The story follows Leah, played by Bailee Madison, a young woman who is completely burned out on dating and ready to give up on love altogether. Just when she decides to quit, her grandmother, played by Annie Potts, steps in with an outrageous challenge: go on 40 dates in 40 nights—and if she completes it, her rent is paid for an entire year. What follows is a whirlwind of awkward dinners, mismatched personalities, and surprising emotional connections.
As Leah moves through a rapid-fire series of dates, she begins to realize that the real challenge isn’t finding “the one,” but understanding herself. The trailer teases both comedic chaos and heartfelt moments as she stumbles through everything from cringe-worthy conversations to unexpected sparks that make her question her approach to love.
The film also features Joel Courtney as a potential romantic interest, alongside Jai Rodriguez, Jack Schumacher, Luxy Banner, Eric Nelsen, and Annie Potts in a standout supporting role as the bold and unconventional grandmother who sets the entire challenge in motion. The ensemble cast adds variety to Leah’s dating journey, with each encounter offering a different perspective on modern romance.
Directed by British indie filmmaker Andy Delaney, known for Love Is Blind and Crossroads, the film aims to blend quirky humor with emotional depth. The screenplay is written by Sarah “Howie” Howard, bringing a contemporary voice to the story that reflects today’s fast-moving dating culture and emotional burnout.
Set to release on June 16, 2026, 40 Dates and 40 Nights promises a fun, relatable, and heartfelt rom-com experience that explores love in the age of speed dating, apps, and emotional exhaustion. The trailer suggests a film that is equal parts chaotic, charming, and surprisingly sincere.
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