Meet the Author Monday: Cassandra O’Leary

Cassandra O'Leary

It’s Meet the Author Monday! Each week we meet a new author and get to know a little about them, their writing process, publishing experience, and tips for other writers. Today we’re talking to Cassandra O’Leary, author of Dating Little Miss Perfect.

About Cassandra O’Leary:

Cassandra O’Leary is an Aussie romance, romantic comedy and women’s fiction author, corporate communications escapee, avid reader, and film and TV fangirl.

In 2015, Cassandra won the global We Heart New Talent contest run by HarperCollins UK and her debut novel, Girl on a Plane, was released in 2016 (re-released in a new edition in 2023). Cassandra was also a finalist in contests run by AusRom Today, Romance Writers of America and Romance Writers of Australia. She has indie published several titles including a romcom story collection, Hot In The City and a romcom novel, Dating Little Miss Perfect.

You’ll find Cassandra in Melbourne, Australia, chasing her two high-energy mini ninjas and drinking excellent coffee with her superhero husband.

Cassandra O’Leary is a proud member of Romance Writers of Australia, the Australian Society of Authors, and the Melbourne Romance Writers Guild. Read more at

About Dating Little Miss Perfect:

The perfect romcom read for fans of The Soulmate Equation by Christina Lauren and The Hating Game by Sally Thorne . . .

The Accidental Housemate

On an anonymous online dating app, LittleMissPerfect meets HotAussie007 and it’s love at first click. In real life, a smart but spiky woman in STEM, research scientist, Dr Eden, meets a laid-back Aussie marketing manager, Finn, at the big pharma company where they both work in California. They’re forced to compete for special project funding, and both their jobs are on the line.

Eden just wants to win at science and in life. It’s not happening! She can’t stand Finn’s too-cool-for-school, nice guy act, or his delectable forearms that keep invading her space. While Finn is stupidly attracted to Eden, when she’s not telling him off, he isn’t free to pursue her. He’s stuck in the worst position in his professional life, and doesn’t see a clear way out. He can’t tell her the whole truth about what’s going on at work or in his personal life. . . or it could all blow up in his face.

When they realise the truth about their online alter egos, dating is off the table. Can they ignore their inconvenient attraction, and work together to take down their unethical boss? Or will intense rivalry cause their IRL work lives and online love lives to collide and explode like a science experiment gone wrong?

Author Interview with Cassandra O’Leary:

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  1. Does writing energize or exhaust you?

  Both! I find the initial phase of finding out about a story and chasing new ideas to be exciting and energising, but as the process drags on…and on…through multiple edits, it can be exhausting. Writing Dating Little Miss Perfect became exhausting in the final slog of edits, when it became known as The Story That Will Never End. When it finally did end, I was as shocked as anyone! This book took about six years to write, on and off, in between other projects. It morphed from a short romance to a long, single title novel.

  1. Did you ever consider writing under a pseudonym?

  Yes, but I’m currently writing under my own name. I think my name suits the contemporary romance and romcom genres but I would certainly choose a different name if I go ahead and write something completely separate, like sci fi, cosy mystery or fantasy. I’ve toyed with a few other genres, so this is a real possibility. An author name needs to fit with brand and genre expectations. I do roll my eyes at people in my ‘real life’ who ask me how I can publish romance under my real name or tease me about writing steamy scenes. If it’s not for you, just don’t read it, friends!

  1. Do you try more to be original or to deliver to readers what they want?

  It’s a combination, for me. The romance genre has a promise to readers, to deliver the happily ever after (or at least a happy for now ending) and I would not try to do something different if it meant upsetting or disappointing those readers. I went to a writing workshop once and the presenter suggested readers often want “same, same, but different” and I think that’s right. Readers may choose a certain type of book for the experience they expect, but if there are a few surprises thrown in, that makes it even better. 

  1. What other authors are you friends with, and how do they help you become a better writer?

  I have some good writer friends within the Romance Writers of Australia community and my local writing group, the Melbourne Romance Writers Guild. Not all of them write in the same sub-genres as me, for example Michelle Somers (romantic suspense/paranormal romance), Savannah Blaize (paranormal romance), Samara Parish (historical romance) but I also connect with writers in my sub-genres online. My closest writer friends will let me use them as a sounding board for my sometimes wacky ideas, read scenes or drafts and provide feedback, or suggest things I might not have thought of – such as backstory ideas or ways of working or marketing.    One friend talked to me about letting a draft sit and percolate for a while before editing. Someone else suggested interviewing the characters as if I was a journalist, when I get stuck. Another said she was bad at marketing, but she’s actually awesome at face-to-face networking and PR and I could learn from her, since I usually focus on social media. It all makes me think and helps me improve as a writer. I also love to read other authors’ books across many genres. 

  1. How many unpublished and half-finished books do you have?

  Currently, I’m working on a romcom novella and also have two partial romance novels in the drawer (plus my first attempt at a novel that won’t see the light of day, and another draft in a different sub-genre that’s probably terrible). I also have notes for about three other books that I’m considering writing, but time will tell if I get more ideas to help develop them. I’m not a fast writer, unfortunately, so I have to let some stories spin around in the back of my mind for quite a while before I’m ready to focus on them. 

  1. How do you select the names of your characters?

  So far, I’ve used baby name websites and looked at the meanings behind names, chosen names that fit with the character’s ethnic background, and randomly used names I heard in the past e.g., a kid in my child’s kindergarten many years ago. Eden from Dating Little Miss Perfect was named for a soap opera character from the old series, Santa Barbara! It just popped into my head. I wanted her to have a soft, feminine name while working in a male-dominated industry. 

  1. Is writing your full-time career? Or would you like it to be?

  I consider myself a part-time writer at the moment. I have chronic illnesses and two kids, a teen and a tween, which all conspire to make me tired and eat up my time. I would definitely like to earn enough money from writing for it to be my full-time gig. But I can’t imagine sitting at a desk for a solid eight or nine hours to write these days. 

  1. What were the key challenges you faced when writing this book?

  I made the plot quite complicated for a romcom. I have a habit of doing this to myself! As I am a pantser or organic writer, I don’t have the plot nailed down before I start to write. I have to work it out as I go along, and that includes any sub-plots with a hint of mystery. I had to go away and think about the boss and his ulterior motives for a long time when writing Dating Little Miss Perfect. I wrote another novella in the meantime. Finally, something clicked and I woke one morning with the idea for what the nasty man was up to. I won’t mention it here because *spoilers* but once I had that key piece worked out, I could write through to The End. 

  1. What famous author do you wish would be your mentor?

  I would love Marian Keyes to be my mentor. Even if she only wanted to tell jokes and talk about nail varnishes, it would be the most wonderful thing. If I could absorb her brilliance by osmosis, I would!

To learn more about Cassandra O’Leary, here’s where you can find her:

Twitter: @cass_oleary

Meet the Author Book Promotion

Published by Kelly Schuknecht

Kelly Schuknecht is a marketer with a background in the publishing industry. She is passionate about all things related to books and loves helping authors navigate the world of social media for book promotion. She recently launched the course Marketing Your Book on TikTok.

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