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 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 hell lose his virginity to her. He goes through the process methodically, considering what she wants, but theres 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 others 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. Jonathans sexual trajectory, directed through these experiences, ends up in a manner he probably did not foresee.
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.
 
		 Jack Nicholson 
 Jonathan
 
		 Candice Bergen 
 Susan
 
		 Art Garfunkel 
 Sandy
 
		 Ann-Margret 
 Bobbie
 
		 Rita Moreno 
 Louise
 
		 Cynthia O'Neal 
 Cindy
 
		 Carol Kane 
 Jennifer
 
		 Ray Cass 
 Man
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