Riley begins to doubt his place in the family when the group, including ex-husband Ted, inadvertently walks in on their anniversary celebration at home. After arguing with Riley over the matter, a distraught Fran asks her cousin, Meryl, for words of wisdom and ends up mistaking her dog's medication for aspirin.
Fran takes Riley to his inaugural family function, a Bar Mitzvah, but when ex-husband Ted shows up with supermodel Rachel Hunter as his date, her plan to get some admiration by having Riley on her arm is ruined. Meanwhile, people think Allison is actually her gifted cousin, while Josh tries to hide the details of his job.
Fran goes to great lengths to give Allison a surprise Sweet 16 birthday, enlisting Gregory and Kyan Douglas to help set it up, despite Allison’s insistence that a party not be thrown. When Ted’s promise of Andy Vargas concert tickets for Allison goes unfulfilled, Fran turns to her friend Laurie to secretly get them in.
Fran laments her lack of acumen on the business end of interior decorating, prompting Riley to suggest she take a community college course to get familiar. She soon finds that she and Josh have signed up for the same class, but things get even worse for Josh when his mother gets the two thrown out of the class by cheating. Meanwhile, Allison abandons her yearbook duties to be with a new boyfriend, who is popular, just not in Allison’s house.
Fran tries to keep Allison from getting too heavy with her new boyfriend, Todd, when she catches her sneaking out the window to accompany him to a party. Meanwhile, Fran begins to think that Josh’s girlfriend, Taylor, spending the night at the house sent the wrong message to Allison.
When Riley's little sister comes to town for a visit, his protective big brother sense kicks in. After Fran asks Josh to take her out for a night of fun, however, the two come home married.
Fran tries to fix Meryl up with Riley’s pal, Danny, but is shocked to overhear Riley telling him about what is needed to date an older woman, an admission that makes her wonder about her own boyfriend’s seriousness. Meanwhile, Josh is saddled with his colleague’s little brother after an attempt to pawn off unwanted crush Becca on him goes awry.
Fran tries to get some free publicity for her business by getting a local journalist to write a piece on older women who date younger men. When Ted has a heart attack, however, Riley brings him into the home to stay for awhile, just as the writer comes to do the piece, and everything that could possibly make the household look chaotic inevitably seems to takes place.
When Fran's PMS becomes too unbearable for her, Allison tries to coax her onto birth control pills. Fran's parents, Bernie and Cookie, come for a visit and Cookie agrees with Allison, forcing Fran to demonstrate all over again that she can handle her sex life and parenting abilities. Her parents, however, don't immediately warm to Riley.
Fran and Riley attempt to gain some new clients for her interior design business by crashing a costume party. While at the party, Ryan awkwardly bumps into his former fiancé, Beth. Meanwhile, Allison is picked up by the cops for driving without a license, forcing Josh to cut short his date and prompting him to use her secret for leverage.
Riley lands Fran a decorating gig on his construction company's new development, but the two decide not to reveal their status as a couple to Riley's boss, Bryan. That plan goes awry when Bryan begins to get flirty with Fran and she goes along with it, but Bryan's daughter flirts with Riley, making Fran envious. Meanwhile, Josh and Allison end up in a game of jealousy when Josh starts tutoring Allison's best friend.
After Fran and Riley go out to eat and Fran is thought to be Riley's mother by their server, Fran dreams that someday the age difference between them will be very evident. She then decides to ask Riley to leave after worrying that their relationship will eventually consist of him taking care of her.
Fran and Ryan reunite at Meryl and Danny's wedding when Fran becomes Meryl's matron of honor and Riley becomes Danny's best man. Fran decides to bring Ted as her date, but when Ted starts to make a play for Riley's date, Riley decides to reach out to Fran.