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.

Joni Lark is living the dream. She’s one of the most coveted songwriters in LA…and she can’t seem to write. There’s an emptiness inside her, and nothing seems to fill it. When she returns to her hometown of Vienna Shores, North Carolina, she hopes that the sand, the surf, and the concerts at The Revelry, her family’s music venue, will spark her inspiration. But when she gets there, nothing is how she left it. Her best friend is avoiding her, her mother’s memories are fading fast, and The Revelry is closing.

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.

After living through a dumpster fire of a Valentine’s Day, Emilie Hornby escapes to her grandmother’s house for some comfort and a consolation pint of Ben & Jerry’s. She passes out on the couch, but when she wakes up, she’s back home in her own bed—and it’s Valentine’s Day all over again. And the next day? Another horrendous V-Day. Emilie is stuck in some sort of time loop nightmare that she can’t wake up from as she re-watches her boyfriend, Josh, cheat on her day after day.