Where to Start: The Perfect Seattle Entry Point
If you want to experience Kristen Proby's sprawling contemporary romance universe the way it was intended, you should start at the very beginning with Come Away with Me. This debut novel introduces photographer Natalie Conner and Hollywood star Luke Williams, setting the stage for the tight-knit family dynamics, cozy coffee shop vibes, and steamy romance that define the series. Starting here allows you to meet the core Montgomery clan and understand their deep bonds before the family tree expands into various spinoffs and subseries.
While every book is written as a standalone romance focusing on a single couple's happy-ever-after, the recurring appearances, family dinners, and group chats make reading them in order highly rewarding. If you jump in mid-series, you will still enjoy the individual romance, but you might find yourself slightly spoiled on the relationships of characters who fell in love in earlier installments.
Publication Order of With Me In Seattle Books
Following the publication order is the cleanest way to watch the Montgomery family grow and branch out into new circles of friends, colleagues, and neighbors in the Seattle area:
- Come Away with Me (2012) – Focuses on Natalie Conner and Luke Williams as they navigate instant chemistry and Hollywood privacy issues.
- Under the Mistletoe with Me (2012) – A festive holiday novella featuring Isaac Montgomery and Stacy Stone.
- Fight with Me (2012) – An office romance starring Jules Montgomery and her boss, Nate McKenna.
- Play with Me (2013) – Follows professional football player Will Montgomery and pediatric nurse Meg.
- Rock with Me (2013) – Dives into the music scene with rock star Leo Nash and Samantha Williams.
- Safe with Me (2013) – Caleb Montgomery and Brynna Allen find love amidst past trauma.
- Tied with Me (2014) – Follows protective detective Matt Montgomery and independent bakery owner Nic Dalton.
- Breathe with Me (2014) – A heartwarming second-chance romance with Mark Williams and Meredith.
- Forever with Me (2014) – The final book in the initial Montgomery family arc, focusing on Dominic Salvatore and event planner Alecia.
- Easy with You (2015) – A crossover novella featuring Asher Smith and Lila Bailey, bridging the Seattle universe with New Orleans.
- Burn with Me (2018) – A standalone novella focusing on Bailey (previously published as Playing with Fire in 2014).
- Stay with Me (2018) – Launches the Crawford family focus with Amelia "Leah" Montgomery and architect Wyatt Crawford.
- Indulge With Me (2018) – A special anthology featuring recipes, celebrations, and check-ins with established series couples.
- Love with Me (2018) – A friends-to-lovers story featuring cardiothoracic surgeon Jace Crawford and veterinarian Joy Thompson.
- Dance with Me (2019) – Features pop superstar Starla and police officer Levi Crawford.
- Wonder With Me (2019) – A holiday romance starring Reed Taylor and interior designer Noel Thompson.
- Dream with Me (2020) – Kane O’Callaghan, a glass artist, and cake designer Anastasia Montgomery find a spark.
- You Belong with Me (2020) – A second-chance romance featuring Archer Montgomery and Elena Watkins, introducing minor mafia-related suspense elements.
- Imagine with Me (2020) – Screenwriter Shawn O’Callaghan and shy author Lexi Perry adapt her book for the screen.
- Shine with Me (2020) – Fitness trainer Benjamin Demarco helps former actress Sabrina Harrison prepare for the role of a lifetime.
- Escape With Me (2021) – Runaway bride Izzy Harris stumbles into Keegan O’Callaghan's island pub.
- Flirt With Me (2021) – Real estate agent Maeve O’Callaghan meets single father Hunter Meyers.
- Change With Me (2021) – An accidental-roommates romance between Hollywood star Zane Cooper and teacher Aubrey Stansfield.
- Take A Chance With Me (2022) – Maggie O’Callaghan and former military hacker Cameron Cox wrap up the O'Callaghan sibling arc.
Interconnected Families and Subseries
As the series progressed, Proby organized the novels into distinct subseries focusing on specific groups of siblings and friends, though they all exist in the same continuity and are heavily interconnected:
The Montgomery Family Saga
The first eight books (from Come Away with Me through Forever with Me, along with the holiday novellas) form the core Montgomery family arc. These books focus on the original siblings and close friends who established the series' cozy, family-first tone.
The Crawford Family Spin-off
Beginning with Stay with Me, the focus shifts slightly to the Crawford family (Wyatt, Jace, and Levi) and their partners. These books maintain the Seattle setting and feature frequent cameos from the original Montgomery couples, serving as a natural extension of the universe.
The O'Callaghan Family Spin-off
Starting with Dream with Me, readers are introduced to the large, welcoming Irish O'Callaghan family (Kane, Shawn, Keegan, Maeve, and Maggie). Set on a small island just outside of Seattle, this subseries introduces pub life, local real estate, and glass artistry while keeping the signature Proby warmth.
Chronological Reading Caveats and Standalone Guide
While publication order is the most logical path, readers do not need to stress about strict ordering. Because each book wraps up its primary romantic conflict with a satisfying resolution, you can easily pick up a subseries (like the O'Callaghans) or a single book (like the holiday novellas) without feeling lost. The main caveat to keep in mind is the rapid passage of time across the series: children grow up in the background, couples marry, and families expand. If you read the books out of order, you will see characters happily married before you read the story of how they met.
Spinoffs and Crossover Connections
For readers who cannot get enough of the Pacific Northwest, Kristen Proby has expanded this world even further with distinct spinoff lines:
With Me in Seattle: Mafia
For a darker, higher-stakes romance experience, Proby wrote the Martinelli Mafia trilogy (Underboss, Headhunter, and Off the Record, all published in 2021). While set in the same Seattle environment, these books should be read in their own sequential order as they follow a continuous plot involving the Martinelli crime family.
Single in Seattle: The Next Generation
If you want to see what happens to the children of the original couples once they grow up, the Single in Seattle series (beginning with The Secret) focuses on the adult lives and romances of the next generation of Montgomerys, such as Caleb and Brynna's children, Drew and Maddie.
The Boudreaux Crossover
The novella Easy with You serves as a direct bridge between the Seattle universe and Proby's New Orleans-based Boudreaux series. It features Asher Smith (Matt Montgomery's detective partner) and Lila Bailey (best friend to the Boudreaux family), making it the perfect crossover read.