Ruby Oliver is 15 and has a shrink. She knows it’s unusual, but give her a break—she’s had a rough 10 days. In the past 10 days she:
lost her boyfriend (#13 on the list),
lost her best friend (Kim),
lost all her other friends (Nora, Cricket),
did something suspicious with a boy (#10),
did something advanced with a boy (#15),
had an argument with a boy (#14),
drank her first beer (someone handed it to her),
got caught by her mom (ag!),
had a panic attack (scary),
lost a lacrosse game (she’s the goalie),
failed a math test (she’ll make it up),
hurt Meghan’s feelings (even though they aren’t really friends),
became a social outcast (no one to sit with at lunch)
and had graffiti written about her in the girls’ bathroom (who knows what was in the boys’!?!).
But don’t worry—Ruby lives to tell the tale. And make more lists.
About the Author
Read an Excerpt
1. Adam (but he doesn't count.)
Adam was this boy that I used to stare at in preschool. His hair was too long, that's why. It stuck out behind his ears and trailed down his neck, whereas all the other five-year-old boys had bowl haircuts. I didn't have too much hair myselfit didn't grow fast and my mom was always trimming it with her nail scissorsso I was a little obsessed with hair.
Adam's last name was Cox, and after I had been eyeing him for a couple of months, I named this stuffed bunny I had after him. All the grown-ups laughed when I said the bunny's name was Cox, and I didn't understand why.
Pretty soon, Adam and I were playing together. Our parents took us to the zoo, and we'd spend time after school in the nearby playground, drawing with chalk and walking up the slide. I remember we went swimming a few times at the YMCA, and hung out in a plastic wading pool in his backyard. His cat had kittens, and I got to help name them because I came over the same morning they were born.
And that was it.
We were only five years old.
When I was old enough for kindergarten, I started at Tate Prep and he went somewhere else.
Doctor Z looked down at the Boyfriend List. She didn't seem too impressed with my Adam Cox story. Or maybe it was the list itself she didn't think much ofthough it had taken me a lot of work to do. I started the night after our first appointment, in bed in my pajamas, writing on this thick, cream-colored stationery my grandma Suzette got me. It says Ruby Denise Oliver on the top in this great curlicue fontbut I never use it, since anyone I'd want to write to has e-mail.
My first draft, I only wrote down Jackson and Cabbie. Then I added Gideon at the beginning, with a question mark next to his name. Then Michael, the guy who was my first kissputting him in between Gideon and Jackson.
Then I turned off my light and tried to go to sleep.
Well, I wasn't sleeping well lately anywaybut I lay there with this feeling that the list wasn't finished. I remembered that I'd told Doctor Z about Angelo already, so I turned the light back on and squeezed him in between Jackson and Cabbie.
Oh, and I had mentioned Noel to Doctor Z, toothough we were only friends. I stuck him in right after Jackson, just to have somewhere to put him. Then I rewrote the list in nice handwriting and managed to get myself to sleepbut in the middle of the night I woke up and wrote down two more boys and my History & Politics teacher.
Then I crossed them all out.
At breakfast the next morning, I jumped up from my cereal bowl and put one of them back on.
At school, the hallway by the mail cubbies suddenly seemed like an obstacle course of old crushes and rejections. Shiv Neel. Finn Murphy. Hutch (ag). All three in my face before I even got to my first class. I pulled out the list and wrote them down.
All day long, I thought about boys. (Well, even more than usual.) And the more I thought, the more I remembered.
Adam, the mermaid.
Sky, the jerk.
Ben, the golden boy.
Tommy, who surfed.
Chase, who gave me the necklace.
Billy, who squeezed my boob.
Never in a million years would I have expected the list to be anywhere near so long. But by the end of the day, there were fifteen names on there, and the list was all scribbly-looking, with arrows zooming around to show what order the boys should really go in.
It was a mess, so during geometry I recopied it on the stationery in my best writing and threw the old one away.2 Then I tucked it into a matching envelope to give to Doctor Z.
"Why did you stop playing with Adam?" Doctor Z wanted to know.
"I told you, I started a different school."
"Is there something more?" she said, looking at me over those red-rimmed glasses.
I had liked making the list, it was kind of fun. But ag. What was the point of talking about something from ten years ago that wasn't even important? Zoo trips with Adam Cox and his mom weren't exactly significant to my mental development.
Not that there was anything else I wanted to talk about.
I just wanted the panic attacks to stop.
And the hollow, sore feeling in my chest to go away.
And to feel like I could make it through lunch period without choking back tears.
And Jackson. I wanted Jackson back.
And my friends.
"Did you ever see him again?"
"Who?" I had forgotten what we were talking about.
Reading Group Guide
1. After the Adam "debacle" in chapter one, Roo and Kim begin a notebook called The Boy Book in which they write down everything they know about boys. Have you ever started a book like this on your own or with your friends? Do you think it would be useful? What information would you include?
2. On page 41, Ruby spills her guts to Kim about Finn. Is this smart? Are there circumstances in which it’s better to keep your mouth shut? Has something like this ever happened to you–you tried to do the right thing and it backfired?
3. Ruby gives three examples of the way love works in the movies. In her example on page 64, the couples hate each other half the time but still get together in the end. In her example on page 65, the couple breaks up, but then the man realizes that he loves the woman and can’t exist without her, and they get back together and live happily ever after. And on page 198, the hopeless dorky guy who’s been there all along eventually gets the girl. Do you agree with Ruby that these happy endings don’t happen in real life? Pick one of the movies mentioned and discuss it. Does the romantic situation in the movie ring true? Can you think of other movies, books, or television shows that would fit on Ruby’s lists?
4. Ruby discovers that dating Jackson isn’t the way she thought dating was supposed to be. Have you ever discovered that your ideas about something were wrong? How was the reality different from what you had imagined?
5. In chapter six, Kim and Ruby invent the perfect boyfriend and name him Tommy Hazard. Do you have your own Tommy Hazard? Are there hazards in creating a "perfect" boyfriend?
6. After stealing Jackson, Kim tells Ruby, "When you find your Tommy Hazard you’ll understand. I honestly couldn’t help it." Doyou agree with Kim’s justification of her behavior? Does she dothe right thing?
7. Even though Noel has become Roo’s only ally, she turns on him on page 176 after he says, ". . . if those are your friends you’ve got no need for enemies." Why does this upset Ruby so much? Do you think Noel is right? Why is Ruby not yet ready to give up her old life, even though it has become the source of such pain?
8. When Kim calls Ruby a slut in class, Mr. Wallace gives a lecture on the negative effects of labels and points out that "there are no equivalent epithets for men whatsoever, and didn’t that say something about how women are viewed in our culture?" (page 177). What does it say? Can you give examples of the negative effects of labels, from real life or from movies, music, television shows, or books?
9. Ruby ends the book by saying, "I was out of the Tate universe, standing on the edge of the sea" (page 229). What does she mean by this? Is she really out of the Tate universe? Is this a satisfying ending? Do you believe that Ruby is in a better place now than when the book began? What do you think is next for her?