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.

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.

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.

Perpetual daydreamer Liz Buxbaum gave her heart to Michael a long time ago. But her cool, aloof forever crush never really saw her before he moved away. Now that he’s back in town, Liz will do whatever it takes to get on his radar - and maybe snag him as a prom date - even befriend Wes Bennet. The annoyingly attractive next-door neighbor might seem like a prime candidate for romantic-comedy fantasies, but Wes has only been a pain in Liz’s butt since they were kids. Yet, somehow, Wes and Michael are hitting it off, which means Wes is Liz’s in.