His Christmas plans include starting a foundation to help kids get out of his old neighborhood. However, quarterback Will Kent throws a wrench in Evan's plans with a bet. A bet for Evan to contact his first love, Anna Jordan, and try to win her back. To his surprise, Anna—now the hottest actress in Hollywood—agrees to help him with his foundation. Anna brings her feisty, ninja-like bodyguard along, and suddenly Evan has a problem. The beautiful and tough, Henley Keaton only wants a drama-free Christmas. When Evan Cook calls Henley's employer, to Milwaukee to help with some foundation, she's overjoyed. She can avoid the yearly family fight and eat deep-fried-cheese-curds and relax for Christmas. But when Anna gets sick and forces Henley to go on a date with Evan Cook in her place, Henley’s plan begins to crumble. When Henley and Evan engage in a spirited duel of Shakespeare quotes, things get...complicated. After tragedy strikes, and it looks like Evan's haunted past is going to catch up with him, he must decide if he's willing to walk away or let Christmas miracles come true.