How to Fail at Flirting: A Complete Reader's Guide

Name: How to Fail at Flirting
Author: Denise Williams

⚠️ Spoiler Warning: This guide contains detailed spoilers for the entire novel. Proceed only if you've finished reading or are comfortable knowing the plot.

Quick Facts

Item	Detail
Author	Denise Williams
Published	2020
Genre	Contemporary romance
Setting	University campus in Chicago; also Cincinnati and North Carolina
Narrator	Naya Turner (first‑person)

Short Summary

Naya Turner, a math‑education professor, faces tenure review while recovering from an abusive past relationship. When a chance encounter with consultant Jake Shaw turns into a secret affair, her carefully controlled life unravels. Professional conflicts, the return of her abusive ex‑boyfriend Davis, and the threat of department cuts force Naya to confront her trauma head‑on. Through self‑defense, therapy, and the support of friends, she learns to trust again and fight for both her career and the love she deserves.

Full Summary

Naya Turner is a math‑education professor whose world shrinks to her office and her to‑do lists. Her department chair warns that the education program may be cut, and worse, her abusive ex‑boyfriend Davis Garner is back on campus. Flashbacks reveal how Davis controlled Naya’s appearance and emotions, once even twisting her arm into a podium after accusing her of flirting.

At dinner with best friends Felicia and Aaron, Naya is teased about her lack of a sex life. They create a playful list of goals that includes flirting and sex with a stranger. Naya reluctantly agrees to go to a bar—and meets Jake, a charming out‑of‑town consultant. Despite a disastrous first date that ends with her vomiting in his hotel bathroom, Jake asks her out again. Naya uses the alias “Michelle” but eventually admits her real name.

Their romance deepens over a Ferris‑wheel date, mutual confessions, and fully consensual sexual encounters. Jake becomes the first partner to give Naya an orgasm. But at a university reception, Naya is horrified to discover that Jake is the consultant hired to restructure her department—and that he owns the firm. After a tense conversation, they agree to a brief, secret affair.

The affair continues despite professional risk. Naya’s friends Felicia and Aaron offer support, and she starts to open up. However, her ex Davis resurfaces, sending anonymous texts threatening to leak nude photos and sabotage her tenure. Jake learns about the abuse but doesn’t know Davis is on the tenure committee.

When Jake’s consulting team recommends cuts to the education department, Naya panics. A misunderstanding leads to a painful breakup. Meanwhile, at a committee retreat, Davis corners Naya, taunts her, and becomes physically violent. Using self‑defense she learned in kickboxing class, Naya fights him off. Colleagues witness the assault, and Jill validates Naya’s story.

In the aftermath, Naya seeks counseling, begins healing, and reconnects with Jake. They reconcile, and she admits she loves him. The epilogue shows Naya earning tenure, buying a house with Jake, and expanding her friend group. Davis faces legal consequences but serves no jail time. The novel ends with Jake promising everyday commitment.

Main Characters

Naya Turner – A math‑education professor navigating tenure, trauma recovery, and a secret romance.
Jake Shaw – A high‑profile consultant who falls for Naya and supports her healing.
Davis Garner – Naya’s abusive ex‑boyfriend who threatens her career and safety.
Felicia – Naya’s loyal, outspoken friend who encourages her to take risks.
Aaron – Naya’s colleague and friend who challenges her to stop pushing people away.
Jill – A colleague who witnesses Davis’s harassment and becomes part of Naya’s support network.

Themes

Trauma recovery – Naya moves from silencing her abuse to seeking counseling and using self‑defense.
Trust and vulnerability – She gradually opens up to Jake and her friends despite deep‑seated fears.
Power dynamics in academia – Tenure, department cuts, and conflicts of interest shape Naya’s choices.
Self‑advocacy – Her to‑do list evolves into a tool for reclaiming agency.
Consent and communication – The romance emphasizes enthusiastic consent and honest disclosure.

Symbols

To‑do list – Begins as a sex‑friendly checklist and becomes a guide for reclaiming her life.
Cardigan – Represents Naya’s professional armor; she sheds it to embrace risk.
Ferris wheel – A setting for vulnerable confessions, symbolizing the highs and lows of the relationship.
Self‑defense class – Kickboxing represents her physical and emotional empowerment.

Ending Overview

In the epilogue, Naya has earned tenure, bought a house with Jake, and expanded her circle of friends. Davis is convicted but serves no jail time. Naya and Jake attend a wedding together, and Jake hints at proposing by mentioning cake tasting. The novel ends with a promise of everyday commitment. For a deeper analysis, visit the ending explained page.

Common Questions

What is Naya Turner’s job? She is a math‑education professor at a Chicago university facing tenure review.
Who is Davis Garner? He is Naya’s abusive ex‑boyfriend who returns to campus and threatens her career.
Does Naya end up with Jake? Yes. After reconciling and healing, they build a life together.
Does Naya get tenure? Yes. In the epilogue, she has earned tenure.
What is the to‑do list? A playful list created by Naya’s friends that evolves into her own tool for self‑advocacy and risk‑taking.
Why does Naya use the name “Michelle”? She gives a fake name during her first meeting with Jake out of caution and fear.
Is Jake married? He was married to Gretchen but had been legally separated for over a year when he meets Naya.
What happens to Davis? He is charged for the assault but serves no jail time, as noted in the epilogue.

Chapter-by-Chapter Breakdown

Ch.	Title	Summary
1	Chapter One	Naya learns her department may be cut and that her abusive ex Davis is back on campus.
2	Chapter Two	At dinner with friends, Naya is encouraged to take risks; a to‑do list is created.
3	Chapter Three	Naya meets Jake at a bar; they go for ice cream and she uses a false name.
4	Chapter Four	A date at the Hancock Building ends with Naya vomiting in Jake’s hotel room.
5	Chapter Five	Jake texts Naya and asks her out again; she agrees despite embarrassment.
6	Chapter Six	Naya gets date advice from Felicia and picks out matching lingerie.
7	Chapter Seven	A Latin dance lesson triggers Naya’s trauma; Jake patiently guides her.
8	Chapter Eight	On the Ferris wheel, they exchange vulnerable secrets and share a passionate kiss.
9	Chapter Nine	A fully sober sexual encounter deepens their emotional bond.
10	Chapter Ten	On campus, a colleague mentions Davis’s name, triggering Naya’s anxiety.
11	Chapter Eleven	At a university reception, Naya is alarmed to see the consulting partner—likely Jake.
12	Chapter Twelve	Naya discovers Jake is the consultant; they agree to talk privately.
13	Chapter Thirteen	Naya invites Jake to her apartment to end things but they begin a secret affair.
14	Chapter Fourteen	Their first sexual encounter emphasizes consent; Naya reveals her multiracial background.
15	Chapter Fifteen	Morning after panic; Jake offers nicknames and promises to check with HR.
16	Chapter Sixteen	Naya sees Davis on campus and receives threatening texts from an unknown number.
17	Chapter Seventeen	Naya confides in Felicia about the affair and worries about career risk.
18	Chapter Eighteen	Sexting deepens Naya’s trust and desire.
19	Chapter Nineteen	Naya overhears a woman claim to be Jake’s wife.
20	Chapter Twenty	Naya flees the hotel; Jake asks to explain his separation.
21	Chapter Twenty-one	Jake explains his marriage is over; Naya chooses vulnerability.
22	Chapter Twenty-two	Naya spends their last hours together before Jake’s flight.
23	Chapter Twenty-three	Davis sends Naya a nude photo and threatens to ruin her tenure.
24	Chapter Twenty-four	First official date; Jake confirms their relationship isn’t a formal violation.
25	Chapter Twenty-five	Jake gives Naya custom pencils; they plan a weekend in Cincinnati.
26	Chapter Twenty-six	Naya is sick in Cincinnati; Jake cares for her without expectations.
27	Chapter Twenty-seven	Naya starts self‑defense classes; she accepts Jake’s gala invitation.
28	Chapter Twenty-eight	Naya learns Davis may be hired; she researches him and feels panicked.
29	Chapter Twenty-nine	At the gala, Naya faces racism from a donor and later leaves with Jake.
30	Chapter Thirty	Naya visits Jake’s home; they agree to be exclusive.
31	Chapter Thirty-one	Jake’s ex‑wife confronts them at brunch; Jake introduces Naya as his girlfriend.
32	Chapter Thirty-two	Jake reveals his marriage lacked passion; Naya learns Joe had a heart attack.
33	Chapter Thirty-three	Davis arrives at a committee meeting; Naya freezes and fails to speak up.
34	Chapter Thirty-four	Davis sends threatening texts; Felicia urges Naya to tell Jake.
35	Chapter Thirty-five	Naya tells Jake about the abuse but hides Davis’s role on the tenure committee.
36	Chapter Thirty-six	Jake reveals cuts to her department and that his team disclosed their relationship.
37	Chapter Thirty-seven	Naya avoids Jake; Aaron confronts her pattern of pushing people away.
38	Chapter Thirty-eight	Naya prepares for a retreat; Felicia sees she is not okay.
39	Chapter Thirty-nine	Davis corners Naya at the retreat; Jake witnesses but turns away.
40	Chapter Forty	Naya publicly confronts Davis; President Lewis offers support.
41	Chapter Forty-one	Davis attacks Naya; she uses self‑defense and others intervene.
42	Chapter Forty-two	Naya gives a police statement; she and Jake reconcile.
43	Chapter Forty-three	Four weeks later, Naya starts counseling and a former student inspires her.
44	Chapter Forty-four	The university retreat evaluates departments; Naya’s is safe.
45	Chapter Forty-five	Naya and Jake reconcile by the lake; they confess their love.
46	Epilogue	Naya earns tenure, buys a house with Jake, and they attend a wedding.
47	Author’s Note	The author provides the National Domestic Violence Hotline.
48	Excerpt	Promotional preview of The Fastest Way to Fall.