Fifty-six year old Jerry Kingsley, the co-owner/co-operator of Lock Lee Fashions, a New York based garment manufacturer and wholesaler, has been widowed for two years. His older spinster sister, Evelyn Kingsley, moved in with him in his apartment following Jerry's wife's passing to take care of him, she who has always assumed the role as family caregiver. One of Jerry's married daughters, twenty-five year old Lillian Englander, believes Evelyn has a neurotic fixation on Jerry, Lillian unaware that her own fixation on her father is just as strong. Evelyn tries to arrange dates for Jerry, primarily with lonely widows, something he resists in wanting to find a woman on his own despite his own loneliness. Unlike his married business partner, fifty-nine year old Walter Lockman, who is always chasing after "tootsies" and "floozies", Jerry wants someone to love. After learning her story, Jerry thinks he's found the woman in Lock Lee's twenty-four year old receptionist, Betty Preisser. Betty, who never had much parental guidance, recently got divorced from her musician husband, George Preisser. There had always been a strong physical attraction between Betty and George, but nothing that she would now consider love. Betty is an extremely sad and confused woman, admits that she misses George, but doesn't want to get back together with him, she needing the antithesis of George as the person in her life at this point in time. Jerry and Betty enter into what ends up being a turbulent May-September relationship, their issues based on their own insecurities: Jerry, who realizes that his love for Betty is illogical due to the differences in their ages, admits he will always have pangs of jealousy in believing that she will be more physically attracted to men her own age; and Betty doesn't know if what she feels for Jerry is love or just a sense of being protected, something she never felt with George. Regardless, they decide to get married. That announcement opens up their relationship to the scrutiny of his family and friends, her family and friends, and their co-workers. The situation gets even more complicated when George reenters Betty's life. The questions then become if Jerry and Betty's relationship can withstand all these pressures, or if there is a factor or factors that will show them that their relationship makes sense at this point in their respective lives.