
A Vine Mess
romance
Series · romance
The Crossing the Line series by Tessa Bailey has 5 books and is best read in publication order, starting with Riskier Business (2015).
Start here: Riskier Business (2015) — then read straight through in publication order.
The order the books were released — the default way to read the 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.
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.
Five: the 0.5 prequel novella Riskier Business, plus Risking It All, Up in Smoke, Boiling Point, and Raw Redemption, published 2015-2016.
Riskier Business (0.5), then Risking It All, Up in Smoke, Boiling Point, Raw Redemption.
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.
Not through shared characters -- it's a separate, grittier romantic-suspense world -- though both showcase Bailey's early run of law-enforcement-hero series.
Yes, all five entries were published in 2015-2016 and the series is complete.
Reading order last verified .