Jack Sullivan, an older man, is dating Sarah, a younger woman. The story begins with Jack meeting Sarah’s mother, Claire, who is initially skeptical about their relationship due to the age difference and Jack’s recent divorce. Despite Claire’s reservations, Jack and Sarah seem to have a romantic connection.

Jack's attempt to fit in with Claire and her family is met with various awkward and humorous situations. He faces disapproval and discomfort, particularly when Claire’s old friends and visitors come into play. Despite his efforts, Jack's relationship with Sarah faces challenges due to their differing lifestyles and generational gaps.

As Jack's divorce progresses, Sarah decides to end their relationship. She admits that while Jack is a great person, they are too different and that she has developed feelings for someone else. Jack accepts the breakup with understanding, reflecting on the complexities of their relationship and the impact of their differences. The story highlights the difficulties of navigating a romance with a significant age gap and the unpredictable nature of love.