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Olivia Hayle writes contemporary romance with distinct, named series, each built to be satisfying as a single couple’s story, but more rewarding when you read a series straight through. Characters and friend groups recur, and later books can casually confirm earlier couples’ endings.
If you want the least guesswork: choose one series below and finish it before you switch to another.
A good place to begin
- Want her most “classic” setup (boss/workplace billionaire romance)? Start with Think Outside the Boss.
- Want a shorter, newer arc with a clear start and finish? Start with Best Enemies Forever.
- Want her newest series direction (relationship games/bets vibe)? Start with The Faking Game.
The Billionaire Games (read in order)
- The Faking Game: A carefully staged relationship starts as strategy, then turns into a problem neither lead can “manage.”
- The Marriage Bet: A high-stakes deal forces two rivals into close quarters, where pretending becomes harder than honesty.
Order note: This is the newest line, and it’s designed to be read from book one.
The Connovan Chronicles (read in order)
- Best Enemies Forever: Long-running tension finally gets tested when two people stop calling it “just history.”
- The Perfect Mistake: A single misstep becomes a slow, complicated shift into something real.
- One Wrong Move: One bold choice changes the rules, and the fallout becomes the romance.
Why order helps: the emotional backdrop builds as the circle tightens.
New York Billionaires (read in order)
- Think Outside the Boss: A career-driven heroine meets a boss who turns professional boundaries into personal temptation.
- Saved by the Boss: A rescue moment creates a connection that keeps showing up where it shouldn’t.
- Say Yes to the Boss: A forced-working-together situation turns into the kind of closeness that won’t stay convenient.
- A Ticking Time Boss: A deadline and a power imbalance turn attraction into a decision point.
- Suite on the Boss: Proximity and pressure strip away the “we can keep this simple” fantasy.
- 12 Days of Bossmas: A holiday setup delivers a quick romance hit with festive stakes and warm payoff.
Spoiler warning: later books assume you already know who ended up together earlier.
Seattle Billionaires (read in order)
- Billion Dollar Enemy: Enemies-to-lovers energy turns sharp when professional rivalry becomes personal.
- Billion Dollar Beast: A gruff, powerful hero meets the one person who won’t be intimidated into compliance.
- Billion Dollar Catch: A summer arrangement becomes a real attachment that neither planned for.
- Billion Dollar Fiancé: A past connection returns, and a “practical” engagement starts rewriting the future.
Reading tip: this series is especially cameo-friendly, so starting at book one keeps introductions clean.
Brothers of Paradise (read in order)
- Dark Eyed Devil: A ruthless, magnetic hero meets a heroine who won’t be moved by charm alone.
- Ice Cold Boss: Workplace friction turns into intimacy when control starts slipping.
- Red Hot Rebel: A rebellious streak collides with responsibility, and romance becomes the proving ground.
- Small Town Hero: A change of pace romance where community closeness forces emotional honesty.
Tone note: this line can feel more “family-and-legacy” driven; order keeps the sibling dynamic consistent.
Standalone novels (read anytime)
These are not part of the series above, so you can pick them up whenever the premise fits your mood.
- The Billionaire Scrooge Next Door: A grumpy neighbor romance that turns small moments into big feelings.
- Arrogant Boss: A workplace dynamic where ego meets its match and keeps losing ground.
- Look But Don’t Touch: Temptation, boundaries, and the slow unraveling of self-control.
- How to Honeymoon Alone: A solo trip becomes a reset, then romance shows up anyway.
Do you need a timeline order
No. Olivia Hayle’s books are best treated as separate series worlds, not one long timeline. The only “order that matters” is inside each named series.
Most recent and next book
- Most recent full-length release listed: The Faking Game
- Next release listed for the same series: The Marriage Bet (scheduled for 2026)
The simplest plan
If you want one clean path: start with Think Outside the Boss, finish New York Billionaires, then move to Seattle Billionaires. If you’d rather start newer, begin with The Faking Game and continue forward from there.
Frank is the editor of BookSeries.blog, focusing on publication order, chronological timelines, and spoiler-free reading guides for book series and fictional universes.