Series · romance

Crossing the Line

by Tessa Bailey

The Crossing the Line series by Tessa Bailey has 5 books and is best read in publication order, starting with Riskier Business (2015).

Books
5 books
First published
2015
Status
completed
Last checked

Start here: Riskier Business (2015) — then read straight through in publication order.

Cover of Riskier Business, the first book in Crossing the Line

Reading order

The order the books were released — the default way to read the series.

  1. Book 1:

    Riskier Business

    Novel

    Alternative text for cover: Cover of Riskier Business
  2. Book 2:

    Risking It All

    Novel

    Alternative text for cover: Cover of Risking It All
  3. Book 3:

    Up in Smoke

    Novel

    Alternative text for cover: Cover of Up in Smoke
  4. Book 4:

    Boiling Point

    Novel

    Alternative text for cover: Cover of Boiling Point
  5. Book 5:

    Raw Redemption

    Novel

    Alternative text for cover: Cover of Raw Redemption

About the Crossing the Line series

Crossing the Line is a Brooklyn-set romantic suspense series about NYPD detectives working undercover inside organized crime, and the dangerous, high-heat relationships that form across the cop/criminal divide. It opens with Risking It All, in which detective Seraphina Newsom goes undercover to avenge her brother's murder by a mob kingpin, and falls for Bowen Driscol, the reluctant new head of the crime family holding her cover in place. Riskier Business, a 0.5 prequel novella, follows a related couple -- detective Troy and former pool hustler Ruby -- drawn back into one last con. Later books continue the same Brooklyn-underworld world and cast as new couples navigate loyalty, danger, and the law from opposite sides.

Published by Entangled between 2015 and 2016, Crossing the Line is grittier and more plot-driven than much of Bailey's small-town contemporary work, trading banter-forward rom-com for genuine romantic suspense stakes -- undercover identities, mob retaliation, detectives who can't fully trust the people they're falling for. Readers who want Bailey's voice applied to higher-stakes, more plot-heavy suspense rather than her usual small-town or workplace comedy should start here.

How to read this series

Publication order: Riskier Business (a 0.5 prequel novella), then Risking It All, Up in Smoke, Boiling Point, and Raw Redemption. The series follows a connected Brooklyn cast of undercover detectives and the crime family they're entangled with, so while later books can be read as fairly self-contained romantic suspense, starting with Risking It All (or the prequel novella) gives the fullest picture of the world.

Frequently asked questions

How many books are in the Crossing the Line series?

Five: the 0.5 prequel novella Riskier Business, plus Risking It All, Up in Smoke, Boiling Point, and Raw Redemption, published 2015-2016.

What order should I read Crossing the Line in?

Riskier Business (0.5), then Risking It All, Up in Smoke, Boiling Point, Raw Redemption.

Is Crossing the Line a cop romance or a mob romance?

Both -- it's a romantic suspense series about NYPD detectives going undercover inside a Brooklyn organized-crime family, so each couple sits on opposite sides of the law.

Is Crossing the Line connected to Line of Duty?

Not through shared characters -- it's a separate, grittier romantic-suspense world -- though both showcase Bailey's early run of law-enforcement-hero series.

Is Crossing the Line finished?

Yes, all five entries were published in 2015-2016 and the series is complete.


Reading order last verified .