In the charming Lake Harriet neighborhood where we first met Kristen, Ryan, and their dog Sam in Walking Sam, two people are struggling to put their lives back together with the help of a rambunctious dog named Bailey.

Lisa Evan's life has been in turmoil since her husband, Andrew, left her nine months earlier. With two-year-old Abby to care for and a new full-time job as a school nurse, she's just trying to keep her head above water both emotionally and financially. It didn't help that her ex-husband gifted a rambunctious puppy to Abby for her second birthday. But Abby instantly fell in love with Bailey, so Lisa didn't have the heart to say no. Even though Lisa's quiet neighborhood is a great place for kids and dogs, there's one neighbor who isn't thrilled about Bailey-the hermit across the street. And try as she might, Lisa can't keep the dog from digging his way out of the yard and running to the hermit's house. But after one particularly nasty clash with the hermit, Lisa discovers that maybe the man across the street isn't as terrible as she'd once thought.

Avery McKinnon moved to the quiet neighborhood to hide out after an extremely nasty divorce. In one year his entire world has fallen apart. His wife left him, he lost his house, and his novels are no longer selling as well as they used to, taking a bite out of his income. He's bitter and angry and the last thing he wants is to become chummy with all the annoyingly happy people in his neighborhood. When the puppy across the street keeps running over to his house and digging up his yard, Avery explodes. Can't that annoying woman across the street control a puppy? But when he finally sees Lisa for who she is, he realizes that maybe he's been angry long enough. Maybe it was time to let someone back into his life. And then her ex-husband comes back into the picture and ruins everything.