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Holly Would Dream

About The Book

Holly Ross often wishes she lived in a simpler time, when the clothes were glamorous, the men debonair, and the endings happy. That said, her career as a fashion historian isn't so bad. With both a wedding and a big promotion coming up, her own happily ever after seems assured.

So how, in the space of one day, does it all go wrong? How does she end up homeless, jobless, penniless, and fiancé-less? Why is she cruising the Mediterranean in hot pursuit of real estate tycoon Denis King? And why, for heaven's sake, is she chasing down a suitcase full of stolen Audrey Hepburn gowns?

With the sparkling Mediterranean and the eternal city of Rome as the backdrops, Holly's adventures begin to resemble one of the 1950s Hollywood gems she so adores. Finally she must choose between her long-held fairy tale fantasy and a new, real-life dream with an ending she couldn't possibly imagine.

Reading Group Guide

Holly Would Dream
About This Guide

The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion of Holly Would Dream. We hope that these ideas will enrich your conversation and increase your enjoyment of the book. Many fine books from Simon & Schuster feature reading group guides. For a complete listing, or to read the guides online, visit
Questions for Discussion

1. The novel opens with the fairy tale beginning of "Once upon a time..." How is this story a fairy tale? What Audrey Hepburn movie does this opening pay homage to?
2. Holly Ross is a bright, ambitious career woman who seems to have it all. What do you think the attraction was between her and Alessandro? Their breakup turned into a tabloid nightmare and he ends their engagement in a text message. When she asks him to help cancel the wedding arrangements, he refuses like a petulant child. "At that moment, I saw Alessandro, really saw him. He was appearing in the movie of his life and it was about to bomb. Why would I want to costar with such a loser? Was I that afraid to be alone?" What attracted Holly to Alessandro in the first place? Did she really love him? How does this action show Holly who Alessandro truly is? How did Holly miss this before?
3. Real estate mogul Denis King makes quite an impression after he rescues a rain-soaked Holly in true Prince Charming fashion: "A woman could live happily ever after with a man like that. Any guy who would return to help the stranger his car splashed could be counted on to hold your hand when you walked down the street or your hair back when you puked." Why doesn't Holly completely trust Denis? Why do you think she doesn't let on who she is?
4. Conniving Sammie Kittenplatt is a girl who, in Holly's words, was "born with a Kmart exterior that had been attended to by the right dermatologists, hairdressers, trainers, and stylists. Now she was all Bergdorf's." Why is Holly so furious at losing the job to Sammie? After being passed over for the promotion that was rightfully hers, why didn't Holly quit?
5. Holly makes a deal with her boss, Tanya: If she can land a million-dollar benefactor for the museum, she can have the position she wanted. Tanya decides to make it a contest between Holly and Sammie. How does this make both women feel? Who do you think is more qualified for the job?
6. Holly's father laments: "I never should have let you watch those old films. They ruined you for real life." What does he mean by this statement? How are Holly and her father different? How are they alike?
7. When the Hepburn collection is found to be missing from the museum, why doesn't Nigel tell Tanya that Holly is the courier for the clothes?
8. On board the luxurious Tiffany liner, Holly meets wealthy Texas widow Carleen Panthollow. How is Carleen like a fairy godmother to Holly? The oceanic adventure takes Holly to some beautiful ports of call. Which one was your favorite and why?
9. Denis King's engagement to the beautiful Sydney Bass is a merger of two families. Do you think Denis has any real feelings for Sydney, or is he marrying her to please his mother? How does Holly feel about this engagement?
10. Holly Would Dream is filled with hidden secrets and people who aren't what they seem. What did you think of Sydney's behavior on the cruise? Why is the truth kept from Denis? Who is Frank Flannagan?
11. In an effort to create interest in her lectures aboard the ship, Holly chucks her clothes and has the ship's pastry chef decorate her as a live dessert. What was the result? What is it about Holly's personality that allows her to do this? What does this experience show Holly about herself?
12. Holly finally gets to give the "Satan Twins" (Sammie and Tanya) a piece of her mind when she says: "Sammie, I am so sick of you and Tanya telling me I'm not of your world....The difference between a woman of consequence and a nobody has nothing to do with where she is brought up, but how's she's treated. I'll forever be a nobody to you because you treat me as a nobody and always will. But to Denis I'm a woman of consequence because he treats me as one and always will." Which Audrey Hepburn movie does this speech remind you of? What do you think prompted Holly to make this declaration now?
13. When Holly returns to New York, she's invited to attend Denis' opening and does so wearing the ball gown from My Fair Lady. "Wearing fabric that had once adorned Audrey Hepburn was everything I'd imagined and more -- the exquisite detail of the embroidery, the sensual sheen of the organza sheath, the bright sparkle of the thousand tiny crystals. What intoxicating bliss! In this gown, nothing bad could happen to you." Is Holly being herself or playing a part? Does wearing the dress empower Holly?
14. Discuss Holly's transformation and the other characters' development including her father, Tanya, and Denis. How is the ending like an Audrey Hepburn film? Did then ending surprise you?
15. Do you ever wish your life could be like a romantic comedy from the 1950s? What is it about those stories that you find appealing? What does not appeal to you?
16. There are several plot parallels between Holly Would Dream and some old Hollywood classics. In what way is Holly Would Dream like Sabrina, Roman Holiday, How to Steal a Million, Charade, My Fair Lady, An Affair to Remember, or That Touch of Mink?
17. Which movie stars of today come close to having the style and class of Audrey Hepburn and Cary Grant?
18. Do women today still wish for a prince to rescue them and a fairy tale ending or are we too liberated for that kind of thinking?
19. Have you ever encountered people like Tanya and Sammie in a work environment? If so, what was the worst thing a Tanya or Sammie has ever done to you? How do you fight back against snakes like that in the workplace?

About The Author

Photo Credit:

Karen Quinn has tutored scores of children and taught hundreds of parents how to work with their own kids to prepare them for the rigorous kindergarten admissions tests for Manhattan's most in-demand programs.  She has been a featured expert on school admissions on ABC's 20/20 and The View and in The New York Times, Forbes, Redbook, Woman's Day, and more. Karen is also the author of three novels: Holly Would Dream, The Ivy Chronicles and Wife in the Fast Lane. She lives in Miami, FL with her husband and two children. Visit her at

Product Details

  • Publisher: Atria Books (June 3, 2008)
  • Length: 448 pages
  • ISBN13: 9781416573128

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Raves and Reviews

"Delightfully witty and utterly charming, Holly Would Dream will tickle Audrey Hepburn fans more than a Breakfast at Tiffany's and Roman Holiday double feature. Cross my heart and kiss my elbow, I'm just crazy about Holly!" -- Jennifer Coburn, author of The Wife of Reilly

"At last, a beach book with not just a brain and a funny bone but even more critically, a wicked sense that fashion and film and fashion in film are not a matter of life and death. They're more important than that." -- Rachel Johnson, author of Notting Hell

"Clever and charming, Holly Would Dream is the perfect mix of madcap fun and making dreams come true." -- Linda Francis Lee, author of The Ex-Debutante and Ladies Who Lunch

"A delightfully frothy comedy that tweaks high society and Hollywood endings. A fun page-turner of a read that rewards the sharp-eyed film lover with many Hepburn references throughout." -- Jennifer Vandever, author of The Brontë Project

"Funny, romantic, and absolutely charming like the classic Audrey Hepburn movies of the 1950s." -- Heather Graham, actress

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