Emily Abbott has always been considered the Girl Most Likely to Be Nice - but lately being nice hasn't done her any good. Her parents have decided to move the family from Chicago back to their hometown of Boston in the middle of Emily's senior year. Only Emily's first real boyfriend, Sean, is in Chicago, and so is her shot at class valedictorian and early admission to the Ivy League. What's a nice girl to do?Then Sean dumps Emily on moving day and her father announces he's staying behind in Chicago "to tie up loose ends," and Emily decides that what a nice girl needs to do is to stop being nice....
For 17-year-old Winnie, summer can't arrive fast enough - anything to get out of the house and escape the cold war brewing between her parents. With her older sister, Shelby, spending the summer in Boston, Winnie's left to deal with the situation all by herself. Which is why she's happy to spend all day away from home at a cushy job - camp counselor at the prestigious Oceanview Inn. Then Cassie's older and devastatingly attractive stepbrother, Jay, arrives on the island after a disastrous first year at college, and he seems to want nothing more than to wreak havoc for his stepmother and the rest of his family.
There are two kinds of people on the island -- those who leave at summer's end...and those who are left behind. Kendra and Mona are best friends, local girls who spend their summers catering to rich tourists and the rest of the year chafing against small-town life. Then Mona's mom marries one of the island's rich summer visitors, and Mona joins the world of the Boston elite, leaving Kendra and Martha's Vineyard behind. When Mona returns the following summer, everything is different. Now Mona spends her days sunbathing with her private-school friends, while Kendra works at The Willow Inn -- a job she and Mona once hoped to do together. Unlike his sister, Mona's twin brother Henry hasn't changed. He's spending his summer the way he always has: with long, quiet hours fishing. Early mornings before work become special for Kendra as she starts sharing them with Henry, hoping he can help her figure Mona out. Then Kendra hatches a plan to prove she's Mona's one true friend. She'll uncover the identity of the twins' birth father, a question that has always obsessed Mona. And so she sets out to unravel the seventeen-year-old mystery of the summer boy who charmed Mona's mother. But are some secrets better off staying buried?
Vanessa has the next year of her life pretty much figured out. Sure, there's some parental convincing to do but she and her celebrity-obsessed gal pal Taylor pretty much think their plan is airtight. Then Vanessa's parents get a mysterious phone call and drop a bombshell on her that she never could have imagined. She has a half-brother. And he's coming to live with them.