What If is a romantic comedy and adventure about a black and white photograph. Ailie Faulkner, a single, 39 year-old woman, married to her work, treasures a black and white photograph, and she's stored it in her closet for more than a decade. Like a wistful teenager staring adoringly at a poster above her bed, Ailie has spent years returning to this photo again and again, concocting fantasies and daydreams about the photo's handsome content. Prone to list making and overall levelheadedness, Ailie usually isn't one to believe in fate, but her curiosity (ahem, obsession ) with the photograph leads her to a life-changing decision and sends her on an adventure filled with humor, travel, bouts of nausea, unexpected discoveries, and reflections on cooking. Encouraged by her overbearing but obliging mother and an inquisitive grandmother, and guided by the insightful (albeit often contradictory) advice of her best friends, Ailie endeavors to learn about the photo, the person within its frame, and the possibilities of their future.