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.