Season 2: 1996–1997
| Total | # | Title | Director | Writer(s) | Original air date |
|---|---|---|---|---|---|
| 25 | 1 | "Caroline and the Younger Man" | James Burrows | Fred Barron, Marco Pennette | September 17, 1996 (1996-09-17) |
| 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 (1996-09-24) |
| 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 (1996-10-15) |
| 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 (1996-10-22) |
| Joe professes his love for Caroline. | |||||
| 29 | 5 | "Caroline and the Dreamers" | Gordon Hunt | Bill Prady | October 29, 1996 (1996-10-29) |
| 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 (1996-11-12) |
| 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 (1996-11-19) |
| Annie tries out for Julie Andrews' understudy. | |||||
| 32 | 8 | "Caroline and the Comic" | Howard Deutch | Fred Barron, Marco Pennette | November 26, 1996 (1996-11-26) |
| 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 (1996-12-03) |
| 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 (1996-12-10) |
| 35 | 11 | "Caroline and the Freight King" | Gordon Hunt | Donald Todd | December 17, 1996 (1996-12-17) |
| 36 | 12 | "Caroline and the Perfect Record" | Michael Zinberg | Dottie Dartland | January 7, 1997 (1997-01-07) |
| Annie's record of never having been stood up is broken. | |||||
| 37 | 13 | "Caroline and the Singer" | Will Mackenzie | Brian Hargrove, Jack Kenny | January 14, 1997 (1997-01-14) |
| Annie's sister is visiting and can't 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 (1997-01-21) |
| 39 | 15 | "Caroline and the Long Shot" | Will Mackenzie | Dottie Dartland | February 11, 1997 (1997-02-11) |
| 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 (1997-02-18) |
| Richard pretends to be dead to further his career. | |||||
| 41 | 17 | "Caroline and the Getaway" | James Burrows | Daniel Henriks | February 25, 1997 (1997-02-25) |
| 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 (1997-03-11) |
| A former classmate of Annie's comes to visit. | |||||
| 43 | 19 | "Caroline and the Buyer" | Will Mackenzie | Jeff Abugov | April 1, 1997 (1997-04-01) |
| 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 (1997-04-08) |
| 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 (1997-04-15) |
| 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 (1997-04-22) |
| Caroline hires an ombudsman to talk to her super. | |||||
| 47 | 23 | "Caroline and the Bad Trip" | Michael Zinberg | Donald Todd | May 6, 1997 (1997-05-06) |
| Caroline goes on the 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 (1997-05-13) |
| 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 (1997-05-13) |
| 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. |
Read more about this topic: List Of Caroline In The City Episodes
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