A Court of Thorns and Roses
romantic fantasy
Series · romance
Crossing the Line
The Crossing the Line series by Tessa Bailey has 5 known books (5 published) and is best read in publication order, starting with Riskier Business (2015).
- Books
- 5 known books (5 novels)
- Published
- 5
- First published
- 2015
- Status
- completed
- Shelved under
- Romance
- Last checked
Start here: Riskier Business (2015) — then read straight through in publication order.
Reading order
The date order of published books and any announced future entries — the default way to read the series.
- Book 1:
Riskier Business
Riskier Business , the 0.5 prequel novella, follows detective Troy and former pool hustler Ruby as they're drawn back into one last con, setting up the Brooklyn undercover-cop world the rest of Crossing the Line explores. At 137 pages, it's the shortest entry, published in 2015.
Alternative text for cover: Cover of Riskier Business - Book 2:
Risking It All
Risking It All opens the main series in 2015: 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. It runs 300 pages.
Alternative text for cover: Cover of Risking It All - Book 3:
Up in Smoke
Up in Smoke , the longest entry in Crossing the Line at 328 pages, continues the Brooklyn-underworld world established in Risking It All , pairing a new couple across the same cop/criminal divide. It appeared later in 2015.
Alternative text for cover: Cover of Up in Smoke - Book 4:
Boiling Point
Boiling Point , the third full-length entry, was published in 2015 at 302 pages, keeping to the series' romantic-suspense stakes of undercover identities and mob retaliation within the same Brooklyn cast.
Alternative text for cover: Cover of Boiling Point - Book 5:
Raw Redemption
Raw Redemption closes out Crossing the Line in 2016, the year after the rest of the series, at 240 pages -- the final entry in Tessa Bailey's grittier, plot-driven detour into Brooklyn organized-crime romantic suspense.
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.
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.
If you like the Crossing the Line series
Reading order last verified .