Once in awhile people get a second chance and for the Quimby family they are getting them in spades. After a faux date with Eli for her birthday, Jane finally gets the opportunity to go on a real date, while Ben gets a second chance of a lifetime when a minor league baseball scout wants him to try out for a coveted spot. With Dakota's proposal hanging in the air, Kate must decide on if she should give marriage a second chance or will she allow her commitment issues to scare her off again. But if Kate says yes, what does that mean for Jane and Ben? Will their second chance with their mother be over with her heading back to Colorado for marital bliss?.

With the school play's future in the lurch because of her, Jane decides to do something very unselfish - giving the play her well earned bonus check from Donovan Decker so the show can go on. But with the play back on, and getting some much needed help from the Donovan and Decker crew on the costumes, Jane feels like she may have given up more than just some money for this play.