Anchor plot: Gus Kubicek (played by Guttenberg) is a depressed and overweight cartoonist who recently won a battle against Hodgkin's disease. His caring sister Lizzie Potts (Long), a nosy romance novelist, responds to his sadness by trying to set him up with a suitable woman. Yet to do so she must make him seem more dynamic and attractive. When Gus falls in love with Emily Pear (Gertz), he adopts the persona of Lobo Marunga, a leather-clad biker from New Zealand.
Emily ends up falling for Lobo but Gus tries to tell Emily the truth as he ends up in bed with her. The next day Lobo tells Emily that he's Gus and she gets furious with him and tells him to get out. Gus, hurt, supposedly goes away to New York when in fact he is going to a friend's wedding. The movie ends with Emily tracking down Gus at the airport and they share a kiss as Lizzie watches through binoculars.

Plot A: In the resort of Lake Waxapahachie in New Hampshire, the swanky Wentworth Plaza is where the rich all congregate, and where the tips flow like wine.  Handsome Dick Curtis (Dick Powell) is working his way through medical school as a desk clerk, and when rich, penny-pinching Mrs. Prentiss (Alice Brady) offers to pay him to escort her daughter Ann (Gloria Stuart) for the summer, Dick can't say no – even his fiancée, Arline Davis (Dorothy Dare) thinks he should do it. Mrs. Prentiss wants Ann to marry eccentric middle-aged millionaire T. Mosley Thorpe (Hugh Herbert), who is a world-renowned expert on snuffboxes, but Ann has other ideas. Meanwhile, her brother, Humbolt (Frank McHugh) has a weakness for a pretty face: he has been married and bought out of trouble by his mother several times.
Every summer, Mrs. Prentiss produces a charity show for the "Milk Fund", and this year she hires the flamboyant and conniving Russian dance director Nicolai Nicoleff (Adolphe Menjou) to direct the show. The parsimonious Mrs. Prentiss wants to spend the least amount possible, but Nicoleff and his set designer Schultz (Joseph Cawthorn) want to be as extravagant as they can, so they can rake off more money for themselves, and for the hotel manager (Grant Mitchell) and the hotel stenographer Betty Hawes (Glenda Farrell), who's blackmailing the hapless snuffbox fancier Thorpe.
Of course, Dick and Ann fall in love, Humbolt marries Arline, and the show ends up costing Mrs. Prentiss an arm and a leg, but in the end she realizes that having a doctor in the family will save money in the long run.

Plot B: Leon Phelps (also known as the "Ladies Man") was a Saturday Night Live character played by Tim Meadows during the 1990s.  The sketch was that of a broadcast program in which Phelps, a young, suave black man, would give dubious romantic advice and lovemaking tips.  The Ladies Man openly proclaimed that he would court any woman at all including skanks, providing the woman weighs no more than 250 pounds.  A night of romance would generally revolve around a bottle of Courvoisier.
After finally going too far during a broadcast, Leon is fired, but he receives a note from one of his former flames who wants him to come back to her—and is willing to support him in high style. This sounds just fine with Leon, except that the woman didn't sign her name, and now Leon has to backtrack through his numerous conquests of the past and figure out who wants him to work his love magic. Meanwhile, a secret group called the Victims of the Smiling Ass (V.S.A. for short), consisting of the angry husbands and boyfriends whose women have cheated with Leon, have discovered Leon as their target and are now hot on his trail, eager to get revenge.