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When seventeen-year-old Bailey starts a new job at a hotel waterpark, she is less than thrilled to see an old acquaintance is one of her coworkers. Bailey met Charlie a year ago on the long flight to Omaha, where she moved after her parents’ divorce. Charlie’s cynicism didn’t mix well with Bailey’s carefully well-behaved temperament, and his endless commentary was the irritating cherry on top of an already emotionally fraught trip. Now, Bailey and Charlie are still polar opposites, but instead of everything about him rubbing Bailey the wrong way, she starts to look forward to hanging out and gossiping about the waterpark guests and their coworkers—particularly two who keep flirting with each other. Bailey and Charlie make a bet on whether or not the cozy pair will actually get together. Charlie insists that members of the opposite sex can’t just be friends, and Bailey is determined to prove him wrong. Bailey and Charlie keep close track of the romantic progress of others while Charlie works to deflect the growing feelings he’s developed for Bailey. Terrified to lose her if his crush becomes known, what doesn’t help his agenda is Bailey and Charlie “fake dating” in order to disrupt the annoying pleasantries between Bailey’s mom and her mom’s new boyfriend. Soon, what Charlie was hoping to avoid becomes a reality as Bailey starts to see him as not only a friend she can rely on in the midst of family drama—but someone who makes her hands shake and heart race. But Charlie has a secret—a secret that involves Bailey and another bet Charlie may have made. Can the two make a real go of things…or has Charlie’s secret doomed them before they could start?

Meredith Fox has been going to Martha's Vineyard for the summer as long as she can remember. But this summer is the first one back since the death of Meredith's sister. It will all be overwhelming, but even more since since the entire extended family will be together for her cousin's big wedding. Unfortunately, Meredith's longtime boyfriend unexpectedly dumped her two weeks before the wedding, leaving her dateless. Luckily, she has the perfect distraction. Her family has a tradition of playing the ultimate game of Assassin every summer, and this year it will take place during the week of wedding festivities. But her target just happens to be a very cute groomsman. She's determined to not let herself get distracted, not let herself be lost in another doomed relationship. But as the week progresses, she can't help falling for him, which may cost her not only the game, but also her heart. Meredith's family's annual game of assassin at Martha's Vineyard during a summer wedding is the perfect chance to honor her sister's legacy, and finally join the world again. But when she forms an alliance with a cute groomsman, she's at risk of losing both the game… and her heart.