Allan Felix, a San Francisco film critic, watches the final scenes of Casablanca and finds himself inspired by the manliness and selflessness of the character of Rick Blaine, played by Humphrey Bogart. Soon, however, he reverts to his typical neuroses and insecurity, and recalls the recent departure of his wife Nancy, who left him to experience a more exciting life. Wondering how to be more self-confident, Allan imagines Bogart sitting in his room, advising him to treat women like dames. Later, Allan is visited by his best friends, overworked businessman Dick Christie and his wife Linda, a model. Although Dick tries to convince Allan that Nancy's exodus means Allan is free to play around, Allan complains that he has no luck with women. As Linda, another neurotic, and Allan commiserate and compare medications, Dick obsessively calls his office to report on his exact whereabouts. Although Dick and Linda love each other, she feels abandoned by his constant work schedule. The next day, Dick suggests a double date, and when Allan insists on a blonde with large breasts, Linda points out that girls who look that way often do not have great minds. As Allan imagines Nancy on the back of motorcycle complaining about him to her new boyfriend, Linda decides to invite her photographer's assistant, Sharon Lake, to dinner. Allan is immediately overwrought with excitement. At home, as Allan worries about the possible outcomes of the evening, Bogart recommends that he remain cool and calm. Allan imagines himself winning over Sharon with his manliness, but by the time of the date, he is verging on hysteria. Desperate to appear cool, Allan repulses Sharon with his bizarre utterances and uncontrollable clumsiness. Although he is convinced that she likes him, at the end of the evening she shuts her door in his face. Over repeated phone calls, he and Linda discuss his chances with women, and she suggests that he date her friend Jennifer. That date is even worse, however, as she calls herself a nymphomaniac but then refuses to allow him to kiss her. Allan and Linda go to the museum, where Linda admires his intensity, which is so unlike Dick. Allan asks out a beautiful girl, undeterred by her announcement that she plans to commit suicide that weekend. Days later, Allan, Dick and Linda take a vacation at the beach. Allan and Linda go to a nightclub, but the gorgeous woman on the dance floor rejects his advances. While Dick attends endless meetings, Linda and Allan enjoy each other's company. She urges Allan to be himself with women, and, knowing it is her favorite animal, he gives her a plastic skunk for her birthday, which she treasures. Dick later reveals to Allan that Linda feels neglected, but that he is too busy to dote on her. Dick sets up Allan with a woman from his office, Julie, and on their date Julie insists on entering a biker bar. There, two rough men harass them and Allan ineffectually attempts to protect his date. Meanwhile, Linda learns that he is on a date, and is surprised to find that she is jealous. When Allan returns, bedraggled and bruised, his comments about the date reduce her to tears of laughter. Back in the city, both Allan and Linda wander their respective homes feeling lonely. One night, Linda comes over, suffering an anxiety attack because Dick is away on a business trip. As they walk in the park, she suggests dinner and movie, and he immediately imagines them kissing. Realizing that he is in love with her but that, as his best friend's wife, she is off-limits, he is torn between lust and guilt. In the grocery store, Allan pictures Bogart encouraging him to come on to Linda while Nancy insists that Dick will beat him up, then hopefully imagines Dick asking him to look after Linda while Dick leaves to live with his new Eskimo lover. At home, he first prepares a romantic meal for Linda, and then, envisioning her screaming as he tries to kiss her, quickly snuffs out the candles. When Linda arrives she has taken Librium and is light-headed. Nervous, Allan tries to talk her in to leaving the apartment, but when she asks if he believes it is possible to love two people at once, he hears Bogart urging him to kiss her. He does not respond quickly enough, and when he tries again later, the kiss is interrupted by a phone call from Dick. Linda, who is becoming drunk, tells Allan she could only cheat on Dick if she were in love, and Bogart reappears to push Allan into making a move. As Allan apprehensively compliments Linda, he imagines Nancy entering and shooting Bogart. Confused, he lunges at Linda, who pulls away and rushes out. Allan is berating himself when she comes back in and kisses him. They make love, and the next morning discuss how to tell Dick. Allan brings Linda home then walks back to his apartment, feeling uncharacteristically cocky and gregarious. Buying Linda a music box, he runs into Nancy in a store and handles the meeting with aplomb. Later, he frets about how Dick will take the news, imagining him having three different responses: first understanding, then killing himself, then killing Allan. Dick is waiting outside Allan's apartment, and there confides that he is afraid Linda is having an affair. Seeing his friend's distress and repentance, Allan calls Linda to instruct her not to leave him, but she is already telling Dick that their marriage is over. When Dick leaves for the airport in response, Linda follows in a cab and Allan rushes after them. In his mind, his cab driver is Bogart, who demonstrates how to let a "dame" down easily, then declares he is proud of Allan for his selflessness. At the airport, the three get to the gate at the same time. Allan tells Linda they must call it off, but she has already reached the same conclusion, and thanks him for helping her realize she still loves Dick. Thrilled finally to have a chance to say the words, he recites the lines from the parting scene of Casablanca , in which Rick tells Ilsa that she will regret not following Victor onto his plane, ending with "Maybe not today, maybe not tomorrow, but soon and for the rest of your life." Allan then reassures Dick that although he tried to seduce Linda, she rebuffed him. As Dick and Linda walk off into the fog, Allan is joined by Bogart. Allan has finally realized that he can attract a woman by being himself, and so bids farewell to Bogart, who says admiringly, "Here's looking at you, kid."