Doctor, You've Got to Be Kidding! (1967)

Early twenty-something innocent Heather Halloran has always been pushed by her stage mother Louise to be a professional singer, although she doesn't really want that as a career--and has only modest singing talent. Instead she gets an office job and works as a secretary for Harlan W. Wycliff, who behaves more like a computer than a human and *knows* he's always right, especially about his secretaries falling for him because he's young, powerful, wealthy, and attractive. To prove Harlan wrong on another issue and thus knock down his superior attitude a notch or two, Heather takes Louise up on her offer for $5,000, which required Louise to re-mortgage her house, for professional help in putting together a musical act. Through her dealings with Harlan and the serious pursuit of that musical career, Heather embarks on trial relationships with three men who have doggedly pursued her: Dick Bender, a childhood friend and longtime neighbor who has been around the block a few times; Pat Murad, her arranger and singing coach, who is a bit of a lush; and Hank Judson, a shoe salesman and struggling actor who specializes in overly dramatic death scenes. In the process, Heather gets pregnant, and all three men, who each love her in his own way, want to marry her. But she comes to realize that she only wants the love of the one man who got her pregnant, and that's--the one who doesn't know he's the father.