List of Caroline in the City episodes
The following is a list of episodes for the American television sitcom Caroline in the City, which ran from September 21, 1995, to April 26, 1999, on NBC.
Series overview
| Season | Episodes | Originally aired | |||
|---|---|---|---|---|---|
| First aired | Last aired | ||||
| 1 | 24 | September 21, 1995 | August 5, 1996 | ||
| 2 | 25 | September 17, 1996 | May 13, 1997 | ||
| 3 | 26 | September 22, 1997 | May 18, 1998 | ||
| 4 | 22 | September 21, 1998 | April 26, 1999 | ||
Season 1: 1995–1996
| No. in series |
No. in season |
Title | Directed by | Written by | Original air date |
|---|---|---|---|---|---|
| 1 | 1 | "The Pilot" | James Burrows | Dottie Dartland, Marco Pennette, Fred Barron | September 21, 1995 |
| Caroline hires Richard. He pretends to be her date in an effort to make Del jealous. | |||||
| 2 | 2 | "Caroline and the Mugger" | James Burrows | Dottie Dartland | September 28, 1995 |
| Richard is mugged. | |||||
| 3 | 3 | "Caroline and the Gay Art Show" | James Burrows | Ian Praiser | October 5, 1995 |
| Richard enters an art show, only to later discover that it is only for gay artists. | |||||
| 4 | 4 | "Caroline and the Bad Back" | James Burrows | Bill Prady | October 12, 1995 |
| Caroline injures her back and becomes high on painkillers. Richard and Del create a comic for her. | |||||
| 5 | 5 | "Caroline and the ATM" | Rod Daniel | Jennifer Glickman, Mark Wilding | October 19, 1995 |
| The ATM fails to give Caroline her money, but when she goes to the bank and they need to watch the video of the transaction, she's too embarrassed as she picked her nose on camera. | |||||
| 6 | 6 | "Caroline and the Folks" | James Burrows | Marco Pennette, Fred Barron | November 2, 1995 |
| Caroline goes to Remo's to meet Del's parents. Richard reaches his 30th birthday. Annie goes to his apartment. Jonathan Silverman makes a cameo appearance as Jonathan Eliot from The Single Guy. Matthew Perry makes a cameo as Chandler Bing from Friends. | |||||
| 7 | 7 | "Caroline and the Opera" | Tom Cherones | Carol Gary, Dottie Dartland, Fred Barron, Marco Pennette | November 9, 1995 |
| Caroline goes to see the Marriage of Figaro with an old friend from Wisconsin. Del becomes jealous and asks Richard to teach him about the opera. | |||||
| 8 | 8 | "Caroline and the Balloon" | Tom Cherones | Bill Prady | November 16, 1995 |
| Caroline gets her own balloon in the Macy's Thanksgiving Day Parade. Caroline, Richard, Del, and Annie are volunteer rope pullers. | |||||
| 9 | 9 | "Caroline and the Convict" | Rod Daniel | Rob Lotterstein, Ellen Idelson | December 7, 1995 |
| Annie dates Steven, an ex-convict. He burglarizes Caroline's apartment, and steals one of Richard's paintings. | |||||
| 10 | 10 | "Caroline and the Christmas Break" | James Burrows | Amy Cohen, Michelle Nader | December 14, 1995 |
| Del and Caroline plan a trip to Paris, but after opening his big mouth Caroline decides to break up with him. | |||||
| 11 | 11 | "Caroline and the Gift" | James Burrows | Bill Prady | January 4, 1996 |
| Caroline believes Del bought her an expensive gift, which turned out be much more modest than she thought. Richard paints a nude of a Mobster's girlfriend. Annie tries to find a man she met at a New Year's Eve party. | |||||
| 12 | 12 | "Caroline and the Married Man" | Tom Cherones | Wil Calhoun | January 11, 1996 |
| Richard sets Caroline up on a date in order to increase his chances of getting an art commission, but it backfires upon realizing that he is married. | |||||
| 13 | 13 | "Caroline and the Twenty-Eight-Pound Walleye" | Tom Cherones | Carol Gary, Ian Praiser | January 25, 1996 |
| Caroline returns to her hometown of Peshtigo, Wisconsin, where a park is dedicated to her. Her brother Chris steals the limelight away from her once again, however. | |||||
| 14 | 14 | "Caroline and the Watch" | James Burrows | Mark Wilding | February 1, 1996 |
| Caroline buys an antique desk on the way to the deli, and later finds a watch gift wrapped inside. She tracks down the old owners. | |||||
| 15 | 15 | "Caroline and the Bad Date" | Tom Cherones | Dottie Dartland, Bill Prady | February 15, 1996 |
| Annie convinces Caroline to ask out a man shopping for shirts at the mall. He turns out to be paranoid. She mets Del at Remo's and they sleep together. | |||||
| 16 | 16 | "Caroline and the Proposal" | James Burrows | Ian Praiser, Marco Pennette, Fred Barron | February 22, 1996 |
| Caroline decides whether or not to accept Del's marriage proposal. Remo and Annie tell her Richard has feeling for her. Richard visits a temp agency looking for work. | |||||
| 17 | 17 | "Caroline and the Kid" | Tom Cherones | Jay Scherick, Bill Masters, Wil Calhoun | March 14, 1996 |
| Caroline and Richard paint a devilish child's room. | |||||
| 18 | 18 | "Caroline and the Ex-Wife" | Tom Cherones | Michelle Nader, Amy Cohen | March 28, 1996 |
| Caroline and Del go to his cabin in Vermont, only to find his second ex-wife and her boyfriend. | |||||
| 19 | 19 | "Caroline and the Movie" | Tom Cherones | Bill Prady | April 4, 1996 |
| Caroline, Richard, and Annie are extras in a movie. | |||||
| 20 | 20 | "Caroline and the Cereal" | Pamela Fryman | Rob Lotterstein, Ellen Idelson, Amy Cohen, Michelle Nader, Ian Praiser | April 18, 1996 |
| Caroline gets her own cereal, but everything is ruined when Richard realizes that it looks like something else. | |||||
| 21 | 21 | "Caroline and Richard's Mom" | James Burrows | Charles Harper Yates, Dottie Dartland | April 25, 1996 |
| Richard's mother visits Caroline's apartment. | |||||
| 22 | 22 | "Caroline and the Bridesmaids" | Tom Cherones | Wil Calhoun, Bill Masters | May 9, 1996 |
| Annie does a sub-par job of being Caroline's maid of honor. | |||||
| 23 | 23 | "Caroline and the Wedding" | James Burrows | Bill Masters | May 16, 1996 |
| Caroline gets cold feet as her wedding nears. Meanwhile, Richard writes her a love letter and leaves it on a pile of thank you notes. Caroline never opens the letter, but Richard leaves New York believing she had and rejected him. | |||||
| 24 | 24 | "Caroline and the Condom" | James Burrows | Fred Barron, Marco Pennette | August 5, 1996 |
| A flashback show showing events from shortly after Richard was hired. The events of this episode are out of order from the first season finale and the second season premiere. | |||||
Season 2: 1996–1997
| No. in series |
No. in season |
Title | Directed by | Written by | Original air date |
|---|---|---|---|---|---|
| 25 | 1 | "Caroline and the Younger Man" | James Burrows | Fred Barron, Marco Pennette | September 17, 1996 |
| Richard fails to sell enough paintings to live in Paris and returns to New York. Caroline takes Salty to the vet. The episode ends with Caroline finding Richard as he's moving into his new apartment. | |||||
| 26 | 2 | "Caroline and the Letter" | Gordon Hunt | Cathy Ladman, Marco Pennette, Fred Barron | September 24, 1996 |
| Richard finds out that Caroline never read his love letter, and tries to retrieve it before anyone sees it. He visits the apartment of Caroline's pregnant friend Vicky, throws the box of thanks you notes out the window, and helps Caroline deliver Vicky's baby. Annie finds his love letter on the street, and at the end of the episode plans to show it Caroline. Richard convinces her otherwise, saying it would only cause needless pain. | |||||
| 27 | 3 | "Caroline and the Cat Dancer" | Michael Lembeck | Brian Hargrove, Jack Kenny | October 15, 1996 |
| Annie has back taxes due, and agrees to help an IRS agent played by David Hyde Pierce perform in Cats. | |||||
| 28 | 4 | "Caroline and the Guy Who Gets There Too Soon" | Gordon Hunt | Donald Todd | October 22, 1996 |
| Joe professes his love for Caroline. | |||||
| 29 | 5 | "Caroline and the Dreamers" | Gordon Hunt | Bill Prady | October 29, 1996 |
| Del starts his own greeting card company, Eagle Greeting Cards, and Caroline reluctantly joins. Meanwhile, Richard paints a mural in a shady part of town. | |||||
| 30 | 6 | "Caroline and the Nice Jewish Boy" | Will Mackenzie | Tom Leopold | November 12, 1996 |
| Caroline receives an award, but Joe refuses to attend the ceremony because one of the sponsors makes mink coats. After failing to find another date, Richard agrees to go with Caroline. Meanwhile, Del pretends to be Jewish to get a date. | |||||
| 31 | 7 | "Caroline and Victor/Victoria" | Howard Deutch | Bill Masters | November 19, 1996 |
| Annie tries out for Julie Andrews' understudy. | |||||
| 32 | 8 | "Caroline and the Comic" | Howard Deutch | Fred Barron, Marco Pennette | November 26, 1996 |
| Caroline goes to see Richard's father, a shoe salesman and former stand up comedian. Judd Hirsch guest stars. | |||||
| 33 | 9 | "Caroline and the Therapist" | Gordon Hunt | Tom Leopold | December 3, 1996 |
| Joe gives Caroline the phone number of a cat therapist, who determines that Salty's odd behavior is the result of being around Richard. Richard goes to see his 3rd grade teacher, who had told him he was bad with animals. | |||||
| 34 | 10 | "Caroline and the Red Sauce" | James Burrows | Bill Prady | December 10, 1996 |
| Annie's mother Angie (Candice Azzara) comes to visit, saying there are termites in her house. Caroline discovers there may be more to this than it seems. | |||||
| 35 | 11 | "Caroline and the Freight King" | Gordon Hunt | Donald Todd | December 17, 1996 |
| Caroline gets locked in the laundry room of her building with a homeless man. Del tries to get Richard to create greeting cards for him. Annie keeps finding the same $5 bill with the word 'Repent' on it. | |||||
| 36 | 12 | "Caroline and the Perfect Record" | Michael Zinberg | Dottie Dartland | January 7, 1997 |
| Annie's record of never having been stood up is broken. Meanwhile, Joe's ex-girlfriend Lisa comes back into town and moves back into his apartment (which was in Lisa's name), which makes Caroline determined to tell Joe to move out. | |||||
| 37 | 13 | "Caroline and the Singer" | Will Mackenzie | Brian Hargrove, Jack Kenny | January 14, 1997 |
| Annie's sister Donna (Mackenzie Phillips) is visiting and cannot come up with a new song to relaunch her career. After finding Richard's love letter to Caroline in Annie's diary, she wants to use it for the lyrics to her new song, to Richard's dismay. Meanwhile, Caroline is unable to find her black pumps, and returns to Joe's apartment in search of them. | |||||
| 38 | 14 | "Caroline and the Kept Man" | Andrew Tsao | Jeff Abugov | January 21, 1997 |
| Richard's work is exhibited in a country club, thanks to Del. A fan of his work decides to become his patron but requires him to give up his job with Caroline. | |||||
| 39 | 15 | "Caroline and the Long Shot" | Will Mackenzie | Dottie Dartland | February 11, 1997 |
| Richard has a chance to win $100,000 by making a 3 point shot at a Knicks game, but he's never played basketball before. | |||||
| 40 | 16 | "Caroline and the Dearly Departed" | James Burrows | Brian Hargrove, Jack Kenny | February 18, 1997 |
| Richard pretends to be dead to further his career. | |||||
| 41 | 17 | "Caroline and the Getaway" | James Burrows | Daniel Henriks | February 25, 1997 |
| Caroline and Annie go to a ski resort, vowing not to search for dates while there. Richard tries to date a woman who followed him from a bookstore. | |||||
| 42 | 18 | "Caroline and the Monkeys" | Andrew Tsao | Donald Todd | March 11, 1997 |
| A former classmate of Annie's comes to visit. | |||||
| 43 | 19 | "Caroline and the Buyer" | Will Mackenzie | Jeff Abugov | April 1, 1997 |
| Del tries to convince Bob Anderson, the owner of Card Village, to carry Caroline in the City cards. | |||||
| 44 | 20 | "Caroline and the New Neighbor" | Michael Zinberg | Christopher Fife | April 8, 1997 |
| Richard becomes an illegal taxi driver, while Caroline helps an elderly neighbor dispose of her husband's body. | |||||
| 45 | 21 | "Caroline and the Critics" | Will Mackenzie | Jack Kenny, Brian Hargove, Bill Prady, Tom Leopold, Dottie Dartland | April 15, 1997 |
| Unaware of why a small town in upper New York has decided to drop her comic strip, Caroline and Richard go on a road trip to find out, only to have their car break down. | |||||
| 46 | 22 | "Caroline and the Ombudsman" | Will Mackenzie | Bill Prady | April 22, 1997 |
| Caroline hires an ombudsman to talk to her super. | |||||
| 47 | 23 | "Caroline and the Bad Trip" | Michael Zinberg | Donald Todd | May 6, 1997 |
| Caroline goes on The Tonight Show with Jay Leno. Richard sees his long lost girlfriend Julia. | |||||
| 48 | 24 | "Caroline and Richard & Julia" | Will Mackenzie | Bill Masters | May 13, 1997 |
| Caroline pretends to be Richard's wife. Annie goes to LA to do a sitcom with Shadoe Stevens. Del tries to keep his business from going bankrupt. | |||||
| 49 | 25 | "Caroline and the Wayward Husband" | Will Mackenzie | Kim Friese | May 13, 1997 |
| Richard goes downstairs to get some aspirin, and ends up kissing Julia. Caroline catches them and reacts badly. Caroline leaves a message on Richard's answering machine, only to have Julia erase it. | |||||
Season 3: 1997–1998
| No. in series |
No. in season |
Title | Directed by | Written by | Original air date |
|---|---|---|---|---|---|
| 50 | 1 | "Caroline and the Reception" | James Burrows | Michael Sardo | September 22, 1997 |
| Caroline throws a wedding reception for Richard and Julia to prove that she is not jealous and is over Richard. | |||||
| 51 | 2 | "Caroline and the Kink" | James Burrows | Oliver Goldstick | September 29, 1997 |
| Richard objects to the clothes Julia is buying for him to wear. Caroline advises him to stand up to Julia, but this causes Julia to walk out on him. | |||||
| 52 | 3 | "Caroline and the Novelist" | Andrew Tsao | Jack Kenny, Brian Hargrove | October 6, 1997 |
| Caroline goes on a date with a novelist whose book she claims to have read, but hasn't. Julia gets a job as a waitress at Remo's to make extra money, but is terrible at it. | |||||
| 53 | 4 | "Caroline and the Free Cable" | Andrew Tsao | Nancy Steen | October 13, 1997 |
| Caroline discovers that the whole building has been getting free cable from a connector in her apartment that she has never paid for. She goes to the cable company to volunteer to pay for it, much to Annie's annoyance. | |||||
| 54 | 5 | "Caroline and the Blind Date" | Arlene Sanford | Michael Sardo | October 20, 1997 |
| Caroline is set up with Trevor (Robert Gant) on a blind date at Happy Garden, a Chinese restaurant, but Richard and Julia accompany them and Richard interrupts everything Caroline and Trevor say. | |||||
| 55 | 6 | "Caroline and the Egg" | Arlene Sanford | Nancy Steen | November 3, 1997 |
| Richard's predecessor comes into town and asks Caroline to be an egg donor for her. Richard believes that his job is at risk and goes all out to make sure Caroline doesn't replace him with his predecessor. | |||||
| 56 | 7 | "Caroline and the Desperate Cat" | Arlene Sanford | Michael Sardo, Oliver Goldstick | November 10, 1997 |
| Annie's old vocal coach comes to town to see Annie in Cats. Annie is desperate to get back into Cats so that her teacher will see her perform. | |||||
| 57 | 8 | "Caroline and the Cold Sesame Noodles" | James Burrows | Fred Barron, Marco Pennette | November 17, 1997 |
| Richard buys Julia a wedding ring which goes missing after Caroline receives some Chinese takeaway. The delivery boy gets fired and ends up sleeping on Caroline's couch. | |||||
| 58 | 9 | "Caroline and the Bitter Beast" | Shelley Jensen | Oliver Goldstick | November 24, 1997 |
| Caroline and Trevor start dating again, but Trevor's dog refuses to accept Caroline. Caroline attempts to bond with the dog. | |||||
| 59 | 10 | "Caroline and the Councilman" | James Burrows | Lester Lewis | December 1, 1997 |
| A councilman wants Caroline in the City to endorse his run for re-election, and also buys one of Richard's paintings. Caroline doesn't want to give a political endorsement, and Richard wants his painting back. | |||||
| 60 | 11 | "Caroline and the Used Car Salesman" | Josh Baerwald | Daniel Henriks | December 8, 1997 |
| Richard becomes a used car salesman to earn extra money to buy Christmas presents, but doesn't tell Caroline or Julia, leading both of them to believe he is having an affair. | |||||
| 61 | 12 | "Caroline and the Decanter" | Will Mackenzie | Jodie Mann Massimi, Deborah Zoe Dawson | December 15, 1997 |
| Caroline goes to Del's family's house for Christmas and brings a decanter as a gift for Del's mother, not realising that it was a gift from Del's mother in the first place. | |||||
| 62 | 13 | "Caroline and the Love That Dares Not Speak its Name" | James Burrows | Jack Kenny, Brian Hargrove | January 5, 1998 |
| Del and Charlie compete with Cassidy Greeting Cards at a greeting card convention and try to get Annie to help make their stall more attractive to customers. | |||||
| 63 | 14 | "Caroline and the Quiz Show" | Will Mackenzie | Lester Lewis | January 12, 1998 |
| Caroline is asked to go on a radio quiz show but has a fear of being put on the spot, so Julia tries to help. | |||||
| 64 | 15 | "Caroline and the Reluctant Father" | Peter Chakos | Jim Halkett | January 19, 1998 |
| Del meets up with an old one-night stand and finds out that he has a daughter. | |||||
| 65 | 16 | "Caroline and the Outer Limits" | Will Mackenzie | Don Rhymer | January 26, 1998 |
| Charlie narrates this episode, in which Caroline temporarily switches bodies with Julia and realises what Julia's life is like. | |||||
| 66 | 17 | "Caroline and the Toothbrush" | Will Mackenzie | Kevin McMurtry | February 2, 1998 |
| Trevor decides to leave a toothbrush at Caroline's house. Caroline struggles with the commitment that this implies, and Richard inadvertently interferes, putting Caroline and Trevor's relationship at risk. | |||||
| 67 | 18 | "Caroline and the Cabbie" | Will Mackenzie | Nancy Steen | March 9, 1998 |
| Caroline falls out with a rude cabbie and threatens to report him. Richard becomes addicted to the Internet. Meanwhile, Annie gets an appointment at a celebrity hairdresser's and Del and Charlie try to collect the remnants of cut celebrity hair so they can sell it. | |||||
| 68 | 19 | "Caroline and the Visit from Mom" | Peter Chakos | Phil Parasoul, Nora Lynch | March 16, 1998 |
| Richard goes on a gambling tour hoping to cash in on a free bus voucher without actually losing any money. Caroline's mother comes to visit and Annie is surprised by how well they get on, but Caroline reveals this is because they don't discuss any difficult subjects. | |||||
| 69 | 20 | "Caroline and the Little White Lies" | Ted Wass | Nancy Steen | April 6, 1998 |
| Del and Charlie pose as a gay couple to get cheaper health insurance, but the lie spirals out of control. | |||||
| 70 | 21 | "Caroline and the Killer Dad" | Will Mackenzie | Michael Sardo | April 13, 1998 |
| Caroline becomes convinced that Julia's dad is secretly trying to kill Richard. Meanwhile, Del changes a line in Caroline's cartoon without her knowledge but becomes alarmed after nobody thinks his new line is funny. | |||||
| 71 | 22 | "Caroline and the Sandwich" | Shelley Jensen | Christopher Fife | April 27, 1998 |
| A local deli renames a sandwich (previously named after Jo Anne Worley) to name it after Caroline in the City. This leads to a backlash against Caroline. Jo Anne and Caroline stage a feud to maximise the publicity. | |||||
| 72 | 23 | "Caroline and the Marriage Counselor: Part 1" | Shelley Jensen | Oliver Goldstick | May 4, 1998 |
| Julia and Richard go to a marriage counselor, who tells Richard to quit and then applies for Richard's job. | |||||
| 73 | 24 | "Caroline and the Marriage Counselor: Part 2" | Shelley Jensen | Oliver Goldstick | May 4, 1998 |
| Julia and Richard's marriage counselor starts work as Richard's replacement but finds that everyone still wants him to give them relationship advice. | |||||
| 74 | 25 | "Caroline and the Secret Bullfighter: Part 1" | Michael Zinberg | Gary Murphy, Neil Thompson | May 18, 1998 |
| Richard and Julia host a party before leaving on holiday to Spain. After José, a bullfighter invited to the party, evinces an interest in Julia, Annie and Caroline see him in the bedroom having sex with a woman they believe to be Julia. After attempting to hide this from Richard, Caroline inadvertently tells him. | |||||
| 75 | 26 | "Caroline and the Secret Bullfighter: Part 2" | Michael Zinberg | Michael Sardo | May 18, 1998 |
| Caroline realises that the woman she saw with José wasn't Julia, and flies to Spain to tell Richard. Trevor, who has just moved in with Caroline, isn't happy. Meanwhile, Del tries to impress a woman by helping her son with baseball. | |||||
Season 4: 1998–1999
| No. in series |
No. in season |
Title | Directed by | Written by | Original air date |
|---|---|---|---|---|---|
| 76 | 1 | "Caroline and the Guys in the Bathroom" | Ted Wass | Michael Sardo | September 21, 1998 |
| Caroline goes to the bathroom to brush her teeth before kissing Richard, and is plagued by self-doubt as she's haunted by her former crushes and boyfriends. Eagle Greeting Cards is taken over by a larger company. | |||||
| 77 | 2 | "Caroline and the Office" | Ted Wass | Gary Murphy, Neil Thompson | September 28, 1998 |
| Julia's father throws Richard out of his home and takes all his possessions, so Richard ends up sleeping in Caroline's new office, which Caroline refuses to work in. | |||||
| 78 | 3 | "Caroline and the Rotten Plum" | Ted Wass | Oliver Goldstick | October 5, 1998 |
| Caroline falls out with Plum, the new office manager, when she wants to get a table removed from her office. Meanwhile, Annie discovers from her mother that her yoga instructor has previously done porn. | |||||
| 79 | 4 | "Caroline and the Drycleaner" | Ted Wass | Jan Nash | October 12, 1998 |
| Annie gets fired from Cats and goes out with her drycleaner to help her self-esteem. Caroline is asked to watch a focus group on Caroline in the City cards and tries to incorporate their ideas. | |||||
| 80 | 5 | "Caroline and the First Date" | Ted Wass | Marcy Vosburgh | October 26, 1998 |
| Del is put in charge of the company's Halloween party but is concerned that the people in charge in previous years have always been fired soon afterwards. Richard and Caroline set up a first date but have very different ideas of what to do, and Richard ends up in an altercation with a headwaitress (Jane Lynch) at Caroline's favourite restaurant. | |||||
| 81 | 6 | "Caroline and the Paper Chase" | Ted Wass | Arlene Hellerman | November 2, 1998 |
| Caroline accidentally discovers Richard's divorce papers in his desk at work, which Annie then reads. Due to a series of mishaps the divorce papers end up in the company's internal mail and Caroline and Annie end up running around the building looking for them. | |||||
| 82 | 7 | "Caroline and the Big Night" | Howard Deutch | Tom Burkhard | November 9, 1998 |
| Caroline and Richard go away and book a B&B for the big night when they are finally planning to sleep together. When they arrive they find that their room has been double-booked but Caroline becomes obsessed with the idea of getting the room back. | |||||
| 83 | 8 | "Caroline and the Diva" | Howard Deutch | Jim Keily, Jimmy Aleck | November 16, 1998 |
| Caroline and Annie plan to go to a concert to see an opera singer perform, but Richard also wants to take Caroline. As a result all three of them end up going. Meanwhile, Del is told to instruct Reg, one of the other cartoonists, to incorporate a white character into his all-black comic strip, and is promised a chance at going to the company's executive retreat. | |||||
| 84 | 9 | "Caroline and the Booby Trap" | Ted Wass | Marcy Vosburgh | November 30, 1998 |
| Annie considers getting a breast enhancement after getting frustrated with her lack of success at auditions. Caroline starts considering one as well. | |||||
| 85 | 10 | "Caroline and the Bar Mitzvah" | Brent Carpenter | Jason Strouse | December 14, 1998 |
| Richard's aunt offers him $5,000 to have the bar mitzvah he never had. Caroline gets angry with Richard for compromising his principles. | |||||
| 86 | 11 | "Caroline and the Fright Before Christmas" | Ted Wass | Oliver Goldstick | December 21, 1998 |
| Caroline gets angry with Del, Annie and Richard for not getting into the Christmas spirit, so they take her to a Christmas village. | |||||
| 87 | 12 | "Caroline and the Big Bad Bed" | Ted Wass | Gary Murphy, Neil Thompson | January 11, 1999 |
| Richard refuses to allow Caroline to add a bath mat to his bathroom. Caroline's fellow cartoonist Reg gets thrown out of his house and ends up staying in Richard's apartment. Meanwhile, Del and Annie start going to the gym together to pick up potential dates, but Annie is more successful than Del is. | |||||
| 88 | 13 | "Caroline and the Horny Kid" | Ted Wass | Tom Burkhard | January 18, 1999 |
| Caroline starts mentoring a boy at work, but he develops a crush on her. | |||||
| 89 | 14 | "Caroline and the Firing Squad" | Shelley Jensen | Jimmy Aleck, Jim Keily | January 25, 1999 |
| Spurred on by Caroline, Charlie insists on having a bigger say at work and attends a board meeting, to Del's alarm. Based on a recommendation from Richard, Annie gets a job modelling for a handsome cartoonist (Scott Lowell) as a character called Queen Neptuna. | |||||
| 90 | 15 | "Caroline and Joanie and the Stick" | Ted Wass | Jason Strouse | Unaired |
| Joanie, Caroline's classmate from Peshtigo, unexpectedly shows up as Caroline and Richard are about to leave on holiday to Boston. Caroline tries to help her get her children's book published. Meanwhile, Del is insecure that his new girlfriend is taller than he is, and Annie babysits a parrot belonging to the guy from the mailroom at Caroline's office. This episode was not aired on NBC, but was included in the syndication package. | |||||
| 91 | 16 | "Caroline and the Ancestral Home" | Ted Wass | Jan Nash | March 15, 1999 |
| Caroline takes Del, Annie and Richard with her to go visit her parents in Peshtigo for their wedding anniversary, but pretends that she is still engaged to Del to please her grandmother. Caroline discovers that her childhood friend Randy has moved back to Peshtigo, which makes her think about whether she wants to stay in Manhattan forever or eventually move back to Peshtigo. | |||||
| 92 | 17 | "Caroline and the 2000th Strip" | Claudia Weill | David Moses, Shari Brooks | March 8, 1999 |
| Caroline is excited about attending a party to commemorate her 2000th trip but panics when she finds she can't think of a storyline for the strip. | |||||
| 93 | 18 | "Caroline and the Sudsy Guy" | Ted Wass | Tom Burkhard | March 22, 1999 |
| Caroline's grandmother refuses to move out of her family home in Peshtigo, so Caroline flies there to convince her. She runs into Randy again, who has to help her when the washing machine overflows with suds. In the meanwhile, Richard is left in charge of a sick Annie and has to advise Del on his love life. | |||||
| 94 | 19 | "Caroline and the Return of the Sudsy Guy" | Ted Wass | David Jay Willis, Stefanie Novik | March 29, 1999 |
| Richard is given an opportunity to have his work exhibited. Meanwhile Randy flies to New York for a conference and ends up spending a lot of time with Caroline. | |||||
| 95 | 20 | "Caroline and the Ultimatum" | Marco Pennette | Jan Nash, Oliver Goldstick | April 5, 1999 |
| Caroline feels her relationship is drifting and gives Richard an ultimatum. Richard gets involved in a video store robbery and ends up locked in a storeroom and unable to ring Caroline. | |||||
| 96 | 21 | "Caroline and El Niño" | Ted Wass | Gary Murphy, Neil Thompson | April 26, 1999 |
| Julia's lawyer sends Richard an unwelcome surprise in the post and he and Caroline decide to go to Italy to deal with it. | |||||
| 97 | 22 | "Caroline and the Big Move" | Ted Wass | Michael Sardo, Marco Pennette | April 26, 1999 |
| Richard ends up in Italy for six months and Caroline struggles without him. Meanwhile Randy shows up again and discovers that Annie and Del are sleeping together. This episode ends with an unresolved cliffhanger. | |||||
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