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Chaotic Romance Reader

And We Read Happily Ever After

Review: How to Fail at Flirting by Denise Williams

July 27, 2025

How to Fail at Flirting incorporates heavy topics while still bringing the romance to the story. Well paced, complex characters, and good writing make this a great read.

Genre: Contemporary Romance

Steam: Explicit

Publisher: Berkley Romance

Pub Date: December 01, 2020

Available: Amazon | Barnes & Noble | BookShop


How to Fail at Flirting Synopsis

One daring to-do list and a crash course in flirtation turn a Type A overachiever’s world upside down.

When her flailing department lands on the university’s chopping block, Professor Naya Turner’s friends convince her to shed her frumpy cardigan for an evening on the town. For one night her focus will stray from her demanding job and she’ll tackle a new kind of to-do list. When she meets a charming stranger in town on business, he presents the perfect opportunity to check off the items on her list. Let the guy buy her a drink. Check. Try something new. Check. A no-strings-attached hookup. Check…almost.

Jake makes her laugh and challenges Naya to rebuild her confidence, which was left toppled by her abusive ex-boyfriend. Soon she’s flirting with the chance at a more serious romantic relationship—except nothing can be that easy. The complicated strings around her dating Jake might destroy her career.

Naya has two options. She can protect her professional reputation and return to her old life or she can flirt with the unknown and stay with the person who makes her feel like she’s finally living again.

TW: Domestic Abuse is a large part of this novel and is often graphic and descriptive at times.


Review:

How to Fail at Flirting is good. Like really, really good. Like please pick this up and read it good! Naya is everything I could ever want in a lead and so is Jake. They’re a stunning couple. Naya is a survivor of domestic abuse and watching her confront everything is awe-inspiring. I wanted to give her a hug so many freaking times. Jake’s patience, communication, and understanding win him a special place in my heart for male leads. The amount of communication and talking through the big, real things was phenomenal. Can all books have this? The plot of long-distance relationship, the mix of their jobs, and the realness of both characters sold me.

Williams’ writing is easy to read and the way that she interweaves the difficult details into the novel, amping up the tension with each turn is beautiful. The ending isn’t quickly brushed off, rather the characters have to confront each other and deal with the aftermath. I appreciated that Williams went there with her characters. Thank you.

Long Story Short

Do I recommend this book? Yes!! As long as you know the content warnings before going into this and are able to read it, then yes. I loved this book so much and really enjoyed the entire novel.


If You Liked This One I Recommend…

I would highly recommend checking out Beach Read by Emily Henry. This book tackles issues of writers block, second chance romance, grief, death cults, and family secrets. I also would recommend any of Denise Williams’ other books like Fastest Way to Fall, Do You Take This Man, and Technically Yours. From a historical romance side I would recommend The Hellion and the Hero by Emily Sullivan– very VERY similar vibes.

in Book Reviews, Contemporary Romance, Recommend # Diverse Reads, STEM Romance

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