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New York Billionaires Books in Order

6 Books
2021 – 2022 Published
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Reading order

The Recommended Reading Order

The New York Billionaires series by Olivia Hayle consists of five standalone contemporary romance novels and one holiday follow-up novella. Because each story focuses on a different couple, you can read them as standalone romances. However, the characters are closely connected, and later books frequently feature spoilers, cameos, and updates on the couples from earlier books. To get the best reading experience, it is highly recommended to read them in their official publication order.

  1. Think Outside the Boss (Published June 7, 2021) – Features Tristan and Freddie.
  2. Saved by the Boss (Published July 22, 2021) – Features Anthony and Summer.
  3. Say Yes to the Boss (Published October 8, 2021) – Features Victor and Cecilia.
  4. A Ticking Time Boss (Published February 11, 2022) – Features Carter and Audrey.
  5. Suite on the Boss (Published October 28, 2022) – Features Isaac and Sophia.
  6. 12 Days of Bossmas (Published December 1, 2022) – A holiday sequel novella featuring all five couples.

What to Know Before You Start

Olivia Hayle's books are known for avoiding the overly dark, toxic billionaire tropes in favor of witty banter, mutual respect, and high-heat chemistry. The New York setting isn't just a background detail; it shapes the fast-paced, high-stakes lives of these characters, from corporate offices to Manhattan holiday events.

While the first five books can technically be enjoyed in any order, 12 Days of Bossmas should absolutely be saved for last. This holiday novella is set two years after the events of the main series and brings all five couples back together for a shared getaway, serving as an extended epilogue for the entire franchise.

The Books in Detail

1. Think Outside the Boss (2021)

The series kicks off with a classic accidental-boss romance. Freddie has a passionate, anonymous one-night stand with a handsome stranger, only to discover the next morning that he is Tristan Thorne, the demanding new CEO of her firm. The story establishes the series' signature mix of workplace tension and playful banter.

2. Saved by the Boss (2021)

The second installment follows Anthony Winter, a cynical, closed-off billionaire, and Summer, an optimistic matchmaker. When Summer is hired to find a partner for Anthony, a bet between the two leads to a fake relationship that quickly blurs the lines between business and real emotion.

3. Say Yes to the Boss (2021)

This novel centers on a marriage of convenience. Cecilia is stuck in a difficult spot when her devilish boss, Victor St. Clair, proposes a mutually beneficial temporary marriage. The close proximity forces both to confront their growing, unspoken feelings.

4. A Ticking Time Boss (2022)

Audrey Ford meets Carter Kingsley when he steps in to rescue her from a disastrous blind date by pretending to be her companion. They exchange numbers and strike up a sweet connection over text messages. However, Carter is secretly a corporate raider whose firm has just targeted the newspaper where Audrey works, setting up a clash between personal trust and professional survival.

5. Suite on the Boss (2022)

Sophia plans a fake-dating scheme with CEO Isaac Winter (brother to Anthony Winter from the second book) to get revenge on her cheating ex. Isaac agrees to the arrangement for his own corporate image, but the faux relationship turns real as the two share close quarters.

6. 12 Days of Bossmas (2022)

A festive novella that wraps up the series. Set two years after the end of the novels, it follows all five couples during a snowy cabin getaway. It provides fans with updates on how their favorite characters are doing and delivers a satisfying final dose of romance.

Spin-offs and Connected Universes

While the New York Billionaires series has reached its natural conclusion with 12 Days of Bossmas, Olivia Hayle has authored other standalone billionaire romance series, such as the Seattle Billionaires series (beginning with Billion Dollar Enemy) and the Brothers of Paradise series. While they share similar themes and a wealthy contemporary setting, they take place in different cities and do not require reading the New York books first.

Frequently Asked

QCan the New York Billionaires books be read as standalones?

Yes, the first five novels are standalone romances focusing on different couples and can be read out of order. However, reading them in publication order is recommended to avoid minor spoilers, as characters from previous books make frequent cameos.

QWhat is the recommended starting point for the series?

You should start with Think Outside the Boss, which is the first book in the series and introduces Olivia Hayle's signature workplace romance style and New York setting.

QWhen should I read 12 Days of Bossmas?

You should read 12 Days of Bossmas last. It is a holiday reunion novella set two years after the events of the main books and features updates on all five couples, acting as a series epilogue.

QAre any of the billionaires related?

Yes. Anthony Winter, the hero of the second book Saved by the Boss, is the brother of Isaac Winter, the hero of the fifth book Suite on the Boss.

QIs there a chronological reading order that differs from publication order?

No. The chronological order matches the publication order exactly, ending with the holiday novella 12 Days of Bossmas.