After having a nervous breakdown, 25-year-old Josh Reeves gets booted from medical school. So he decides to go back home. So when he arrives, Josh discovers his mother Fran Reeves has gotten over her divorce and starts a new relationship with a hunky and young man named Riley. Josh also finds out that Riley is 6 months Junior to him. Also Josh discovers his room to be a gym, and Josh's walk in closet now belongs to Rileys buddy Duane. And Josh's bratty young teenage sister loves her new life style. At Fran's urging, Josh must learn to become a part of his new ""family.""
Fran invites Riley's parents over for dinner. Donna and Tom (Riley's mom & dad) are shocked when they meet Fran. Apparently, Riley has never mentioned that Fran is older, divorced, and with two children {oh yeah, and she's Jewish}. Tom (Rileys Dad) seems to except Fran and move on but Donna (Rileys Mom) just cannot seem to move passed Fran's age. After a small emergency, the two women realize that they both love Riley and will try to be friends.
When Fran is planning a family vacation her ex-husband Ted pays the family a visit. Ted comes beacuse he is trying to buy is family back by, trying to mend his relationship with Josh, buying Allison gifts and offering Riley a job he can't refuse. The whole family including Riley seems charmed by Ted, but the only one that is not charmed is Fran. Fran does not want her children to get hurt by their father again. Also Josh gets a job at a video store.
Fran's worries about impressing Riley's high school friends at Riley's high school reunion, but at the high school reunion Fran is being worshiped by Riley's friends' wives. Riley is also high-fived, but they soon think that Fran is Riley's ""sugar mama."" So during the a post-reunion gathering at their house, Riley is determined to prove to his friends that he is not a kept man. Also Fran is shocked to learn that the wives applaud her for having a boy toy.
Fran wants Riley to feel like part of the family, so she decides to start their own family album and is taken aback when Riley mentions adding pictures of their kids one day. Also Josh is comforted when Fran reassures him that being pregnant with him was the best thing that could have happened. So Riley gets his first taste of fatherhood when Allison starts to have boy problems.
Allison's new boyfriend Kurt makes alarm bells to go off for both Josh and Riley. So that causes Fran to re-think her trust in Allison's ability to make smart choices when it comes to dating.
Disapproving of Riley's plans for their first Valentine's Day together, Fran makes a few changes with out consulting Riley, making him feel that Fran controls the relationship. Also Fran does not know that Josh wants to break up with his girlfriend Lilly, so Fran advises her on how to win him over. And Fran's advice to Allison to pursue her secret admirer backfires when the secret admirer's identity is revealed.