Twenty Boy Summer

Twenty Boy Summer is a 2010 young adult fiction novel and the debut book by author Sarah Ockler. It tells the story of two teenage girls who try to meet one boy on each day of their summer vacation.

Frankie and Anna are best friends. They decide to spend twenty days of their summer break in Zanzibar Bay, California, a fictional town situated two hours south of San Francisco. They’re joined by Frankie’s parents. Frankie is excited for Anna to meet her first boyfriend and plans for them to meet a new boy on each day of their twenty-day vacation. While Anna is a virgin, she has had a boyfriend before. In fact, she fell in love with Frankie’s brother, Matt, the previous summer, but kept their tryst a secret from Frankie. Tragically, Matt died in an accident about a year earlier.

This puts Anna in a very uncomfortable position: She doesn’t want to tell Frankie about her affair with Matt because it will open old wounds for both of them. On the other hand, it is difficult for Anna to feign excitement about any of the boys the pair meets because she believes none of them can possibly compare to Matt. On a more explicit level, Frankie—who has already lost her virginity—hopes Anna will do the same on this trip, which would bring the two closer together. But Anna cannot imagine losing her virginity to anyone but Matt. Because he is deceased, this puts her in a rut she feels she cannot escape.



The first few boys they meet are nothing to write home about, as Anna expected. But then Frankie and Anna meet two surfer boys named Jake and Sam. Anna assumes that Frankie and Jake are having sex. Meanwhile, Sam tries to forge a connection with Anna, but it is very difficult for her to overcome her feelings for Matt. Frankie’s parents are also so overcome by grief that they don’t notice the girls are out every night with boys.

In addition to being more sexually active than Anna, Frankie also drinks a lot more than her friend does. Frankie’s behavior while drinking causes a great deal of conflict between the two girls. Things come to a head when Frankie surreptitiously reads Anna’s diary after a night of drinking and partying. Frankie learns about Anna’s feelings for Matt, which turned into love when Matt kissed her on her fifteenth birthday. This opens old wounds for Frankie, who hasn’t properly dealt with her brother’s death. She angrily throws Anna’s diary, along with all the pictures of Matt and Anna, into the ocean.

While Anna feels betrayed, Frankie feels a strange sense of jealously. She tells Anna, “He was my brother. Mine. You have no right to have anything left of him.”



Although the book is called Twenty Boy Summer, Anna actually meets fewer than ten boys. After meeting Sam—whom Anna genuinely likes despite her grief over Matt—Frankie stops trying to hook Anna up with new boys. That grief turns out to be a double-edged sword, however, because it also makes Anna feel guilty about the affection she feels toward Matt. Compounding the guilt are her feelings of remorse for hiding her relationship with Matt from Frankie.

One of the major pieces of symbolism in Twenty Boy Summer is sea glass. In years prior, when Frankie and Matt would go on summer vacations to Zanzibar Bay without Anna, the pair would bring back sea glass for Anna. The glass represents the characters’ wounded hearts: beaten, battered, and shattered by violent waves, yes, but also transformed by the struggle into something arguably more beautiful than before. Through this symbol, the characters grapple with the pain and trauma of grief and broken hearts, as they learn to appreciate the wisdom and experience that comes from having loved and lost.

In the end, the characters are able to move on from the trauma of Matt’s death while still honoring and remembering this beloved individual, reserving a special place in their hearts for him even as they make room for new people. Ockler beautifully summarizes this struggle in the following quote: “Sometimes I think we all feel guilty for being happy, and as soon as we catch ourselves acting like everything is okay, someone remembers it’s not.”