The movie Playing Cupid follows the story of Claire, a recently divorced middle-school teacher who is struggling to move on from her failed marriage. One day, as part of a school project, Claire assigns her class to start a business with a partner. One of her students, Maddy, decides to start a matchmaking business and chooses her recently divorced father, Jack, as her partner.
As Maddy and Jack start matchmaking people around the school, Maddy decides to secretly set up Claire with her dad, hoping they will hit it off. Claire is hesitant at first, but Jack proves to be a kind and caring man who quickly wins over her heart. As they start dating, Claire and Jack navigate the challenges of being single parents while also trying to find time for their growing relationship.
However, their budding romance is put to the test when Jack's ex-wife returns to town and tries to win him back. Claire starts to feel insecure and wonders if she's ready to take a chance on love again. With the help of her supportive friends and Maddy, who is determined to see her dad and Claire end up together, Claire must decide if she's willing to take a risk and follow her heart.
Playing Cupid is a heartwarming romantic comedy that explores the ups and downs of finding love again after a failed marriage. It's a feel-good movie that celebrates the joy of second chances and the power of love.