Cassandra O’Leary Books in Order

Picture an Australian storyteller who turned a chance encounter on a flight into a swoon-worthy romantic comedy—meet Cassandra O’Leary! This award-winning author has captured hearts with her witty,...

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Picture an Australian storyteller who turned a chance encounter on a flight into a swoon-worthy romantic comedy—meet Cassandra O’Leary! This award-winning author has captured hearts with her witty, heartfelt, and steamy novels, blending humor and romance with a distinctly Aussie flair. Known for her Girl on a Plane series, O’Leary is a rising star in contemporary romance, crafting stories that make you laugh, cry, and believe in love.

Born in Dandenong, Victoria, O’Leary’s journey from corporate communications to romance novelist is as inspiring as her books. With a knack for creating relatable characters and glamorous settings, she’s become a beloved voice in romantic comedy, proving that love can spark anywhere—even at 30,000 feet.

The Making of Cassandra O’Leary

Growing up in Melbourne’s south-east suburbs, Cassandra O’Leary was always a dreamer, devouring books and dreaming of far-off places like Italy and Spain. After graduating top of her class with a Bachelor of Communications from Monash University in 1998, she built a successful career as a communications professional, working with organizations like RMIT University. But her true passion lay in storytelling, inspired by authors like Marian Keyes and Christina Lauren. In 2014, she took a leap into fiction, entering writing competitions and honing her craft, which led to her breakthrough moment: winning the global We Heart New Talent contest by HarperCollins UK in 2015.

Now a proud member of Romance Writers of Australia and the Melbourne Romance Writers Guild, O’Leary balances her writing career with life as a mother of two high-energy “mini ninjas” and wife to her “superhero” husband. Her real-life adventures and family anecdotes often sneak into her stories, adding authenticity and warmth.

Cassandra O’Leary’s Unforgettable Stories

O’Leary’s debut novel, Girl on a Plane (2016), is a steamy, emotional romp that follows feisty Irish flight attendant Sinead Kennealy and Australian CEO Gabriel Anderson as sparks fly during a turbulent journey from Melbourne to London. Praised for its sizzling chemistry and laugh-out-loud moments, it became an iBooks top 20 bestseller in the UK and Australia. The Girl on a Plane series continues with novellas like Girl Under the Christmas Tree and Girl on a Layover, each delivering cozy, heartwarming romance with a holiday or travel twist.

Beyond the series, O’Leary’s indie-published works like Hot in the City, a collection of short romantic comedies, and Dating Little Miss Perfect showcase her versatility. Her writing style is a delightful mix of sharp wit, tender emotion, and vivid settings, often set in her hometown of Melbourne or exotic locales like Singapore and Paris. Themes of love, independence, and overcoming personal challenges resonate throughout her work, making her characters feel like friends you’d meet for coffee.

O’Leary’s ability to craft strong, relatable heroines—like Sinead, who navigates a psycho ex and family drama—sets her apart. Her stories balance humor and heart, with dialogue that pops and scenes that sizzle, earning her comparisons to rom-com queens like Sophie Kinsella.

Why Cassandra O’Leary Matters

Cassandra O’Leary’s impact lies in her ability to bring an Australian perspective to the global romance scene. Her novels celebrate strong, independent women and the messy, beautiful reality of modern love, resonating with readers worldwide. Her debut’s success, including a Czech translation and nominations like the 2016 AusRom Today Reader’s Choice Awards for Best New Author, highlights her growing influence. By championing diversity and authenticity, O’Leary is carving a space for Aussie voices in romantic comedy.

As a mother and former corporate professional, she inspires aspiring writers to chase their dreams, proving it’s never too late to start anew. Her engaging presence at events like the Australian Romance Readers Convention and her active role in writing communities further amplify her influence, making her a beacon for romance fans and writers alike.

About Cassandra O’Leary

  • Born: Dandenong, Victoria, Australia
  • Key Works: Girl on a Plane, Hot in the City, Dating Little Miss Perfect
  • Awards: Winner, We Heart New Talent contest (HarperCollins UK, 2015); Finalist, AusRom Today Reader’s Choice Awards (2016)
  • Fun Fact: O’Leary dreams of food and wine tasting trips to Italy and Spain for “research”!

Ready to fall in love with a hilarious, heartwarming story? Snag Girl on a Plane and dive into Cassandra O’Leary’s irresistible romantic comedies today!

Frequently Asked Questions

Who is Cassandra O’Leary?

Cassandra O’Leary is an Australian romantic comedy author based in Melbourne. Known for her Girl on a Plane series, she won the 2015 We Heart New Talent contest by HarperCollins UK. A former communications pro, she crafts witty, heartfelt stories with a global flair.

What are Cassandra O’Leary’s best books?

Cassandra O’Leary’s top books include Girl on a Plane, a steamy rom-com bestseller, Girl Under the Christmas Tree, a festive novella, Hot in the City, a short story collection, and Dating Little Miss Perfect, a charming indie romance.

What inspired Cassandra O’Leary to write?

Cassandra O’Leary’s love for reading romance novels by authors like Marian Keyes and her own travel adventures inspired her to write. Family anecdotes and her Melbourne life add authenticity to her witty, heartfelt romantic comedies.

What is the <em>Girl on a Plane</em> series about?

The Girl on a Plane series by Cassandra O’Leary follows feisty flight attendant Sinead Kennealy and CEO Gabriel Anderson as they navigate love, travel, and drama across Melbourne, London, and Singapore. It’s steamy, funny, and emotional.

Why is Cassandra O’Leary’s writing unique?

Cassandra O’Leary’s writing blends sharp wit, heartfelt emotion, and vivid settings like Melbourne and Paris. Her strong, relatable heroines and Aussie perspective bring a fresh, authentic voice to romantic comedy.