Everyone at the Bexley School believes that Sage Morgan and Charlie Carmichael are meant to be. Even though Charlie seems to have a new girlfriend every month, and Sage has never had a real relationship, their friends and family all know it's just a matter of time until they realize that they are actually in love. When Luke Morrissey shows up on campus his presence immediately shakes things up. Charlie and Luke are drawn to each other the moment they meet, giving Sage the opportunity to spend time with Charlie's twin brother, Nick.

Lily Hopper has two more weeks until she's officially finished with boarding school. With graduation quickly approaching Lily is worried that she's somehow missed out on the fun of being in high school. So, when she receives a mysterious note inviting her to join the anonymous senior class Jester in executing the end-of-year prank, Lily sees her chance to put her goody-two-shoes reputation behind her. When Lily realizes the Jester is none other than Taggart Swell, her ex-boyfriend, she's already in too deep to back out. Lily might've dumped Tag, but she still has major feelings.

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.

Macy Descanso is a writer. Who cares if her bestselling-author mother pulled some strings to get her into a prestigious writing retreat? Macy belongs here. Even when the coordinators unexpectedly announce that this year’s theme is romance, Macy—a total cynic—is up for the challenge. But she’s not prepared for her critique partner to be fellow publishing nepo baby Caleb Bernard. While Caleb may be what most romance writers would describe as “swoony,” he’s off-limits, because the Descansos and Bernards have beef.

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.