Recently divorced Valerie and her 16-year-old daughter Laura move in with Valerie's brother Alex. An eternal bachelor and master of casual dating, Alex sets Valerie up on a date via his popular dating site. Brother and sister go on separate dates at the same restaurant that night.

Alex spends the day with Valerie's one night stand Leon, and winds up having a crazy night. Valerie goes out with a group of 20-something girls who coach her on dating young men. Laura gets in trouble at a high school house party.

Valerie decides to move out of Alex's house but is blindsided by the financial repercussions of divorce. Alex adopts a dog. Laura fantasizes about her photography teacher Michael.

Valerie breaks Alex's rules of casual sex. Alex is interviewed about his dating site. Laura makes a move on her teacher Michael.

Valerie and Alex's mother shows up unannounced. Valerie gets good advice from an unlikely source. Laura and Michael share a moment after she sees her father out with his new girlfriend.

Alex's secret profile gets its first real match. Laura bonds with Michael after her sex tape goes viral at school. Valerie gets closure with her ex-husband.

Alex and Emmy have a foursome. Laura discovers Valerie as been seeing Michael and moves out.

Laura, now living at her father's house, invites her dad's girlfriend and her estranged grandparents to Thanksgiving dinner. The night ends with hurt feelings, slammed doors and broken dishes.

Tensions run high at Dawn and Charles' rehearsal dinner. Laura is humiliated after showing up at Michael's art exhibition. Alex finds Valerie and Emmy in bed together after an ecstasy trip.

Valerie and Emmy search for Alex at home but find Laura instead. Alex looks to Leon for support. Valerie and Alex make up at Dawn and Charles's wedding.