A hard-working New York lawyer striving for a promotion, Hugo Spencer (Ben Lewis) is using his Christmas break to return home to Milwaukee to visit family. Joining him is his lifelong best friend Madelyn "Maddie" McKay (Ellen Wong), with both receiving a warm welcome from Hugo's forever chipper mother Kate (Fran Drescher). As Hugo, Maddie, and Hugo's army brother Aiden (Chad Connell) get roped into helping Kate with their town's upcoming Christmas Eve festival, Hugo is suddenly reunited with Patrick Ryan (Blake Lee), a classmate from high school.
This summer, things aren't exactly going according to plan for college student and aspiring musician Cassie Temple (Natalie Sharp). With her Los Angeles music internship canceled, she'll have to settle for going home to her Washington hometown of Apple Springs for the break. It's after a chance encounter with Chloe Paine (Nicole LaPlaca) that Cassie lands herself a job babysitting for her six-year-old daughter Becca (Emma Oliver). At first, the gig couldn't be better, with Cassie quickly bonding with Becca and becoming friendly with Chloe and her husband Tom (Jon Cor).
With an Ivy League degree fresh under her belt, Jamie Kassman (Mia Topalian) is certain she's ready to take the business world by storm. But throughout her job search, Jamie is discouraged to find no employer is willing to hire someone fresh out of university with no experience. Just when things seem hopeless for Jamie, a big job opportunity falls into her lap: a nanny job for Walton Page (Coby Ryan McLaughlin), the billionaire businessman and philanthropist who Jamie has always idolized. Charmed by Walton's kindness to her and quickly bonding with his daughters Madison and Gwenny (AnaSofia Bianchi and Scarlett Fernandez), Jamie feels like she's found the perfect stepping stone for her career.
After an injury cost her a chance at a prestigious New York dance company, Elaine Davidson (Kristen Vaganos) is ecstatic when she learns she has the chance to finally have her audition now that she's recovered. During that time, Elaine has been babysitting Lilly and Mackenzie Cartwright (Hannah Aniela and Lyla Emerson Booker), the children of Silvia Cartwright (Dominique Swain). While her dance career has been on hold, Elaine has grown fond of taking care of the girls and is on friendly terms with both Silvia and Adrian (Simon Haycock), Silvia's psychiatrist husband and the children's stepfather.
While Abby Johnson (Jessica Morris) has been finding success in her rising photography career, her romantic life is a completely different story. Since breaking off her engagement to the possessive Richard Atkins (Jason-Shane Scott), he's been calling nonstop and harassing her in an attempt to get her back. Deciding she needs to get out of the city to clear her head, Abby takes up her editor Charlotte's (Vivica A. Fox) offer to rent out a past client's house in Kingston Bluff to work on a real estate photography project. Soon after getting settled into her temporary home, Abby slowly starts to unwind as she begins an unexpected romance with local bartender Logan Curtis (Justin Schwan).
Broadway stars Dee Dee Allen and Barry Glickman (Meryl Streep and James Corden) are in desperate need of image rehabilitation. After their latest show was canceled after one performance due to scathing reviews, Dee Dee and Barry's publicist Sheldon Saperstein (Kevin Chamberlin) inform them that the public sees them as narcissists. So along with fellow struggling theater actors Trent Oliver and Angie Dickinson (Andrew Rannells and Nicole Kidman), Dee Dee and Barry search for an activism project to get them the good publicity they need.
While she's spent much of her life traveling the world, food writer Leah Mitchell (Brittany Underwood) is finally ready to settle down after meeting the man of her dreams. Handsome and charming, Mark Pfeiffer (Greg Perrow) seems to be everything Leah could ask for. With her wedding day approaching, things should be like a fairytale for Leah. And they are...until Leah is suddenly attacked by an unknown woman, demanding she not marry Mark. After describing her assailant to her fiancé, Mark identifies the woman as Faith (Camila Banus), his ex-girlfriend who was institutionalized for psychiatric issues that cropped up during their relationship.
Trevor Wells: Hello Emily! Thank you for taking the time to talk with me. So to start from the beginning, what first got you interested in acting? I see your first IMDB-recorded role was in a show from my childhood: Ned's Declassified School Survival Guide.