Caroline Duffy (Lea Thompson)

She was a cartoonist (author of the eponymous comic strip). She is from Peshtigo, Wisconsin and often tries to make everyone like her. She also has serious trouble not meddling in the lives of everyone around her. She was engaged to Del during the first season, but the marriage never took place and their friendship remained intact. She develops a contemporary attraction to Richard, however she does not develop it as early as him during the series. As her relationship with Richard seemed impossible she was temporarily dating a veterinarian Joe (during season 2), businessman Trevor (during season 3) and school time friend from Peshtigo, Randy (season 4). more >>>

Richard Karinsky (Malcolm Gets)

The colorist for the Caroline in the City comic strip. He was in love with Caroline. Caroline and Richard did end up having a relationship. There was no love lost between him and Del because of Del's relationship with Caroline and Del's lack of intelligence. Richard is highly sarcastic, especially to Annie. He is a struggling artist (painter) who usually lives in slummy parts of New York. He is regularly embarrassed about the nature of his job. A few times he had chances for his big break, but it always ended up as failure. Richard attended an unnamed art school, which he has a substantial student loan debt remaining for. more >>>

Annie Spadaro (Amy Pietz)

Caroline's across the hall neighbor and best friend. Annie was a dancer in the Broadway production of Cats. After meeting Shadoe Stevens in LA she quit her job in Cats and rushes to California to shoot pilot for series. Unfortunately she was fired from it and since she can't move back to Broadway she became unemployed until end of the series. She is somewhat promiscuous and wears unusual styles. Her mother Angie and brother Pete were recurring characters on the show. After Richard writes Caroline a love letter which he later regrets, Annie by accident manages to get her hands on it and makes several copies, which she used to blackmail him until her sister used it for a song. more >>>

Del Cassidy (Eric Lutes)

Caroline's sometimes boyfriend. They were engaged to be married during the first season, but broke it off in the season finale. Del worked at his father's greeting card company, but after he was fired he had to build his own business later in the series. Caroline becomes one of his only suppliers at this company, Eagle Greeting Cards. more >>>

Charlie (Andy Lauer)

He was a delivery boy in Del's father company and after Del was fired they became partners in new company Eagle Greeting Cards. He has a poor grasp on reality. In last season he has moved to Europe. more >>>

Remo (Tom La Grua)

Italian owner of restaurant Remo's Ristorante where other characters usually have dinner or spend time. Remo's Ristorante was mentioned in Richard's love letter to Caroline which later was used by Annie's sister to write song Meet me at Remo's. more >>>

Johnny (John Mariano)

Waiter in Remo's Ristorante. Usually takes part wherever Remo is. more >>>

Joe DeStefano (Mark Feuerstein)

Veterinarian who used to date Caroline and came close to moving in to her apartment for good. His character disappears from series after he confessess to Caroline that he slept with his ex-girlfriend. more >>>

Julia Mazzone Karinsky (Sofia Milos)

At the beginning of the series she was the love of Richard's life (as he calls it 'sincere amore' - the love that you don't have to question) and during Season 3 she becomes his wife. She's from Italy where they first met. She is the spoiled daughter of an Italian businessman who didn't approve of her relationship with Richard and tried to destroy him (first physically then economically). more >>>

Trevor (Robert Gant)

Caroline's boyfriend during the season 3. He owns a computer company and german shepherd dog. His character disappears in last episode of season 3 when Caroline rushes to Spain to meet Richard and Julia - Trevor realised that he will never win a place in Caroline heart over Richard. more >>>

Randy (Anthony Tyler Quinn)

Pediatrician, Caroline's schooltime friend (or boyfriend) from Peshtigo, Wisconsin. They meet in last season when Caroline's parents were selling their house. Since she grew up in this house she was trying to stop the sale and later was trying to buy it herself, but Randy already bought the house. When Caroline explained him how much this house means to her he agrees to sell it to her and rent it from her. When he arrives to New York for the pediatricians seminary they meet again and Caroline realizes that she may still have some feelings for Randy despite that she is in relationship with Richard. When Richard left to Italy to take care of his son Annie brought Randy to cheer Caroline up which ended up with their wedding in last episode, but since the ending was suspended and never finished there isn't any answer to question if Randy became Caroline's husband. more >>>

Also as guest stars:

Angie Spadaro (Candy Azzara)

Mother of Annie that constantly moves back to her daughter's flat which drives Annie crazy. During season 3 she got divorced.

Pete Spadaro (Adam Ferrara)

Brother of Annie that used to work in their father undertaking company. During the series he tries some other occupations influenced by Richard (electrician and artist painter).

Shelly (Lauren Graham)

Short time she was Richard's girlfriend. Richard was desperate to break up with her, but she always had reason not to.

Elevator Lady (Cathy Ladman)

Recurring character on the show - she was Caroline's neighbor from one of the upper floors. She often appears in key dialogues when someone enters the elevator. Also one of the episodes takes part in her flat.