The Recommended Reading Order
If you are looking for a series that combines high-stakes action, absolute absurdity, and sweet, slow-burn MM romance, Alice Winters' The Hitman's Guide series is the perfect escape. The series revolves around the chaotic, flamboyant former hitman Leland (known in the criminal underworld as the Sandman) and Jackson, a straight-laced, by-the-book private investigator who somehow becomes the anchor to Leland's wild antics.
Because the overarching narrative relies heavily on character progression, inside jokes, and the expansion of a tight-knit found family, reading the books in the order they were published is highly recommended. The spin-offs are not optional side stories; they focus on major secondary characters who are integral to the main plot, and the events in those books directly impact the main couple's lives.
Here is the recommended reading path for the entire series:
- The Hitman's Guide to Making Friends and Finding Love (2019)
- The Hitman's Guide to Staying Alive Despite Past Mistakes (2019)
- The Hitman's Guide to Tying the Knot Without Getting Shot (2020)
- The Former Assassin's Guide to Snagging a Reluctant Boyfriend (2021) — Spinoff (Cassel & Jeremy)
- The Hitman's Guide to Righting Wrongs While Causing Mayhem (2022)
- The Hitman's Guide to Codenames and Ill-Gotten Gains (2023)
- The Mercenary's Guide to Mishaps and Romance (2024) — Spinoff (Tavish & Ellis)
- The Hitman's Guide to Stately Fences and Killer Defenses (2026)
The Hitman's Guide Books in Detail
1. The Hitman's Guide to Making Friends and Finding Love (2019)
The book that started it all introduces us to Leland, a flamboyant former contract killer who is trying to live a normal life, and Jackson, a private investigator who is hired to look into him. After Leland accidentally moons Jackson during a stakeout, an unlikely partnership—and a hilarious enemies-to-lovers romance—is born. This book establishes the signature banter, over-the-top action, and chaotic humor that defines the series.
2. The Hitman's Guide to Staying Alive Despite Past Mistakes (2019)
In the second installment, Leland and Jackson's relationship continues to develop as they deal with threats stemming from Leland's past as the Sandman. This book is particularly notable for introducing Cassel, a former hitman protégé of Leland's late mentor who takes a job as their eccentric housekeeper. Cassel immediately becomes a fan-favorite character with his deadpan delivery and strange habits.
3. The Hitman's Guide to Tying the Knot Without Getting Shot (2020)
Leland and Jackson are planning their wedding, but in their world, things are never simple. As they navigate caterers and floral arrangements, they must also dodge assassins and deal with family drama. This book brings the initial trilogy of Leland and Jackson's romance to a satisfying, action-packed milestone.
4. The Former Assassin's Guide to Snagging a Reluctant Boyfriend (2021)
This is the first official spin-off and shifts the perspective to Cassel. Now working as a private investigator, Cassel sets his sights on Jeremy, a straight-laced police officer who previously saved his life. While Leland and Jackson are relegated to supporting roles, their chaotic energy is still felt as they try to help Cassel win Jeremy over. This book is essential to read before moving on, as it sets up Cassel and Jeremy's relationship for future installments.
5. The Hitman's Guide to Righting Wrongs While Causing Mayhem (2022)
Returning to Leland and Jackson as the main POV characters, this book dives deeper into Leland's past. The crew is forced to go on a rescue mission that tests their abilities and brings their found family even closer together. The humor remains as absurd as ever, featuring disco ball piñatas, aerial silks, and ridiculous disguises.
6. The Hitman's Guide to Codenames and Ill-Gotten Gains (2023)
Leland and Jackson face new mysteries and dangerous criminals while navigating their domestic life. The found family dynamic is on full display here, with Cassel, Jeremy, and the rest of the crew getting dragged into Leland's elaborate and chaotic schemes.
7. The Mercenary's Guide to Mishaps and Romance (2024)
The second spin-off shifts the spotlight to Tavish, a charismatic mercenary who has frequently aided the main crew. Tavish finds himself in a forced-proximity situation with Ellis, a completely normal vet tech who gets caught up in the criminal underworld due to a massive misunderstanding. The main crew appears in supporting roles to help Tavish rescue Ellis and navigate his feelings.
8. The Hitman's Guide to Stately Fences and Killer Defenses (2026)
The eighth installment returns the focus to Leland and Jackson. The couple is attempting to enjoy a normal domestic life with their son, Waylon. However, the peace is shattered when someone from Leland's past places a massive bounty on his head. Leland and his found family must band together to neutralize the threat once and for all.
Chronological vs. Publication Order & Reading Caveats
For some series, chronological order differs from publication order due to prequels. However, for The Hitman's Guide, the chronological timeline flows exactly in the order the books were published. Because each book references the events of the previous ones, attempting to skip the spin-offs (Books 4 and 7) will lead to confusion. For example, Cassel and Jeremy's relationship in Book 5 will seem abrupt if you skip Book 4, and Tavish's character development in Book 8 builds directly on the events of Book 7.
What to Know Before You Start
Alice Winters' writing style is fast-paced, dialogue-heavy, and relies heavily on absurd comedy. Leland is an incredibly chaotic protagonist who talks constantly, makes inappropriate jokes, and deliberately exasperates the serious Jackson. If you prefer grounded, realistic romantic suspense, this series might feel too over-the-top. However, if you enjoy found family dynamics, hilarious banter, and characters who would burn the world down for each other, it is a must-read.