Some of the best classic rom-com movies are love letters to a specific city as much as they are love stories between two people. Love Lettering by Kate Clayborn fits right into that tradition. After calligrapher Meg correctly predicts the failure of uptight Reid's wedding, he's determined to find out how she knew before he did. She agrees to talk with him, but only if he'll help her find the inspiration she's lacking. As they bounce ideas about love, life, and work off each other, they spend their days exploring New York City, discovering all the secret spots and beautiful moments that just might lead them to love.