To take a break from the pressures of a major decision at work and the mess she’s made of her life, Nan decides to take a vacation.  On the way, she stops by her estranged father’s place in the country, hoping to say hi and go.  Instead, she discovers he’s selling the family home.  While Nan tries to pack up some childhood treasures, Dad takes Martin for a walk — but Martin, runs off into the woods, hoping to prove he’s wild and free like a wolf.  Instead, he discovers he’s not a wolf – he’s a dog who’s lost.

Nan’s long-anticipated national campaign is hours away from launching in Times Square on the Jumbotron, when an overwrought Nan discovers an algorithm  has been flipped, and instead of blocking penis photos from the photo feed it will choose them, which could torpedo the whole campaign. Meanwhile, Martin decides to reduce Nan’s stress by taking out his sworn enemy, Pepper, to unexpected results.

On his seventh birthday, all Martin wants is a nap, but his world is rocked when Jenn crashes at Nan’s house for a few days with her new puppy. Meanwhile, Jenn and Nan try to forget their respective romantic dramas by hitting the town, finding inspiration when they hear local celebrity Deejay Devine sing.

Nan visits New York with Jenn and Kevin for a big marketing meeting, leaving Jason to watch Martin at home, but Martin uses it as a chance to go on a trash-eating bender.

Nan meets Eric, an attractive dog owner who appears to be the older, more successful version of Jason, and enlists his help with Martin, secretly hoping to score a date. But when Martin spends time with Eric’s well-trained dog, it thrusts Martin into a crisis of self-confidence.

Frustrated by her boss Kevin’s interference in her ad campaign development, Nan brings Martin to work with her, hoping to keep dog-phobic Kevin at bay. However, she never anticipated that Martin would fall in love with Kevin.

When Nan installs an automatic dog door so she can take away Jason’s key but still keep him as Martin’s dog walker, Martin is convinced he can suddenly open doors with his mind, and the new-found power goes to his head. Meanwhile at work, Nan’s boss is unable to understand the new ad campaign Nan sold to the corporate bosses, and he spirals into confusion.

Nan struggles with a breakup and Martin's bad behavior, as he acts out in response to her newly busy work schedule.