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Brandy Zulueta is no amateur when it comes to love. She's had her strings of bad romance, asshole ex-boyfriends, and toxic relationships. That's why she has given up on finding the one. At 38, she is content to be single, devoting all her time and attention to her B&B. This is her home; her guests are her family. Until she meets Brody Nuyda, who sweeps her off her feet and makes her believe in romance again. At 40, is living his best life--single and free of all responsibilities, he owns and manages several businesses, and gets relationship benefits from different girls sans commitment. Then he meets Brandy, who makes him rethink his choices in life. Both scared of taking risks and falling in love, they mask their true emotions with competitiveness and business strategies. But in the end, Brody and Brandy that they would only end up hurting themselves and each other if they held back their feelings. Both learn that they need to gamble again in order to win.