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The Baileys Books in Order

Part ofPiper Rayne Books in Order

Explore The Baileys books by Piper Rayne in order, with summaries, family connections, series background, and where to begin in Lake Starlight.

Last updated: June 29, 2026

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The Baileys books in publication order

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12 books

1

Advice from a Jilted Bride

by Piper Rayne

2019

After being dumped by text on her wedding day, a heroine starts rebuilding with help from the hot neighbor she accidentally injures. Then she learns he is also her boss.

2

Birth of a Baby Daddy

by Piper Rayne

2019

Austin Bailey's carefree life is wrecked in the best possible way when a woman arrives in Lake Starlight with a baby she says is his. His huge family has opinions, but he only wants to change her mind about leaving.

3

Demise of a Self-Centered Playboy

by Piper Rayne

2019

A carefree playboy is shoved into responsibility after the death of his mentor and finds himself teamed with a difficult, tempting woman. Somewhere between chaos and reality TV, he starts changing for real.

4

Falling for my Brother's Best Friend

by Piper Rayne

2019

Running the family company is easier than resisting a tattooed playboy who also happens to be her younger brother's best friend. Living with him while her place is repaired only makes the problem worse.

5

Lessons from a One-Night Stand

by Piper Rayne

2019

A laid-back teacher realizes the sexy woman from a one-night stand is actually his new boss, the school principal. Trying not to fall for her becomes the hardest lesson of all.

6

Operation Bailey Wedding

by Piper Rayne

2019

Austin and Holly's wedding should be the event of the year in Lake Starlight. With the Bailey siblings and Grandma Dori involved, smooth planning was never really an option.

7

Confessions of a Naughty Nanny

by Piper Rayne

2020

An aspiring singer talks her way into a nanny job because a famous music producer has moved to town. The plan is to get discovered, not to fall for the man behind the music.

8

Operation Bailey Babies

by Piper Rayne

2020

Lake Starlight gears up for a triple Bailey baby shower, complete with family chaos, town gossip, and plenty of bets about who will have their baby first.

9

Operation Bailey Birthday

by Piper Rayne

2020

The Bailey clan comes back together to celebrate Grandma Dori's big birthday, with plenty of grandchildren, big personalities, and the kind of family noise Lake Starlight does best.

10

Rules for Dating Your Ex

by Piper Rayne

2020

Eighteen months after walking away while pregnant, a heroine comes face to face with the ex who never knew he had a daughter. Letting him back in might be good for their child and terrible for her heart.

11

Secrets of the World's Worst Matchmaker

by Piper Rayne

2020

A matchmaker realizes much too late that she is in love with her childhood best friend, the same man she helped pair with someone else. Keeping that secret gets harder with every wedding detail.

12

Winning my Best Friend's Girl

by Piper Rayne

2020

When the girl he never got over returns to town, one man decides this time he will not step aside. The problem is that history, friendship, and bad timing are still very much in the way.

The Baileys books in chronological order

  1. Book cover for "Lessons from a One-Night Stand"

    Lessons from a One-Night Stand

    by Piper Rayne

    2019The Baileys, Book 1
  2. Book cover for "Advice from a Jilted Bride"

    Advice from a Jilted Bride

    by Piper Rayne

    2019The Baileys, Book 2
  3. Book cover for "Birth of a Baby Daddy"

    Birth of a Baby Daddy

    by Piper Rayne

    2019The Baileys, Book 3
  4. Book cover for "Operation Bailey Wedding"

    Operation Bailey Wedding

    by Piper Rayne

    2019The Baileys, Book 4
  5. Book cover for "Falling for my Brother's Best Friend"

    Falling for my Brother's Best Friend

    by Piper Rayne

    2019The Baileys, Book 5
  6. Book cover for "Demise of a Self-Centered Playboy"

    Demise of a Self-Centered Playboy

    by Piper Rayne

    2019The Baileys, Book 6
  7. Book cover for "Confessions of a Naughty Nanny"

    Confessions of a Naughty Nanny

    by Piper Rayne

    2020The Baileys, Book 7
  8. Book cover for "Operation Bailey Babies"

    Operation Bailey Babies

    by Piper Rayne

    2020The Baileys, Book 8
  9. Book cover for "Secrets of the World's Worst Matchmaker"

    Secrets of the World's Worst Matchmaker

    by Piper Rayne

    2020The Baileys, Book 9
  10. Book cover for "Winning my Best Friend's Girl"

    Winning my Best Friend's Girl

    by Piper Rayne

    2020The Baileys, Book 10
  11. Book cover for "Rules for Dating Your Ex"

    Rules for Dating Your Ex

    by Piper Rayne

    2020The Baileys, Book 11
  12. Book cover for "Operation Bailey Birthday"

    Operation Bailey Birthday

    by Piper Rayne

    2020The Baileys, Book 12

Series background & context

The Baileys is one of Piper Rayne's signature series, and it is easy to see why. Set in the fictional Alaskan town of Lake Starlight, the books follow nine Bailey siblings who were orphaned years earlier and have grown into a loud, loyal, deeply entangled family. Each book focuses on a different sibling, but the real pleasure of the series is watching the whole family keep turning up in one another's business.

There is a lot of business to turn up in.

The romances cover a wide spread of setups, a teacher and a principal with a very bad first impression, a bride dumped by text, surprise parenthood, a brother's best friend, a tattooed playboy, an aspiring singer bluffing her way into a nanny job, and more. Around all of it are Grandma Dori, town gossip, busybody energy, and the kind of sibling closeness that makes privacy almost impossible.

Lake Starlight is not just a backdrop. It is a full small-town romance engine, quirky, nosy, supportive, and occasionally exhausting in exactly the way a good fictional town should be. Piper Rayne use it to give the books warmth, while the Bailey family gives them momentum. Even when a book follows a single couple, it always feels tied to something bigger.

The series also expands outward into later connected worlds, especially The Greene Family and Lake Starlight, so readers who start here get the clearest view of how Piper Rayne build a long-running shared universe.

If you want family-heavy romance with humor, heart, and a strong sense of place, The Baileys is a great entry point. These books read like comfort food with chaos on the side, and that is very much the charm.

Edited by

Richard Reis

Software engineer whose passion for tracking book recommendations from podcasts inspired the creation of MRB.

Anurag Ramdasan

Lead investor at 3one4 Capital whose startup expertise and love for books helped shaped MRB and its growth.

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