A country boy looking to win his best friend's heart. A waitress afraid of giving hers away. And one crazy, impromptu dating plan that's about to change everything. Ex-model Livy Hensley has exactly three talents: making coffee, landing herself in the most awkward moments known to man, and failing miserably at relationships. But when the sweetest southern boy on the planet offers to be your dating coach, who could say no? Between struggling to open a café and trying to atone for a consequence of her past, Livy can use all the help she can get. Besides, what could possibly go wrong on a few practice dates with your best friend? Chase Thompson's no stranger to hard work. If that's what it takes to prove to Livy they should be together, then he's all in. He can handle pretending he's not hopelessly in love with her. Sort of. Almost. Okay, nowhere close. But with a conflicting solution to his family's greatest trial on the line, the stakes of keeping his dating coach plan from backfiring have never been higher. Up against the countdown of choices, Chase and Livy must find the courage to risk what they fear most for the someday they've always hoped for.