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Fed up with his fluffy articles and the app-based dating scene as well, he strikes a deal with his boss to write a final piece de resistance: How to Lose a Girl. Easier said than done when the girl he meets is Hannah Mayfield, and he's not sure he wants her to dump him. Hannah is an extremely successful event planner who's focused on climbing the career ladder. Her firm is one of the most prestigious in the city, and she's determined to secure her next promotion. But Hannah has a bit of an image problem. She needs to show her boss that she has range, including planning dreaded, romantic weddings. Enter Jack. He’s the perfect man to date for a couple weeks to prove to her boss that she’s not scared of feelings. 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