Audiobook Review: How to Fail at Flirting

Author: Denise Williams

Narrator: January LaVoy

Audiobook Length: 9 hours 6 minutes

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.

The title of this novel, How to Fail at Flirting, seems to be a misnomer as there is barely any flirting in this novel. There are multiple times the main characters keeps having an inner monologue about how bad she is at flirting, but she actively flirted and failed for about five seconds and then there is nothing else really mentioned about it. I think I entered this novel not in the right headspace for this type of story as I expected one thing and was delivered another. There are darker themes as the character deals with her abusive ex as the synopsis states, but it seemed to be the main topic for the character compared to the cuter romance story that the cover and rest of the synopsis suggests. The actual novel itself is not bad, but it is nothing like I thought it would be and it made me more nitpicky than I usually would be for a novel of this type.

Naya is a 33-year-old math education professor in Chicago (honestly had no idea that this super specific profession existed, so I learned something new). She is on her final year before being eligible for tenure – this is another place the book lost me. Naya went to obtain her undergrad out of state at 18 and says it takes ~7 years after starting to get tenure. This means she did everything in her undergrad and grad school in eight years. Granted you can skip the Masters and go straight into PhD, so I will assume the character did that. An undergrad without any issues and being a full time student takes four years so that now leaves four years to go with grad school. I know it is a minor detail as nothing in novels needs to make sense, but, to me, it just set the stage for how unrealistic this novel would be.

Her friends convince her to go out one night to try a list of flirting techniques. She tries for five seconds with the bartender and fails. While on the phone with her friend, she intrigues the attention of the guy sitting next to her and they immediately hit it off and go on a whirlwind first date. I loved that Chicago’s TILT was featured and highly recommend that every single person give this a try if they are ever in the area! [TILT in Chicago]  Their first date does not end in the best way, so, initially, Naya believes it was a bust. However, Jake surprises her by contacting her and the two of them get to know each other. Their relationship was really cute and filled with tons of chemistry. As a pet peeve, Naya describes Jake as a nerd, but he is not and is a dweeb as he does not fit into the standard definition at any point for obsession on a subject. [Here is a handy Venn Diagram to illustrate the standard definitions] This did not negatively affect my thoughts, but just something that came to mind when I was speaking about this novel with my friends.  As a couple, Jake and Naya would really well together in the long run, so they were an easy couple to root for and Jake is an extremely good support system.

Naya has a complicated past with relationships as her last boyfriend, who worked with her at the university at one time, was abusive (physical and emotional). He left for a year to take another job, but when he reenters the pictures, Naya’s life becomes more complicated as every traumatic emotion she experienced comes back to the surface. When Davis comes back in her life, he texts her right after seeing her and it made me question the logistics of how he did that. Naya changed her number after breaking up, so it made me curious how he was able to accomplish this when it is known the two of them broke up. It was a very well-done way to illustrate that out of sight does not always equal out of mind as Naya may be able to temporarily distract herself, but she never truly forgot everything that happened to her.

The novel given is an amazing journey about Naya having a traumatic past, getting a temporary break from it after Davis goes away, she gets her dating groove back, but then everything comes crashing down after Davis reenters the picture. There is additional drama with Naya’s job, but I felt myself more drawn to Naya’s emotional journey. She makes mistakes and sometimes came across as naïve, but that made her very relatable as it seemed very realistically written. Jake was honestly perfect, so, although he is not my ideal love interest, as I prefer some push and pull, he was an ideal addition for Naya. Although this story was not for me, I can easily see how others can read/listen to it and find it to be close to (if not an actual) 5-star read. I would still read any and all other novels by Denise Williams, as I found her writing to be easy to read and her characters to be done well. I may circle back to it one day, but sometimes a book just does not work for a reader and this just happened to be one of them.