Caroline in the City

Caroline panics when she realizes that several hours have passed since she poured her heart out to Richard on his answering machine and she hasn't heard a response from him. Richard arrives with some surprising news.

Caroline realizes that she has unresolved feelings toward Richard, but she doesn’t let it get in the way of helping Richard navigate through troubled waters with Julia.

When Caroline discovers that she’s been receiving free cable, her honesty with the cable company gets her into deep trouble with her not-so-truthful neighbors. Julia throws Richard a surprise birthday party, but Richard is not in the mood to celebrate when he discovers that his ex-therapist wants to date Annie.

Caroline feigns having read a writer’s novel to impress him, but their first date is a disaster as Caroline’s charade quickly crumbles.

Caroline decides not to endorse a local councilman, who says is inspired by her comic strip. Annie tries to convince her visiting young cousin Jennifer that she should stay at school.

Caroline goes out of her way to help Richard find a misplaced and beautiful family wedding ring for Julia. Also, Del and Charlie come up with a creative plan to make Caroline in the City the star attraction on the Christmas tree at Rockefeller Center.

Caroline is excited to go on a blind date that Julia has set for her and handsome businessman Trevor, while Richard ties hard to spoil that evening. Annie enlists Del to help her seek revenge on her former classmates at her high school reunion.

When Annie is visited by her old singing teacher, Caroline helps Annie pretend to still have her Cats role. Richard joins Charlie in a quick money-making scheme of drug testing.

Caroline’s former assistant asks Caroline for a maternal donation. Richard struggles to live up to Jeannie’s legacy as Caroline’s most dedicated and fun-filled assistant.

Caroline tries to convince insecure Del that he has the potential to be a great parent after Del is shocked to discover that he is the father of a 10-year-old girl.

Richard relives his tortured youth when he confronts his former piano teacher, Marvin Hamlisch, and accuses the Grammy Award-winning composer of plagiarism.

Discreetly planning to ease Caroline’s homesick holiday blues, Richard goes to great lengths to get a gift for Caroline that inspires suspicion in Julia and sleuthing from Caroline and Annie.

Caroline winds up spending Christmas with Del's family when a snowstorm grounds her parents in Wisconsin. Charlie and his father, Doc share their first Christmas together.

When Caroline is tapped as a celebrity guest star for a quiz show, her jitters prompt Richard to help her study, much to Julia’s anger.

Informed by Annie of Caroline’s unspoken love for him, Richard confronts Caroline, who tells him that it’s a thing of the past. To prove she’s over him, Caroline throws a lavish party for Richard, Julia and Trevor.

When Julia tells Caroline that it’s not easy being on the outside of her close working relationship with Richard, Caroline quickly, and mysteriously, learns what it’s like to walk a mile in Julia’s shoes.

As Caroline struggles with commitment issues over Trevor, Richard inadvertently causes a rift between Caroline and her boyfriend. Annie is delighted to learn that her mother, Angie is finally going to move out of Annie’s apartment. Del and Charlie plot a Groundhog Day publicity stunt for Caroline’s card line.

When Caroline is insulted by a cabbie, she takes her case to higher powers at the travel commission. Meanwhile, Richard frustrated by a painter’s block, becomes obsessed with computers when he joins a cybercafe.

Richard is nervous when Julia’s father, Carlo Mazzonetakes him on a bonding trip in a small plane, but Caroline helps him through the rough moments.

Julia convinces Richard that they should see a counselor, who insists he should quit his job. Caroline must hire a new cartoon colorist, who turns out to be... the counselor, who convinced Richard to quit.

Taking advantage that Caroline’s new assistant used to be marriage counselor Caroline and Trevor try to come to terms over their own troubled relationship, while Del and Charlie have their own unresolved issues.

Caroline is reluctantly pulled into the national spotlight with Jo Anne Worley when Del and Charlie get a deli owner to re-name a Worley sandwich after Caroline in the City.

When Caroline’s mother visits Caroline for a mother-daughter People magazine shoot, tensions rise over unexpressed feelings. Annie tries to convince Caroline that the only way to grow closer to her mother is to be honest.

Caroline is drawn into Angie Spadaro’s New Jersey-based world when she tries to help her deal with the wedding of her ex-husband. Meanwhile, Richard is called to jury duty and must go through trial and error selection for a specific case with the help of a fellow jury expert. Del and Charlie feign a gay relationship with each other in order to receive better insurance benefits.

Richard and Julia agreeing that she’ll go to Spain to party with her friends in the summer, while Richard stays in New York to begin painting again. But when Caroline inadvertently tells Richard that she thinks Julia is having an affair with a Spanish bullfighter Richard takes off for Spain to confront Julia.

Realizing that Julia did not sleep with the bullfighter, Caroline and Annie fly to Spain to right their wrong, and they run into Richard during the running of the bulls.