Last of the Red Hot Lovers

Last of the Red Hot Lovers is a comedy by Neil Simon. It premiered on Broadway in 1969. Barney Cashman, a middle-aged, married nebbish wants to join the sexual revolution before it is too late. A gentle soul with no experience in adultery, he fails in each of three seductions: Elaine Navazio, a sexpot who likes cigarettes, whiskey, and other women's husbands; Bobbi Michele, an actress friend who he discovers is madder than a hatter; and Jeannette Fisher, his wife's best friend, a staunch moralist. (Source: Wikipedia)

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https://en.wikipedia.org/wiki/Last_of_the_Red_Hot_Lovers