In a world where dating apps promise effortless romance, a skeptical lawyer finds herself facing a most unusual legal challenge. Rachael Leigh Cook stars as Susan, a dedicated attorney who reluctantly takes on the case of a charming but persistent client, Nick, played by Damon Wayans Jr.. Nick has swiped through over a thousand dates on a popular dating site called Love Guaranteed, yet he has never found a lasting connection. Convinced the company is failing to deliver on its promises, he decides to sue them for breach of contract. As Susan and Nick work closely together to build their case, their professional partnership begins to blur the lines between logic and attraction. Directed by Mark Steven Johnson, this heartwarming romantic comedy balances sharp wit with genuine emotional depth, exploring the messy, unpredictable nature of modern love. With a delightful supporting cast including Heather Graham, the film offers a fresh take on the age-old question of whether true love can ever truly be guaranteed, leaving viewers rooting for a happily ever after that neither protagonist saw coming.