Chronicling the romantic relationships of two men who meet and become friends in college.
The concurrent sexual lives of best friends Jonathan and Sandy are presented, lives that are affected by the sexual mores of the time and their own temperaments, especially in relation to the women in their lives. Their story begins in the late 1940s when they are roommates attending Amherst College together. Both virgins, they discuss the type of woman they would each like to end up with. The more-sensitive Sandy meets Susan at a mixer and believes he'll lose his virginity to her. He goes through the process methodically, considering what she wants, but there's little true passion or romance. The more sexually-aggressive Jonathan, loses his own virginity to "Myrtle," a steady but hidden girlfriend. Based on what each knows of the other's relationship, both men strive for a little more of what the other has. These relationships also set the tone for all the relationships they will have in the future. Through their lives, they always seem not totally satisfied with each relationship, still pining for what the other has. This view might change as they and their friendship hits middle age, when Sandy is with a domineering woman named Cindy, while Jonathan is with model/actress Bobbie, whose life goes spiraling downward because of her relationship to Jonathan and despite her beauty which on the surface offered so much opportunity for her. Jonathan's sexual trajectory, directed through these experiences, ends up in a manner he probably did not foresee.—Huggo
Jonathan and Sandy are roommates in the university. Each has a different behavior and experience with women. Jonathan is cynical, malicious, and selfish. He does not respect anybody (even his best friend is not respected) and just want to have sex; women are objects for him. Sandy is almost the opposite of Jonathan and has a different approach with women: he is shy, sensitive and respectful; he does not have much experience with women. Sandy dates Susan but Jonathan passes on her at the beginning of a love triangle. A few years later, Sandy and Susan are married and Jonathan and Sandy are successful professionally and boring with their mates. Then, Jonathan has a relationship with the sexy Bobbie. As years go by, the two friends have affairs with different women but no steady relationships.—Claudio Carvalho, Rio de Janeiro, Brazil
The film traces the sexual and emotional confusion of two men from their Amherst College days in the fifties through the Kennedy sixties, up to the Vietnam era. Jonathan, a successful tax attorney and Sandy, a physician, personify two extremes of self-delusion and self-aggrandizement: Jonathan makes the mistake of thinking sex is love, and embarks on a lifetime of sexual conquest; Sandy dedicates himself to the pursuit of an idealized woman and the dreamy spiritual completeness to be found therein. In Bobbie Jonathan finds a partner whose masochism compliments his selfishness and emotional ambivalence. Jonathan does not want her to hold a job, but neither does he like the fact that she spends all day in bed sleeping, or watching TV. Sandy falls in love with his first college romance, Susan; they marry and have children. But Sandy is haunted by the fear that he was too hasty, even though he and Susan lead a happy domestic life and strive to reinvigorate their sex life by making love "in all seven rooms" of their apartment. With Jonathan's help, he enters into an affair with Cindy, a tough professional woman who turns Sandy off because she is too overbearing.—alfiehitchie
At Amherst College in the late 1940s, freshmen roommates Jonathan Bates (Jack Nicholson) and Sanford 'Sandy' Cohn (Art Garfunkle) develop a friendly rivalry over their attempts at "scoring" on their dates with female students. The sexually aggressive Jonathan wants to be "smothered and mothered" by large breasts, while shy, romantic Sandy claims to value intelligence and sincerity.
The film opens at a college party where Jonathan spots Smith College student Susan (Candice Bergman) 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 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 during the winter, 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.
The film then jumps forward around 10 years later. The two friends meet at an ice skating rink in New York's Central Park and discuss their lives. Jonathan, who is now a taxman, is still the consummate, slightly misogynist 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".
Sandy, who has married Susan and started a family, is bored with their suburban life and jealous of Jonathan's sexual freedom. Sandy eventually tells Susan that he wants a divorce, and she throws him out of their house.
Meanwhile, Jonathan begins dating model Bobbie (Ann-Margaret), 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 lives. 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 the idea.
At home with nothing to do, Bobbie becomes increasingly depressed, rarely leaving her bed and barely capable of serving 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 new sophisticated girlfriend, Cindy (Cynthia O'Neal), 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 present day 1970, more then twenty years since their college days, the now jaded middle-aged friends are still far from understanding love in a committed relationship. Wealthy Jonathan, now living in a large apartment penthouse, complains about his alimony payments to his now ex-wife Bobbie and their child, while Sandy, desperate to recapture his youth, dates demure 18-year-old Jennifer (Carol Kane), 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 lovers, including a picture of Susan which he attempts to ignore, referring to them all as "frigid ball-busters", 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.
In the final scene, with his impotence increasing, Jonathan visits aging prostitute Louise (Rita Moreno), who obliges Jonathan's obsessive request that she perform a verbal ritual worshiping 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.
