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At Amherst College in the late 1940s, freshmen roommates Jonathan and Sandy develop a friendly rivalry over their attempts at "scoring" on their dates with female coeds. The sexually aggressive Jonathan wants to be "smothered and mothered" by large breasts, while shy, romantic Sandy claims to value intelligence and sincerity. At a college party, Jonathan spots Smith College student Susan and, after summarily dismissing her breast size, encourages Sandy to approach her. Sandy's initial clumsy attempt leads to several dates with the intellectual and humorous Susan, which he then reports in detail to Jonathan. After Jonathan pushes him to "feel her up," Sandy persists in trying to touch Susan's breasts on a subsequent date, but Susan claims that she is not sexually attracted to him. Desperate, Sandy admits that she is the first girl that he has ever tried to touch in that way. Feeling sorry for Sandy, Susan allows him to touch her while she puts her hand on his penis. After Jonathan learns that Susan is more promiscuous than he had previously thought, he asks Susan to go out with him. While neither Jonathan nor Susan tells Sandy about the resulting romance, Sandy continues to tell Jonathan about his dates with Susan, claiming that he has fallen in love because she appreciates his sensitivity and intellect. On his next date with Susan, Jonathan, jealous that Susan likes Sandy more than him, tries to win her sympathy by fabricating a story about his humble childhood which led him to want to become a socially conscious lawyer. Several dates later, Jonathan's ploy pays off and Susan agrees to have sex, but does not enjoy the act. Jonathan describes his dates with Susan to Sandy, but calls her "Myrtle" to keep their betrayal a secret. When Sandy learns that Jonathan has lost his virginity with "Myrtle," he tries to have sex with Susan, who at first refuses but finally relents. Months later, Sandy confesses to Jonathan that he is jealous of the fact that Jonathan lost his virginity before him and continues to have more adventuresome sex than he does. One night, when the three friends go out together, Susan dances with both men, enjoying Jonathan's suave demeanor and easy footwork more than Sandy's awkward attempts at intimacy on the dance floor. Later, Jonathan, angry that Susan has told Sandy that she feels so close to him she can read his thoughts, demands that Susan choose between the two men. When they both agree to break the affair soon after, Susan suggests that they can still be friends, but Jonathan coolly remarks, "I hope not." Days later in Sandy and Jonathan's dormitory room, Susan and Sandy playfully argue like a married couple over packing for a camping trip while Jonathan sullenly watches. Over ten years later, the two friends meet and discuss their lives. Jonathan, who is now a taxman, is still the consummate playboy and complains that assertive women are gold-digging castrators and claims that he wants to settle down with someone "if their figure is good enough." Meanwhile Sandy, who has married Susan and started a family, is bored with their suburban life and jealous of Jonathan's sexual freedom. Soon after, Jonathan begins dating television model Bobbie, whose revealing clothing displays her voluptuous figure. After several weeks of dating and passionate lovemaking with Jonathan, Bobbie suggests they move in together, but Jonathan rejects the proposal, suggesting that it will ruin their sex. Soon after, Jonathan confesses to Sandy that he was experiencing moments of impotence but has been cured by his attraction to Bobbie's figure. After Bobbie moves in with him, Jonathan insists that she quit her job, promising to provide for her. Bobbie concedes in hopes of marrying Jonathan and having children, but he continues to adamantly resist to the idea. At home with nothing to do, Bobbie becomes increasingly depressed, rarely leaving her bed and barely capable of warming television dinners for Jonathan. Lacking in any tenderness, Jonathan constantly berates and humiliates Bobbie, causing her to weep in despair. After Jonathan rages at Bobbie for having a more "checkered" sexual past than him and orders her to do something useful like housework, a desperate and sobbing Bobbie states that she cannot stand her life. One night, when Sandy and his sophisticated mistress, Cindy, are at Jonathan's apartment to pick them up for a party, Jonathan tells Sandy that Bobbie is too passive, while Sandy claims Cindy dominates him in the bedroom. After Jonathan urges Sandy to swap partners for the night, Sandy agrees and goes to the bedroom to find Bobbie. Jonathan then dances with Cindy, who refuses his advances, confidently explaining that she will sleep with him but only on her terms. When Cindy leaves after ordering Jonathan to tell Sandy that he should not bother returning home if he sleeps with Bobbie, Jonathan opens the bedroom door to find Bobbie passed out from an overdose and Sandy calling an ambulance. Even as he witnesses Bobbie's despair, Jonathan can only yell at the unconscious woman that their relationship is "not going to work out." In the 1970s, twenty years since their college days, the now jaded middle-aged friends are still far from understanding love in a committed relationship. Wealthy Jonathan complains about his alimony payments to his now ex-wife Bobbie and their child, while Sandy, desperate to recapture his youth, dates demure eighteen-year-old Jennifer, dresses in hippie attire and espouses the "free love" of the new generation. When Sandy and Jennifer visit Jonathan, he presents a slide show of all his past lovers, including a picture of Susan which he attempts to ignore, referring to them all as "frigid ballbusters," and paints increasingly degrading verbal portraits of each woman, upsetting Sandy and Jennifer. Later, Jonathan confesses to Sandy that he has only glimpsed the illusive nature of love through brief sexual encounters, while Sandy laments that when he finally falls in love with a woman and makes a commitment, his sexual interest in them dies. With his impotence increasing, Jonathan seeks out prostitute Louise, who obliges Jonathan's obsessive request that she perform a verbal ritual worshipping men's "virile" and "domineering" behavior and castigating women as manipulative and castrating. When Louise veers slightly from the script, an enraged Jonathan, whose libido has immediately faltered, demands that she repeat the lines verbatim to ensure his satisfaction.