Serendipitous Annie

New York City local morning show host CHARLIE KLINE (34) cherishes his high-profile job and sweet son, ETHAN (4). A hunky widower, Charlie relies on a nanny, with his straight-talking mother, MAGGIE (59), and pragmatic neighbor, MRS. ROSENBERG (60s), pitching in. A doting father, Charlie gets an important call as he and Ethan play in Central Park. He’s deep in conversation when ANASTASIA BLOOM (46), a cheerful and fun children’s author, sees a bully shove Ethan and hurries to help him. Upon noticing the kerfuffle, Charlie rushes to his son—who clings to Anastasia. Savoring the motherly affection, Ethan won’t budge when stunned Charlie tries coaxing him away. When Anastasia, a widow from Iowa City, asks for directions to a café, Ethan asks to eat with his new ally. Equally charmed, Charlie’s happy to indulge him. During lunch, the nanny texts Charlie that she’s quitting—immediately! He panics since both his mom and Mrs. Rosenberg are out of state. Ethan suggests Anastasia stay with him, flustering Charlie. Midwest-nice Anastasia, who’s a tad naïve, offers to fill in for a week since her daughter KATELYN (16), an edgy artist, is an exchange student in Paris. Desperate (and captivated), Charlie takes her up on it. After a few days of Anastasia’s whimsy and contagious joy, Ethan’s thriving—and Charlie can’t imagine anyone else caring for him. He convinces her to stay for the year Katelyn’s away. Anastasia’s saucy bestie, PIPER (40s), insists it’s time for her to date again and urges her to pursue hot-shot Charlie. Focused on Ethan and cognizant of their 12-year age gap and her daughter’s intention to return to Iowa City for her senior year, Anastasia pooh-poohs the idea. When Charlie can’t stop singing her praises, his insightful network buddy, GORDON (50s), suggests he make a move. In denial about his budding feelings, Charlie also fears scaring her away since Ethan adores her. To Charlie’s chagrin, Anastasia begins dating suave PHILLIP (50s). He shifts his focus to NATALIA (32), a sultry correspondent. Charlie’s heart wins out after he and Anastasia both find themselves single the same night. He shoots his shot, stunning Anastasia— who’s never guessed he’s been pining for her all along. He’s also been pining for the coveted evening news assignment opening soon. But when private Charlie introduces her as “Annie” to bigwigs at a network gala then hesitates to rebut their snide jokes about her due to his pending promotion, Anastasia realizes she’ll never fit into his glitzy, pretentious world. She returns to Iowa, devastating Ethan—who regresses and burns through two nannies. After he dates several plastics, Maggie prods spiraling Charlie to reconcile with Anastasia, whom he knows (via scheming Piper’s social media posts) has moved on with classy JUDE (40s). After texts, calls and bouquets begin to sway Anastasia, Piper helps Charlie coordinate a surprise visit, where he informs Anastasia that he declined the promotion due to family-unfriendly hours. He implores her to give him another chance and return to NYC. After consulting with Katelyn, who notes she seemed much happier with Charlie and Ethan, Anastasia agrees. Charlie surprises her and flies Katelyn to NYC for Christmas. After cutting a deal with Katelyn, Charlie proposes on Christmas Day, culminating in a joyful final scene wedding.