Ann's career as an actress begins when she meets Donald Hollinger, a reporter for a magazine, while working as a candy clerk. Ann soon lands a part in a perfume commercial in which her character is kidnapped by two robbers. Donald thinks that Ann is in serious trouble, not knowing that it's for the chimerical, and steps in to "save her". But despite Donald's interference in her first real acting job, Ann and Donald begin to realize that they were meant to be together.
Ann finally leaves her mother and father's house to pursue her acting career in New York City. But when her mother comes for a visit and talks about moving in with her, Ann's dream of being independent may come crashing down around her.
Ann gets a big break when she get to audition for Jules Benedict, but complications arise when she also has to babysit for Judy. Can Ann pull of the audition and look after the baby?
Ann has to spend the day in court after she's involved in a freak accident involving a pedestrian and a sewing machine.
Ann brings Donald home to meet her parents, but things don't go as smoothly as Ann had planned when her parents make them stop for a roadside picnic.
After Ann is given expensive gifts from a rich man trying to win her heart, Donald becomes jealous and starts spending more than he can afford on Ann. Through it all, Ann comes to the realization that money isn't the most important part of a relationship.
Don learns the hard way that working with your girlfriend isn't the best idea after he hires Ann as his secretary.
Ann buys a box of junk with an old baseball in it at an antique auction. After the auction, a strange man follows Ann around because he wants to get the baseball.
After being in the wrong place at the wrong time, Ann finds herself in jail. At a restaurant, Ann tries to help a waitress as she waits on two rival gangs, and when the police raids the restaurant, Ann is taken into custody.
Sandy, a friend of Ann's, landed a role in a big-name Broadway production. When Sandy gets sick and cannot do her part in the show, Ann fills in for. However, everyone thinks that Ann stole the part from Sandy, but Ann tries her best to enjoy her chance to be on stage.
Ann is convinced that she'll need a different name to make it in show business, so she goes about trying to come up with a better name.
Ann meets Don's parents for the first time, but Don's mother takes an instant disliking to her because of the roll Ann has on a soap opera.
Ann thinks that Don will fall in love with a famous actress after he does some interviews for an article that he's writing.
Donald and Ann meet an old organ player who used to play for old silent movies. After Donald does an article on him, the man disappears and Ann and Donald soon learn that he's a known, and very wanted, criminal.
Ann is given gifts by one of her fellow acting class students. Donald and Ann start to think that the expensive gifts were stolen by Hobart, but they soon learn that he's a very wealthy man.
With Christmas spirit in the air, Ann tells Donald a story about a time when she was a teacher's aide. During that time, Ann stayed behind to care for a boy during the Christmas vacation while his parents were away filming a movie and couldn't get back in time for the holidays.
While going through old things, Ann comes across souvenirs that remind her of her former boyfriend, Freddy. As Ann continues to think of him, she discovers that Freddy still has feelings for her.
Ann gets a job as a shoe saleswoman. But these aren't normal shoes: they fall apart soon after walking in them.
To help Donald out, Ann hires him a maid. Ann soon regrets her decision when she becomes jealous of the maid.
Donald lends Ann a manuscript of a novel that he is writing, but while she's reading it, she looses it. When Donald asks her what she thinks of it, Ann has to stall because she's afraid to admit that she lost the novel.
Ann and Donald are invited to a wedding by Jerry and Margie in Connecticut, but while there, they get snowed in. Since their inn only has two rooms available, the boys stay in one room while the girls stay in another. However, when Jerry and Margie decide to stay in the same room, Ann and Donald are forced to share a room, much to the disgust of Ann's parents.
Ann is lead to believe that she's getting a surprise birthday party when she gets invited out to dinner by her father.
Lou starts to think that Ann and Donald should get married, but Ann and Donald think otherwise.
Ann helps Donald to get an interview with a famous opera singer for a story he's working on. But the article might be threatened when Donald has a hard time controlling his romantic urges.
Ann invites her parents and her Aunt Harriet to dinner in order to prove to them that living in the city isn't all that bad. However, Ann has a hard time proving it when a strange man outside Ann's window tries to woe her.
Ann reads an article about how a producer is looking for an unknown actress for a play, so she has Donald put in a good word for her. Donald talks to the producer, but learns that he already found a star for the play. He tries to break the news to Ann, but she just won't listen.
Ann is visited by her cheap cousin and his new bride after their wedding because her cousin doesn't want to pay for a honeymoon. When he refuses to leave, Ann is able to get them a bridal suite, buying her time to plot a way to get them to leave.
Ann is the center of mishap and comedy when she gets her toe stuck in a bowling ball.
In order to do well in an audition, Ann enlists the help of Donald to write funny material. Though Donald is a skilled writer, his jokes arn't funny.
Donald is assigned to do a story on "The Mating Game", so he has Ann be a contestant. However, Ann doesn't know that Donald is one of the contestants and choses another man instead. While on her date with the bachelor she picks, Donald tags along to get the story.
Ann is elated but nervous when she learns that she'll be on stage with the famous Ethel Merman who chose Ann for a walk-on role in "Gypsy".
In order to get a part in a commerical for a brand of soda, Ann must learn to rollerskate.
Donald, having finally finished his novel, begins to send it out to publishers, but starts to get discouraged when after the twelfth rejection slip arrives in his mailbox. Ann's father tries to help, since he has connections, but after reading it, Lou refuses to send it to the publisher he knows.
While researching for an article on computer dating, Donald does a Compudate and ends up paired up with an attractive model, making Ann jealous. So to get back at Donald, Ann does her own Compudate and ends up with a man a lot like Donald.
While Ann's apartment is being painted, she is forced to borrow Donald's apartment for her new telemarketing job since Donald's out of town. But complications arise when Donald's friend Harry comes by to stay in the apartment without Ann knowing.
Ann is tricked by a con-man into shoplifting. But will Ann pay the price for someone else's plot?