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25 Episodes 1996 - 1997
Episode 1
Tue, Sep 17, 199622 mins
Season 2 starts three months later and Richard is in France painting pictures besides the Seine. However, he hasn't been successful and has to return home. He needs work and ends up in an ice-cream parlour. With Richard's people skills it isn't a great success. Salty is injured and Caroline ends up on a date with the vet, Joe, who is 7 years younger. Unfortunately, Joe is an animal liberationist and is busy releasing captive animals, which results in Caroline being arrested. She ends up in bed with him. The next morning there is serendipitous meeting with Richard.
Episode 2
Tue, Sep 24, 199622 mins
Richard finds out that Caroline didn't read the letter he left her so he conspires to get it back. He finds out that it is at Vicki's place. When Richard is there getting the letter, Vicki goes into labour and he helps with the birth.
Episode 3
Tue, Oct 15, 199622 mins
Caroline and Joe are getting on and Del is envious. Annie is audited by the IRS. When the auditor finds out she is in Cats he offers to go easy on her if Annie gets him an audition for Cats.

Episode 4
Tue, Oct 22, 199622 mins
Joe declares his love for Caroline, which stuns her and leaves her unsure about what to do. Richard inherits a car but has to admit that he can't drive. They all decide to help him get his licence.

Episode 5
Tue, Oct 29, 199622 mins
Del stands up to his father and ends up being fired. He decides to set up his own company and convinces Caroline to join him. Richard is commissioned to paint a mural in the South Bronx but the locals don't want it.
Episode 6
Tue, Nov 12, 199622 mins
Caroline has a party but her boyfriend refuses to attend cause the company sponsoring the thing uses animal products. So Caroline tries to find someone to escort her. Eventually Richard offers to take her despite, his having feelings for her. And Charlie takes Del to a Jewish mixer and meets a Jewish girl and hits it off with her. But doesn't tell her he's not Jewish.

Episode 7
Tue, Nov 19, 1996
Richard accompanies Caroline to the doctor, while there the doctor discovers that Richard has a polyp and says he needs surgery. Richard is so nervous that before his surgery and heavily medicated runs away from the hospital and goes to Caroline. Annie to get ready for an audition for Vitor/Victoria dresses up like a man.

Episode 8
Tue, Nov 26, 199630 mins
An old friend of Richard's father, Ben, appears. Ben was a struggling stand-up comedian and they now want him for a benefit. Richard has issues with his father so Caroline intervenes to get them together.

Episode 9
Tue, Dec 3, 199622 mins
When Caroline's cat starts acting oddly, Joe recommends that it should see a cat therapist. The therapist decides that Richard is the problem as he has issues with animals. Annie goes on a blind date organised by her mother.

Episode 10
Tue, Dec 10, 199622 mins
It's Christmas time and Caroline and Richard have different approaches to it. Annie's mother moves in with her because she has separated from her husband. Charlie hires a new secretary for Del. However, he hadn't checked out her past.
Episode 11
Tue, Dec 17, 199622 mins
Del hires an unsuccessful stripper-gram girl as a receptionist and Charlie is jealous. He also tries to convince Richard to draw some Christmas cards. Caroline is accidentally locked in her building's laundry overnight with a homeless man.

Episode 12
Tue, Jan 7, 199722 mins
Caroline's romance hits a snag when Joe's ex-girlfriend turns up and wants to move into his spare bedroom. Caroline decides to let him move in with her. Richard is given a large piece of marble to sculpt and stores it at Caroline's place.

Episode 13
Tue, Jan 14, 199722 mins
Annie's sister, Donna, is a singer and is visiting. She finds Richard's letter and wants to use it as inspiration for a new song. Caroline has left her black pumps at Joe's place but she is reluctant to go to his place since the break-up.

Episode 14
Tue, Jan 21, 199722 mins
Del arranges to exhibit one of Richard's paintings at his club. A wealthy woman there takes an interest in Richard, but not for his art. She wants him to quit working for Caroline. Caroline volunteers to read to the elderly.

Episode 15
Tue, Feb 11, 199721 mins
Richard and Caroline go to an NBA basketball match but he only goes to hear the singer of the national anthem. He wins the chance to win a $100 000 basketball three point throw. Unfortunately, Richard has no idea about how to do this.

Episode 16
Tue, Feb 18, 199721 mins
Richard is trying to get his artwork reviewed by a famous artist. To help sell one of his paintings Caroline says that he is dead. When she is successful, Richard decides to tell everyone that he is dead. Then, he has to have a funeral.

Episode 17
Tue, Feb 25, 199722 mins
After blowing off Caroline a few times, Annie decides to go with her on a girls' weekend to the snow. However, as neither can ski, they have to find something else to do, which means men. Richard dates a woman he met at a bookstore.

Episode 18
Tue, Mar 11, 199722 mins
For the first time, Caroline decides to go to a restaurant to dine alone and it doesn't go well. Then she goes solo to a movie. Del tries to date Annie's friend, who is a convicted pyromaniac. Charlie sees monkeys all over the city.

Episode 19
Tue, Apr 1, 199721 mins
Annie's mother is driving her crazy. Caroline finds out that some stores are no longer stocking her cards. Del works out a plan and takes the store owner out for a dinner with Caroline, but he misinterprets what she is offering.

Episode 20
Tue, Apr 8, 199722 mins
Caroline helps an elderly neighbour but the lady starts taking advantage of her. Things come to a head when she asks Caroline and Annie to help her take her naked dead husband to a funeral home.

Episode 21
Tue, Apr 15, 199722 mins
Caroline is obsessive about being liked by everyone and becomes upset when an obscure newspaper stops running her cartoon. She takes Richard on a road trip to the newspaper. Annie plots revenge on a critic who panned her performance.

Episode 22
Tue, Apr 22, 199722 mins
Caroline is having trouble getting the building superintendent to fix her shower so she hires an 'ombudsman' to intervene. Annie saves the life of a man in the audience of Cats and tries to use him to advance her career.

Episode 23
Tue, May 6, 1997
Caroline is to appear on The Tonight Show to publicise her new book. She accidentally takes some drugs before going on. Talk of who Richard's father is means Charlie goes looking for his. Del tries to give Richard some dating tips.

Episode 24
Tue, May 13, 199721 mins
Julia, Richard's old girlfriend, has returned with the news that she is getting married. He tries to impress her by asking Caroline to act as his wife. Then it becomes a game of oneupmanship between Julia and Richard.

Episode 25
Tue, May 13, 199721 mins
Sofia breaks off her engagement, stays over and forces Caroline and Richard to sleep in the same bed. However, Sofia has an ulterior motive. Caroline expresses her true feelings. Annie's role in a soap opera doesn't quite go as expected.