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Valentine Farrow works for O.D. Dunstall in a New York publishing house. He is young and single and constantly chased by women. While in the Army, he was saved by "Rocky" Sin, a poker-playing con artist, who now serves as Farrow's valet. Sin lives in the basement of Farrow's townhouse with the handyman Grover Fipple. In the office, Libby is Farrow's secretary and Molly the receptionist.

After notorious English playgirl Daphne Kemp writes a tell-all book detailing her involvement in a juicy scandal, Valentine is tasked with obtaining the publishing rights to Kemp's book. Consequently, he must pull out all the stops with Kay Latimer in order to get close to Kemp.

With Carl's wife out of town, he, Valentine and the gang spend a weekend at a pretzel factory. The only problem is that his ex-girlfriend Stacy runs the factory.

Mrs. Dunstall returns from Europe ready to complete an important mission. She made a promise to Valentine's mother that she would help the perpetual playboy fund his way to the altar, and a prospect appears in the form of lovely research assistant Barbara Whitfield.

At the National Geographic Club, Libby, Rocky, and Molly disguise as club members in order to set a date for the panic-stricken club member.

Valentine's mother Muriel returns and is incensed to learn that her son is dating the daughter of Waldo Whitfield, a popular music critic. Clinging tightly to an old grudge against Whitfield, Muriel intends to throw cold water on Val's simmering romance.

The gang return to Chinatown once again, but Valentine falling in love with Audrey Westphall, the pretty schoolteacher from across the street. How would this end up?

It's Janet's birthday, and her husband Carl gives her a pet parrot who can imitate famous crooners such as Bing Crosby, Frank Sinatra, Perry Como, and many more. Janet loves the parrot but the canary has a few tricks up his sleeve.

Milquetoast nuclear physicist Dr. Delmore Link uses his mathematical prowess to devise a method in which the odds are in favor of a person's guaranteed ability to win poker games. To prove it, he's tricked into a game with Rocky and his buddies, then vanishes following a big loss.

Valentine gets a part-time job teaching history at an elementary school.

Valentine is faced with a problem of his own when he encounters three triplet sisters who try to seduce him into signing a contract.

Valentine gets a big surprise from an old Army buddy of his.

Valentine and Carl compete in a boxing tournament. Who will win?

Valentine and Rocky take a cab to go to the movies but Mr. Stevens, the cab driver takes the two into his apartment. There, Mr. Stevens and his wife have an argument that causes the landlord to kick them out of the house.

A date with Libby doesn't turn out the way Valentine expected when a book reviewer (Anne Francis) sits and talks with Libby the entire evening.

Valentine, Rocky and Libby try to save a married couple from getting a divorce. They even hire professional crooner Stevie Wonder to sing for them and to provide some marriage advice.

Valentine and Dunstall go on an all-expenses payed trip for two to Hawaii.

Valentine thinks he's been burning the candle at both ends for too long when he begins to discover Rocky in two places at the same time. Unknown to him, Rocky's belligerent lookalike cousin Putty Face Blue has been included in a book he is publishing, and is willing to go to any lengths to stop it.

Valentine finds his swinging bachelor pad suddenly overtaken by unexpected house guests. Hijinks ensue when his mother Muriel decides to pay him a visit, and Wampum, a Native American chief, arrives with the intent of taking Muriel as his Indian Princess.

Valentine and Jack are held hostage at a stationary store.

In honor of being employee of the month at the publishing firm, Valentine takes his workmates (Grover, Rocky, Libby, Cindy, Molly, Louie, and his boss Mr. Dunstall) to the movie theater to see Move Over Darling.

After Libby teases him for being an inveterate playboy, Valentine decides to prove his ability to make a mature commitment, which culminate in a spontaneous proposal of marriage. Wedding plans quickly overtake him as he struggles humorously against his newfound conformity.

Lovely research assistant Barbara Whitfield has Valentine in a lather. When she is in close proximity to him, he loses his cool, his quick witticisms, and even his shoes. The gang realizes that he's actually falling in love with the girl who isn't afraid to tell him "no".

Dawson Farrow, Valentine's swinging grand uncle, comes to visit. Claiming that he has been given only six more months to live, the lively old bachelor intends to enjoy a last grand fling and live the high life by liberating Val's credit accounts. He also has a final surprise in store for his nephew.

Valentine enlists the aid of his former college friend, professional footballer Jim Brown. It seems their aging English professor Charles Marks is lonely and hasn't slept well in fifty years. With Jim's help, Val hopes to reunite Mr. Marks with his long list love.