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There are two kinds of people on the island -- those who leave at summer's end...and those who are left behind.

For seventeen-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.

And when the Barclays, a wealthy summer family, offer Winnie an additional babysitting job in the evenings after work, she jumps at the opportunity. Little Cassie Barclay is fun to take care of, and hanging out in the gorgeous Barclay summer house overlooking the harbor is far more pleasant than being on the front lines of the battle between her parents.

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. Winnie soon discovers that life in the Barclay summer house isn't so perfect after all, and what was supposed to be a carefree summer escapade is quickly becoming more complicated than she ever thought possible....

288 pages, Paperback

First published June 24, 2008

13 people are currently reading
1598 people want to read

About the author

Jenny O'Connell

9 books254 followers
Published chick-lit under the name Jennifer O'Connell.

I haven't been called Jenny in years (thankfully), but I thought it was fitting to publish my teen book under the name that still makes me think of high school.

My high school days may be long behind me, but I have a lot in common with Vanessa, the main character in PLAN B. Like Vanessa, I also went to a small private school. I was also mildly obsessed with college from fifth grade on, thanks to a book I read in which one of the characters went to Dartmouth. But unlike Vanessa, my brother wasn't a TV star. And he didn't drive me crazy. I actually still like him. As for creating a How To guide for guys, like Emily does in THE BOOK OF LUKE, I can't say that I know enough to write an entire guide, but I did have a blast writing the tips at the beginning of each chapter. And I wish a guide like this did exist when I was in high school (and college and even after that!).

Last summer I was on Martha's Vineyard doing research for my upcoming Martha's Vineyard Novel series (tough job, but somebody’s got to do it). I hope this books capture what I love so much about the island

Although she's written about a reality dating show, a prescient pastry chef, and a woman who inspired an 80's rock hit, Jennifer has not spent hours dissecting The Bachelor, she can barely follow the directions on the back of a Betty Crocker box, and she can only dream of a long-haired, guitar-thrashing rocker even giving her a second glance.

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5 stars
214 (29%)
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225 (30%)
3 stars
209 (28%)
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61 (8%)
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18 (2%)
Displaying 1 - 30 of 31 reviews
Profile Image for Stephanie.
405 reviews16 followers
March 20, 2017
This book was a nice, light summer, Sarah Dessen-esque read. The beginning was a bit slow, I have a 50 page rule, in which if the book still sucks by the 50th page, I'll put it down, but luckily this book picked up a little bit before then. It was definitely more of a realistic contemporary YA-Novel. If I just saw this book on the shelf, by looking at the title and cover, I would have walked right passed it. But having read "The Book of Luke" by Jenny O'Connell in the past, and loving that, I decided to give this book a chance. I still like the Book of Luke better, but Rich Boys was definitely good!

I fell in love with the characters, especially little Cassie, and of course, Jay. Not to mention that Winnie and Jay's relationship felt completely natural to me. I liked the way the story ended, it felt very authentic. I really liked how Jenny O'Connell described certain settings, I actually felt like I was on the Island with Winnie. The plot of this novel, was nothing extremely shocking or new, but it was well told, although I think that was thanks to the very like-able characters. Great book!
Profile Image for Kelly Oram.
Author 34 books4,375 followers
September 28, 2010
So I spontaneously picked this out of a clearance bin at Borders the other day. (I can't go to Borders without picking something up. It's a compulsive behavior that really borders on obsession.) I'd never heard of this book and never read anything by Jenny O'Connell before so I didn't know what to expect, but hey, it was three bucks. Plus, I was curious because I've had "The Book Of Luke" on my to-read list for a while.

I was very pleasantly surprised. This is exactly the kind of book I like to read if I'm in the mood to get away from fantasy and just spend some time in a normal teenager's dramatic life. "Rich Boys" kept me interested from start to finish. I loved how Jenny O'Connell painted the scene. I was transported to that beautiful island without being bogged down by it. I actually felt like a local at times and got annoyed by the tourists lol.

The story was nothing all that new plot wise, but it was very well told with extremely likable characters. The drama felt important and heavy without ever feeling too melodramatic. Over-all I thought the book had a very Sarah Dessin feel. I really enjoyed it and look forward to reading more from Jenny O'Connell in the future. I guess I need to move "The Book Of Luke" higher up on my list now.

The one think that bugged me though, was the title. I can't understand why it's called "Rich Boys". I think that's a little misleading to the story. I mean yes, the boys in the story are totally loaded, but the story really has nothing to do with that. The money is more just part of the setting than the plot. I think this story would be more appropriately titled "Summer Boys" because instead of stressing about the fact that the guys in the book have money when the girls don't, the girls are way more concerned that the guys are only on the island for the summer. That's really what this book is about. That one special summer of romance...

Profile Image for Sara.
1,627 reviews74 followers
August 16, 2008
The second book in the "Island Summer" series. I didn't know what to expect from this book, since the series is not focused on one character in particular but rather has the island itself as the main character and this book's narrator is one only introduced in passing in the first book. But, it totally works. And I totally loved this book more than I did the first, which I didn't think would happen.

In this, Winnie takes a job babysitting a young girl for a family summering on the island, trying to make extra money. It seems really cushy until the girl's older brother arrives unexpectedly and starts causing trouble around the house because he has lingering anger over a lot of family issues.

What I loved about this book is that it didn't shy away from any tough issues or conversations. Winnie thinks at first that the family is perfect, then she thinks that the brother who's arrived is just a jerk, and then she starts realizing that there is a lot she doesn't know about the family situation and that so much left unsaid is causing so many problems. The growing relationship between Winnie and Jay (the brother) is done so gracefully and smoothly; one of the best written teen relationships I've read, in fact. Winnie sees Jay at his worst, they force each other to confront real problems, and Winnie sees the good and the bad to him and everyone else around them. Things aren't painted as simply black and white, and I love the book's overall message of how things may not always be easy or simple but that doesn't mean they're not worth doing. I thought this was such a sweet book that shows both relationships, friendships, and family relationships in a very well done way.
25 reviews
June 17, 2009
Rarely do I ever give books 5/5. I gave this one a 5 though because it was so real! It could happen to anybody, you aren't reading about wolves or vampires of wizards or dragons or talking birds or whatever else may be out there (I have nothing against vampires, wolves or wizards) In Rich Boys, it's about a girl named Winnie and she has this summer job were she meets this mom who asks her to babysit her daughter for her. The job is easy, the kid is sweet but, they step-son, Jay, is a handful. Jay portrays himself at first to be the tough guy, you may not like him at first but give him a chance. I did. So, Winnie try's to communicate with Jay and one day they end up having a real conversation. Soon, Her friends, Jay and Winnie start to hang out and Winnie really falls in love with this guy. The drama, the love and the care they share for each other and their friends is what really makes the book very interesting!
Profile Image for Valerie.
927 reviews437 followers
May 30, 2011
Ignore the cover and ignore the title, this book is very different than both of those things. I like Jenny O'Connell books and this one is good. It deals with a lot of family problems as Winnie tries to cope with changes in her parents relationship. She's not the only one struggling with that, Jay is trying to overcome his mother's death and rebuild a relationship with his father. Together, they try to work through things.

I would have given this book a better rating but there was one little thing that I couldn't get over. My Christian values couldn't get past the way that abortion was handled in this book. I won't say anymore, just know that the topic comes up about 2/3 through the book and I didn't like how things were portrayed.
Profile Image for Maddie.
373 reviews3 followers
July 27, 2021
This book was really wholesome and mysterious at the same time. It is such a good time capsule, transporting you to 2008 summer on that island one ferry ride away from Boston, that houses all these sweet, heartbreaking, hopeful moments created between people who are trying their best with and grappling with situations that they don't always understand. The story of love between our leads was at the heart of this book, and even though their fate was left a mystery, going by what we've seen of them so far, they're definitely going to make it, far more than just okay, be a support to everyone around them, especially to little children, going to be producing some of their own for sure who're going to be well taken care of and lucky to have these two quiet dependable people as their parents.
Profile Image for Dorothy.
74 reviews1 follower
December 27, 2010
I was wondering if Jenny O’Connell has a new book out when I found myself on the Goodreads page for Rich Boys. It’s a shame that not enough people know about this author and her books. I have all four of Jenny’s books and I can say with certainty that she is a gifted YA writer. Her work is much better than most YA contemporary romances out there. HOWEVER. I don’t entirely blame people for not wanting to give her books a chance. They all seem to suffer from the same thing: a bland title and a misleading cover. Take this one for example. Rich Boys, really? What kind of unimaginative and uninspired title is that? It does a great disservice to the book because it makes you think of the wild rich kids from the defunct TV show Laguna Beach when it hardly has anything to do with the lives of the rich and famous. (On second thought, her books are published under MTV so maybe this was done deliberately? I sure hope not.) What about the cover photo? You will not normally find me complaining about half-naked surfer boys. Sure, they’re nice to look at, but would I read a 250 page book about them and their exploits? No. The bigger problem? Surfing isn’t even a part of the story. It’s set in summer. There is an island. There is water. There are sandcastles. There is no surfing. Change the cover and come up with a title that’s closer to the storyline and Jenny O’Connell might be the next Jennifer Echols, one of MTV’s more prominent authors.

Rant aside, Rich Boys is very memorable for me because I was reading it at the same time I was studying for my first Philo orals. That was a little more than two years ago. I was distracted to say the least, but I will not blame it for my poor midterm grade. It wasn’t the book’s fault that I had little self-control. Nor was it Jenny O’Connell’s fault that I kept my head buried in her book even when a pile of Philosophy readings was calling my name. I applaud her for tackling a topic not often told in YA stories, much less YA romance. Separation. This isn’t entirely what the book is about, but it was the one that stood out the most for me. It has depth that is unfortunately not conveyed in its title or cover. It’s a little short for a Sarah Dessen novel but it’s almost of the same caliber. If you’re looking for little known underrated YA books to while away the time, I highly recommend you give this a try. If you like it, try O’Connell’s earlier YA novel, another one of my favorites, The Book of Luke.

Favorite lines:

“I thought absence was supposed to make the heart grow fonder.”
“I guess it can. It can also make the heart forget.”

“I guess I could force him to stay, tell him if he goes, it’s the end, but what does that prove?... He’s got to see if he can do it. And I’ve got to let him try. Otherwise, what’s the point?”

“Until next time.” [Gah! For a long time this was my absolute favorite line from any book. It’s so full of hope and longing and love. These are three little words that imply there was a past and it was good enough, worth it enough, for two people who have to be apart to make plans for the future. For next time. It’s perfect. <3]
Profile Image for papalbina.
593 reviews265 followers
November 17, 2010
«There are two kinds of people on Martha's Vineyard, the ones who leave at summer's end... and those who are left behind»

The melancholic ending left a bitter-sweet taste in my mouth and an unbearable eagerness to know what happens after that with these two. Was that supposed to be promising?? Is this story going to continue or just ended at the end of the summer? Is the lighthouse a promise or just a final goodbye? I want to think yes, there's more story after that, but I would rather read it than imagine it. Winnie (or Jay) not crying in such moments made me want to cry myself T-T

The main character, Winnie, is still being a mystery for me. I couldn't figure her out. At the beginning she is quite self-confident, but towards the end she goes down, "deflates". I suppose Winnie was left half-developed in order to get other characters forwards.

The best part of the book: the conversations between Herb and Fred, nice!! ^___^

I should begin to worry about myself, especially if I enjoy this kind of books more now than when I was supposed to be reading them fO.o I'm like 15 years late ¬¬
Profile Image for Jessica.
58 reviews10 followers
April 23, 2013
This book hit the spot.

Winnie lives on the island year round, but this tourist season she gets a change up when she starts working for the Barclays a few days in the afternoon. The Barclays seem great. Anne is very nice, but overwhelmed by pregnancy and Cassie is the easiest kid to take care of. The only problem is her 19-year old moody brother,Jay. When Jay announces that he will be summering on the island, the easy feel in the house all but vanishes replaced by the tension that Jay carries with him. Winnie's summer just got more complicated than she could have planned for.

Yes, this is a slightly simple, very predictable book, but after crying my eyes out and being depressed for the past three books I needed something on the lighter side. This book was the perfect sunny afternoon beach read. Winnie is a little unrealistic in her need to fix things, but Jay seems cute and charming when he wants to be.
Profile Image for Devz Milady.
326 reviews5 followers
September 19, 2015
Okay, so to be honest I didnt finish the book.
After reaching around page 84 and sleeping off twice in the middle and yawning a lot, I decided that if a YA 'romance' novel is so boring as to induce sleep in the 1st 50 pages, then it mostly likely aint worth pursuing...

As far as I can see, our heroine Winnie is a nice intelligent quick-to-reach-assumptions girl who is boy-free and waiting for her knight..
Our hero Jay is the eternally troubled angry young man, misunderstood by his family and everyone else brooding on the unfairness of it all..
And we also our sidekicks Jessie, whose inability to see a possibility cheating Nash is a good background for the awesomeness of the future relationship between Jay and Winnie..

And yawn... the rest of the novel is so boring filled with craft ideas, descriptions of summer homes, school stuff and yaawwwn..

I suggest you pick this as a sleep inducing one for a bad plane trip.
Profile Image for Sarah Anne.
1,881 reviews190 followers
February 11, 2013
Since I didn't read the first one, my criticism might not make sense BUT I feel that the Jay and Winnie's relationship was too rushed. Also, I found Jay's attitude towards Winnie rapidly change, going from cold and distant to all of a sudden I don't want to leave you, and as a reader, I didn't have anytime to wrap my head around it before BAM, they were together. But on the plus side, who doesn't like a story where the good girl with problems helps straighten out the bad boy? Plus bonus points for a summer romance.
Profile Image for Christine Alibutud.
521 reviews85 followers
Want to read
February 1, 2014
Ughhhh I really want to read this!!!!
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But the sad truth is I'm broke and I can't purchase the ebook!!!!!!!! Infinite creys so much!!!
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Profile Image for Tigrish.
578 reviews13 followers
July 17, 2013
This book is definitely for the younger side of the young adult genre. Although it's a nice sort of coming of age story and the writer offers some good insights, it was just a bit on the boring side for me. But it's not like it was advertised as something action-packed so I guess for what it represents, it did a pretty good job. This writer at least is pretty good.
22 reviews
April 16, 2011
completely loved this book! It's relate-able and gets you excited whenever Jay came up!! But the end didn't excite me as much. I honestly was a little disappointed and expected more! but as a whole it was a really fast and great read.
2 reviews1 follower
September 4, 2011
I thought this book was wonderful but the title was very misleading. should be called "summer boys". The ending leaves you wondering what's going to happen between Fred and herb. hope we will get to find our.
Profile Image for Daphne.
214 reviews19 followers
October 25, 2012


This was an excellent book that was far more than the title implied. I was expecting a fluffy book but in fact was pleasantly surprised with a book full of emotion and self discovery. As a matter of a fact "Rich Boys" hardly does the book justice.
2 reviews
May 17, 2013
At first, I though the first few chapters were a fluff and I still do. But, upon finishing the book, I found myself crying. It is a beautiful book. I love how it showed how true love goes beyond mere distance. I love it. Worth the read!
Profile Image for Lance V.
14 reviews
August 26, 2010
It was not exactly what I had first thought as I was reading its cover. Even so, I got engrossed reading every detail. *thumbs up*
Profile Image for Jade.
79 reviews
July 9, 2011
It was a good, summer fun readi.
5 reviews
May 9, 2011
LOVE LOVE LOVE!!! This book was Awesome i loved the characters and the whole story line, especially the romance between Winnie and Jay!!
Profile Image for Carolina.
124 reviews80 followers
May 5, 2012
This book felt so real to me, I loved it.
42 reviews6 followers
November 5, 2012
Brilliantly written, a great story. Loved it as much as the first one.
Profile Image for Sophie.
5 reviews1 follower
January 12, 2015
I thought this book was ok, but not my favourite. I loved the storyline but I didn't think it was very well written and I don't think the book was ended very well. Overall a cute summer read.
Displaying 1 - 30 of 31 reviews

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