In "Boomerang," a flailing millennial named Jake reconnects with his middle school crush, Emily, amid a series of comical mishaps in his adult life. Struggling with career setbacks and personal insecurities, he reaches out to rekindle their teenage spark. As they embark on awkward yet humorous outings, Jake tries to impress Emily, who has grown into a confident woman. Their journey reveals nostalgic moments, misadventures, and unexpected insights about themselves and each other. "Boomerang" is a lighthearted comedy that explores love, growth, and the balance between embracing the past and looking toward the future.