Amanda Peet. Jill: Ivan Sergei. Audrey: Jaime Pressly. Barto: Justin Kirk.
Episode 8
Sun, Nov 21, 1999 60 mins
When a co-worker (Sean O'Bryan) takes credit for his idea, Jill challenges him to a boxing match that becomes a story assignment for Matt (Josh Hopkins) and Jack. Meanwhile, Barto's pursuit of Audrey (Jaime Pressly) hits another obstacle when she begins flirting with an influential theatrical agent; and Elisa rhapsodizes over a mystery man (Chad Willett). Jack: Amanda Peet. Jill: Ivan Sergei.
Episode 9
Sun, Dec 19, 1999 60 mins
Jill is sued for breaking up a marriage and Jack begins to doubt her relationship with Matt (Josh Hopkins) when Jill insinuates that Jack may not be the only lady in Matt's life. Meanwhile, Audrey (Jamie Pressly) frets when Barto (Justin Kirk) starts hanging out with a female study buddy; Elisa continues the hunt for her mystery man; and Mikey (Simon Rex) gets a unwanted promotion that requires him to fire one of the waitresses. Elisa: Sarah Paulson. Jack: Amanda Peet. Jill: Ivan Sergei.
Episode 10
Sun, Jan 9, 2000 60 mins
Jill's suspicions are aroused when he sees Matt with another woman, and he contemplates telling Jack. Meanwhile, Jill's tactless girlfriend (Lori Rom) offends Mikey; Elisa inadvertently sees her boss naked; and Audrey becomes intimidated by Barto's medical expertise. Jill: Ivan Sergei. Jack: Amanda Peet. Mikey: Simon Rex.
Episode 11
Sun, Jan 16, 2000 60 mins
Barto takes Audrey to meet his snobbish parents (Jessica Walter and Stephen Macht) after she overhears his mother's invitation on the answering machine. Meanwhile, Elisa finally gets to meet her mystery man (Chad Willett), and Jack and Jill get stuck in the laundry room, ruining their dates with Matt and Allison. Matt: Josh Hopkins. Allison: Lori Rom. Barto: Justin Kirk.
Episode 12
Sun, Jan 23, 2000 60 mins
When she finds an unusual item in Jonathon's closet, Elisa suspects he has another woman. Meanwhile, Jill's career takes off when one of his prototypes is put on the fast track, while an unexpected money crunch forces Jack to take a second job at the bar. Ice Cream Man: Michael J. Pollard. Botel: Vito D'Ambrosio. Jeff Gerard: Andy Buckley. Allison: Lori Rom.
Episode 13
Sun, Feb 6, 2000 60 mins
Part 1 of two. As Jack ponders Jill's passionate declaration of his feelings for her, she learns Matt (Josh Hopkins) has gotten an offer for a job in Washington, D.C., and has snared an interview for her as well. Meanwhile, Jill continues job hunting and pursuing Jack; Mikey tries to prove he can handle a committed relationship; and Elisa and Jonathon clash over the issue of his late wife. Belinda: Caryn Greenhut. Lucy: Angela Featherstone.
Episode 14
Sun, Feb 13, 2000 60 mins
Conclusion. Jack chooses between Jill and Matt; and Elisa swears to Jonathon (Chad Willett) that she doesn't want anything for Valentine's Day. Meanwhile, Audrey injures her leg and Mikey stubbornly continues his attempt at commitment with Belinda (Caryn Greenhut), despite being drawn to Lucy (Angela Featherstone). Jack: Amanda Peet. Jill: Ivan Sergei. Matt: Josh Hopkins.
Episode 15
Sun, Feb 20, 2000 60 mins
Relationships become strained as Jack and Jill realize they're revealing too much about their love lives to their best friends, Audrey and Barto. Meanwhile, Jack and Elisa clash as Elisa keeps giving Jack too much information about former boyfriend Jill's personality and Mikey goes apartment hunting. Lucy: Angela Featherstone. Audrey: Jaime Pressly. Barto: Justin Kirk. Mikey: Simon Rex.
Episode 16
Sun, Feb 27, 2000 60 mins
New roommates Mikey and Elisa clash when she becomes too chummy with one of Mikey's dates (Elizabeth Berkley). Meanwhile, Jack and Jill spar over saying "I love you," and Audrey worries about her relationship with Barto when he seems to prefer sleep to sex. Elisa: Sarah Paulson. Audrey: Jaime Pressly. Mikey: Simon Rex.
Episode 17
Sun, Mar 5, 2000 60 mins
Barto starts seeing the ghost (Tom Bosley) of his med school cadaver after he tries and fails to save a bystander suffering a heart attack, Jill asks Jack to pose nude as homework for his photography class, and Jonathon becomes jealous of Mikey for living with Elisa.
Episode 18
Sun, Mar 12, 2000 60 mins
After Jack and Jill exchange apartment keys, Barto catches Jack in her boyfriend's room reading Jill's private journal. Meanwhile, Audrey is up for a role in a movie, and Mikey and Elisa complain to their friends about each other's faults as roommates. Barto: Justin Kirk. Audrey: Jaime Pressly. Mikey: Simon Rex.
Episode 19
Sun, Mar 19, 2000 60 mins
Audrey's agent (Randy Becker) stokes her infatuation with Hollywood, leaving Barto feeling neglected and vulnerable to sympathy from Annie (Elisa Donovan). Meanwhile, Jack and Jill consider moving in together during Audrey's impending sojourn in Los Angeles and Barto's temporary relocation to North Carolina for a research fellowship. And Mikey romances a film star with exotic tastes.