Pillow Talk (1959)

Plot: In New York City, Brad Allen is a Lothario, a songwriter who casually strings along several women at one time, they who willingly follow. Jan Morrow is an interior designer, who is saving herself for Mr. Right. Although they have never met face to face, they know each other since they share a telephone party line. Jan is not only irked by Brad always seemingly being on the telephone when she needs it, but is also disgusted by his telephone conversations, which generally include serenading these unsuspecting women with the same original song, only changing the name to fit the woman in question. Brad, in turn, doesn't like what he sees as Jan meddling in his affairs, which he argues is because she is repressed sexually. There is a mutual attraction between the two upon a chance face to face meeting. While she does not know who he is, he knows who she is, and thus passes himself off as a chivalrous Texan named Rex Stetson instead of his true self. He is perpetuating this ruse in part to get to know her better, but also so that he as Brad Allen can taunt her over the telephone about her affairs about which he would have inside knowledge without her knowing it. It works as Jan falls for Rex. The situation is even more complicated in the form of millionaire Jonathan Forbes, one of Jan's clients who is in love with her, but she not with him. Jonathan also happens to be Brad's oldest and dearest friend, who has commissioned Brad to write songs for a Broadway show. The person who may be able to get them all out of this complicated situation is Jan's drunkard of a housekeeper, Alma, who is Brad's most devoted telephone eavesdropper, and who truly does live vicariously through Brad's telephone calls.