Kate Fox followed the rules all her life... until she got pregnant in college and dropped out just shy of graduation. After the birth of her daughter, Maddie, Kate put her twenties on hold. Now working as a bar manager to make ends meet and maximize her time with five-year-old Maddie, she's uber-prepared for every possible catastrophe - except for the arrival of her older brother, Ben Fox. Ben likes trouble a lot more than his sister does. His infectious energy makes you want to follow him into any number of bad ideas. He'll totally screw up your life, but somehow, you'll feel good about it. Where Kate is all about planning and preparing, Ben is big on spontaneity and out-of-the-box ideas.
But don't let the Velcro wallet fool you - he'll probably be a millionaire someday. When Ben comes to crash on Kate's couch for a few days, he finds a sad state of affairs. Kate's surviving, but not living. Ben realizes that for the first time in their lives, Kate needs his help and he's determined to bring some much-needed chaos into her overly stable world. He starts by offering to help look after Maddie so Kate can get back to experiencing her mid-twenties and making mistakes, since the one real "mistake" she's made turned out to be the best thing that ever happened to her. Always there to help with Ben's crazy schemes is his partner-in-crime, Tommy, who worships Ben like a hero and nurses a serious crush on Kate. Kate's British best friend, BJ, is a cocktail waitress at the bar that Kate manages and an all-around hot mess who would do anything for Kate, even if her advice is often questionable and occasionally illegal.