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.

The annual family vacation to Martha's Vineyard seems like the perfect place to reconnect. Her entire extended family is gathering for a big summer wedding, and although Meredith is dateless after being unexpectedly dumped, she's excited to participate in the traditional Fox family game of assassin that will take place during the week of wedding festivities. Claire always loved the game, and Meredith is determined to honor her legacy....