"The Boyfriend List" by E. Lockhart

They say you have to kiss so many frogs before finding your prince. Ruby Oliver begins seeing a therapist after the emotional trauma of being dumped by her first serious boyfriend of eight months, who is truly more of a frog than a prince for the reason that he dumps her and begins dating her best friend.

As if fifteen year-old Ruby isn’t upset enough over losing her boyfriend and her best friend of ten years, a series of events cause Ruby’s social life to start spiraling downwards in a number of days as she:
1. [Does] something suspicious with a boy.
2. [Does] something advanced with a boy.
3. [Has] an argument with a boy.
4. [Drinks] her first beer (someone handed it to her).
5. [Gets] caught by her mom.
6. [Loses] a lacrosse game.
7. [Fails] a math test.
8. Hurt[s] Meghan’s feelings (even though they aren’t really friends).
9. [Has] graffiti written about her in the girls’ bathroom.
10. [Loses] all her other friends (Nora and Cricket).
11. Become[s] a social outcast.
What would you do if you were fifteen, were dumped by your first serious boyfriend, lost all your friends, and fell out of favor in the eyes of all your peers at school? Ruby begins having panic attacks, which her parents find worthy of a series of visits with a therapist named Doctor Z. On account of her troubled love life, Doctor Z assigns Ruby the task of making a list of “all the boyfriends, kind-of boyfriends, almost-boyfriends, rumored boyfriends, and wished-he-were boyfriends” she has had. Ruby decides on fifteen guys for her “Boyfriend List”:
1. Adam (but he doesn’t count.)
2. Finn (but people just thought so.)
3. Hutch (but I’d rather not think about it.)
4. Gideon (but it was just from afar.)
5. Ben (but he didn’t know.)
6. Tommy (but it was impossible.)
7. Chase (but it was all in his mind.)
8. Sky (but he had someone else.)
9. Michael (but I so didn’t want to.)
10. Angelo (but it was just one date.)
11. Shiv (but it was just one kiss.)
12. Billy (but he didn’t call.)
13. Jackson (yes, okay, he was my boyfriend. Don’t ask me any more about it.)
14. Noel (but it was just a rumor.)
15. Cabbie (but I’m undecided.)
Reading about Ruby’s secret crushes, the boy who left gummy bears in her mail cubby in fourth grade, the boy she was teased about being in love with by all the other kids at school, the boy who pretended he wanted to be her boyfriend but was dating someone else, her first (bad) kiss, her first (good) kiss, and her first 24-hour boyfriend will undoubtedly spark fond memories for female readers.