This is the second book in the series and you need to read What I Should've Said first or you will be spoiled.
It should be noted that I received an arc of this book, so changes may be made before it is published.
I loved the beginning and end of the book. The middle felt more like a retelling of Norah and Bennett's story than one of Josie and Clay. I would have liked more focus on them.
This is the story of Josie and Clay who fall madly in love and get married but then a series of events transpire and Josie asks for a divorce. For five years they avoid each other and then are forced to face their relationship and why Josie asked for the divorce.
Five years felt like longer than Clay would have let pass without fighting for her based on his personality.
Overall, I really enjoyed both Clay and Josie.

I was so excited to be able to read Josie and Clay's story. The anticipation from book one was so high for me. I loved their instant love/romance connection. I really wish there was more of it...the love from the beginning. I understand that would have made the book quite a bit longer, but I think that would have given my rating an extra star. The tension and the love was palpable for sure. I really loved being able to get more of Summer's 'story' intertwined into this book as well. Overall, I was very pleased with this book and am glad I was able to review it ahead of time!

I am not a fan of the second chance trope. It might be my own life and experiences, but it's not usually my go to. However, a Max Monroe book is always my go to. I loved What I Should've Said, and I loved When I Should've Stayed. Max Monroe said "it has the lowest of lows and the highest of highs." They were right. This book is heart wrenchingly, stunningly, hilariously well written. I wanted to keep reading and stop reading at the same time. There are a lot of elements of grief that makes it tough to keep reading, but mostly in a cathartic way. I loved Josie and Clay's story. I loved revisiting a small town that reminded me of Stars Hollow, Schitt's Creek, Pawnee, and Bluebell. I love that the town has fleshed out, real characters that add to the story. I liked seeing different perspectives of Norah and Bennett and Summer's story. This book is just as heartbreaking. But it is also just as uplifting and hopeful. I was lucky enough to receive an ARC of this book. Have tissues, pink sunglasses, and maybe some white wine available while you read it.

Thank you @netgalley for the ARC of this book!

𝐖𝐡𝐞𝐧 𝐈 𝐒𝐡𝐨𝐮𝐥𝐝’𝐯𝐞 𝐒𝐭𝐚𝐲𝐞𝐝 𝐛𝐲 𝐌𝐚𝐱 𝐌𝐨𝐧𝐫𝐨𝐞
𝗠𝗬 𝗥𝗔𝗧𝗜𝗡𝗚: ★★★

First let me say I am a huge Max Monroe fan! I have loved all of their books so much up to this point and while this wasn’t my favorite it was still good.

The main reason this didn’t work so well for me was because I read this book right after reading What I Should’ve Said. That book was everything! An easy five star read that I would consider giving all the stars!!!

75% of this book was pretty much just a retelling of that same book but from different character POV’s. I was honestly bored since I literally had just read the book.

Also this book jumped timelines constantly, and was very choppy when doing so. This made it very hard to connect with the two characters of this story. The depth and emotion in their story felt lost because right as I was starting to understand something or connect it would jump to another time leaving me rather confused.

I know this all sounds a bit harsh but I do think this would have been much easier to read if I would have spaced these books out a lot more. I was looking for the depth and connection like in the first book that I had just finished and this one just didn’t compare.

I knew returning to Red Bridge would break my heart, but yet again, Max Monroe surpassed my expectations!

They manage to write such dynamic characters and such a dynamic town, while keeping it realistic enough to make it feel familiar.

This book, we explore Josie and Clay’s relationship, which we saw some of in What I Should’ve Said. The book is scattered into two parts: before the moment and after the moment, with the before showing us the relationship and marriage and the after showing us how everything fell apart.

As usual, please check the tag warnings because the book deals with some hard hitting, real life topics, and deals with them very well. I’m definitely buying this one for my shelf and can’t wait for what comes next out of Red Bridge (I’m hoping for a Breezy book!)

Thank you NetGalley and Max Monroe for an ARC copy of this book!

Max Monroe delivers a deeply emotional, character-driven follow-up in When I Should’ve Stayed, the long-awaited second installment in the Red Bridge series. This isn’t a simple love story—it’s about heartbreak, silence, sacrifice, and the brutal work of clawing your way back to the person you thought you lost forever. If you read What I Should’ve Said, you know Josie Ellis and Clay Harris carry a complicated history. This is that history, and it’s messy, raw, and sometimes hard to read.

The novel unfolds across a dual timeline: Josie narrates “Before the Moment,” and Clay takes over in “After the Moment.” Their voices, distinct and emotionally layered, guide the reader through the past and present, stitching together a love story that was never really over. This structure can be disorienting at times—the timeline jumps frequently and without consistent anchors—but it reflects the nonlinear way grief and regret often play out in real life. The storytelling is intentional and immersive, but it asks the reader to work for their footing.

Josie is the kind of heroine who splits a room. Some readers will relate to her stubborn silence and protective self-isolation; others will be frustrated with her choices and lack of communication. Her decision to leave Clay—and to stay gone for five years without ever truly explaining why—feels unforgivable until you see what she’s carrying. Her trauma is immense, her guilt even heavier. And though she’s not always likable, she is honest in her pain. She believes she’s doing the right thing by keeping Clay in the dark, and that belief is both her greatest strength and her deepest flaw.

Clay, on the other hand, is easy to love. He’s the heart of this book. A golden retriever in human form, Clay is loyal, tender, romantic, and devastated. He never stops loving Josie, not even after she walks away without warning. He doesn’t understand her silence, but he respects it. He’s angry, yes—but mostly he’s heartbroken. And yet, even in the lowest moments, he doesn’t let go. His love is unwavering, to a fault. And while some might wish he showed more resistance, more bitterness, there’s something powerful about a man who chooses patience over pride. He doesn’t need to be loud to be strong.

What makes this book shine is its emotional precision. Max Monroe writes with devastating clarity, cutting through cliché and fluff to land straight in your chest. The dialogue, the internal monologues, the aching pauses—all of it feels real. And while there’s a thread of small-town charm—quirky locals, nosy neighbors, a rogue sheep—it never overshadows the emotional weight. This is a book about love, yes, but more so about what we do in the name of love, and how sometimes that means making the wrong choices for what feels like the right reasons.

One of the biggest challenges here is the pacing. The bulk of the book is spent in the past—how Josie and Clay met, fell in love, and fell apart. Readers waiting for the reconciliation, the present-day healing, will need patience. When the story finally returns to the now, it’s in the final act. Their reunion, while satisfying in its emotion, is brief. It could have used more time to breathe. After all the heartbreak, we need more of the healing.

Still, it’s a powerful story. Not just about a couple who lost their way, but about grief, trauma, and the quiet ways we destroy ourselves thinking we’re protecting others. There are moments that will make you cry—especially those surrounding Summer, a character whose loss casts a long shadow over the series. And there are moments that will make you laugh, often courtesy of the vivid supporting cast. But above all, there’s heart in every chapter. Even when it’s breaking.

When I Should’ve Stayed isn’t easy. It’s not light or quick. It demands your attention, your emotional investment, and your grace. But if you give it those things, it gives back tenfold. It hurts in all the right places—and heals just enough to make the journey worth it.

Max Monroe isn’t just telling a love story. They’re telling a story about what it costs to lose one—and what it takes to try again. Read What I Should’ve Said first. Then get ready for Clay and Josie to wreck you, one regret at a time.

This book was amazing!
Clay and Josie’s relationship was a rollercoaster of emotions. They fell in love hard and fast, but so much else transpired that you really don’t know which way the book was going to go!
The banter and chemistry between the characters was unmatched.
I laughed, I cried, I swooned.

Absolutely a bittersweet story of Clay and Josie! I love the way this one tied into What I Should’ve Said! The POVs and timelines that’s gave us all the details, unraveling everything we needed.there is just something about these characters and this town that I am so in love with! It gives Stars Hollow but there is something so much more underlying here. I can’t get enough Red Bridge and can’t wait to scoop up a physical copy in July

When I Should've Stayed is a beautifully written second chance romance. Following the characters of the first Red Bridge book, What I Should've Said, Josie and Clay find their way back to each other after a long bought of turmoil, life, and other miscellaneous circumstances. While the book follows the characters of book one, it can be read as a stand alone. However, you don't want to miss out on the goodness that both books brings. Max Monroe did a wonderful job with the plot, characters, and filling in this book.

The characters were lovable and relatable. The plot brings you to a world where even though bad things happen there's a happy ending. As someone who's currently struggling with a case of bad juju, I can appreciate a series of misfortunate events only to arrive with a light at the end of the tunnel and a happy ending.

I can't say I loved the dual timeline, it took some time to reorient with what I was reading and when but it didn't take anything away from the story.

Overall, I wish I could give half stars because I don't feel like a 4 star gives this book enough credit. I'm hoping there's a book three with Breezy.

I gave When I Should’ve Stayed 3.5, rounded up to four ⭐️⭐️⭐️⭐️ Thank you MaxMonroe for the ARC. These are my honest opinions.

I met Josie and Clay in What I Should’ve Said (Norah and Ben’s book) and couldn’t wait to read their story.

I didn’t like this book as much as I like What I Should’ve Said. I just loved Norah’s quirky personality and her and Ben’s love story. Josie wasn’t as much fun as Norah. I didn’t care much for Josie as a person in parts of the book. I adored Clay though! And they didn’t waste any time on the intimacy department - I prefer the slow burn of Norah and Ben’s story.

I also wasn’t a huge fan of the timeline going back abs forth. Normally, this doesn’t bother me, but I don’t think it was as clear in this book as it could have been.

Overall, I enjoyed reading this!

This is my second Max Monroe book. I read What I Should’ve Said last year and really enjoyed it.
When I Should’ve Stayed has overlapping timelines with the first book so there will be better appreciation if you read the former.
This book follows Norah’s sister Josie. This gives a backstory of what really happened with Clay and Josie in the first book.
This is dual timeline, dual POV, second-chance romance.
In typical Max Monroe fashion, there will be heartbreak and explores really heavy topics.
Overall, I liked it. The writing is digestible and very easy to follow. I give this a solid 3.5⭐️

Thank you to NetGalley and the publisher for the opportunity to read this arc.

I love Max Monroe books. Each one I’ve read I’ve always given honest glowing reviews and recommendations that they deserve to all my book friends. For the first time, I can’t do it because I didn’t finish the book.

Reasons why I DNF:
-the different time jumps (before, after, part I, part I….) why? I didn’t like that at all and hard to follow along with what was going on in the plot.
- I didn’t not like Clay. He went 0-100 in liking her so quickly. Just something about him gave me the ick.

Perfect follow up from the first book. Clay and Josie’s story gave me so many emotions. I love that there were many mentions of summer from the first book and you got to see her story a little bit through Clay and Josie’s eyes. Max Monroe is my favorite. They have a brilliant way with words.

The perfect follow up to What I Should've Said! I loved Josie and Clay's story so much. I laughed, I cried a little, and I couldn't help but root for them from the very first page. In typical Max Monroe fashion, this was written so well, it was so easy to just fall into the story and not even realize that I was 100 pages on before I knew it. Such a heartfelt and easy read!

I’ve been waiting for Josie and Clay’s story since we met them in book 1. I knew their story would be intense, but holy moly what a story. I was not prepared going into it and to relive Summer’s passing…I have no words. That little girl had everyone rapped her fingers, she was the happiest, kindest, most loving little kid. The love Josie and Clay had for her, it was like she was their own.

Clay knew from the first moment he spoke with Josie in his bar that he would do anything to get her to go out with her. She was the most beautiful thing he had ever seen and he knew that she was his other half. He wasn’t looking for a relationship and was happy with his life, but once he met Josie he knew he could not live without her. After she agreed to go on a date with him they were inseparable and one day hopefully very soon he would make her his wife.

Josie had been through so much tragedy and loss. First her father, then her little sister and at 18 years old when she decided to leave her toxic mother and move in with her grandmother, she lost contact with her middle sister. Josie’s first priority was always her grandmother, she was basically all she had left and would do anything for her. But that all changed when Clay came into her life. Now she had someone that loved her in a way she has never been loved by anyone. He would give her the moon and stars if he could. She was all he saw and needed and she knew that. But it was getting harder and harder for her to leave her grandmother to spend more time with Clay.

Choosing between family and the love of your life is hard, but add loss and your life can flip upside down. Josie felt like she was drowning and everyone around her was leaving her or getting hurt. She couldn’t see an end where she and Clay would be happy and she can give him everything he wanted in life. So she made the difficult decision to let him go. She would never be able to move on but he had to, he has to move on and get everything he deserves. The only thing was that Josie couldn’t see that the only thing Clay ever wanted was her, nothing else. If he had her by his side, then nothing else mattered, but how could you show and explain that to someone when you don’t even understand why they left you in the first place.

For 5 long years he tried everything he could to get her to open up to him, to work it out, but was there to much loss and sadness to move one? Would she be able to see that their souls were meant for each other and all they needed to survive and live was each other?

Received this ARC for my honest review and opinion.

When I Should've Stayed is a bright light drowning in heartache. From haunting emotion to neverending romance, Monroe knows how to break a heart in the most captivating of ways. Clay and Josie wrap the soul in little moments. Endearing and heartbreaking collide with explosive results.

Get your tissue ready because you are going to cry, laugh, cry and fall madly in love with Clay and Josie!

Wow…just….(wipes tear)…this is one of the most gut wrenching yet beautiful stories I have read in awhile.

Josie and Clays story spans a few years and I loved how these two amazing authors wrote their story. It was easy to follow and everything flowed beautifully. If you haven’t read book one just be warned it will be spoiled.

I love how much Clay loves Josie. It’s a steadfast forever kind of love that doesn’t give up. He is the rock Josie deaerves and needs and their journey is a tough one but the love they have is worth the fight.

Another great read from Max Monroe but definitely another tearjerker, especially reliving the events of What I Should've Said. Clay and Josie's story was well worth the journey.

Max and Monroe, I don't know what gets into your mind when you write these books but this series especially pulls every heartstring I have. I cried throughout this book but only because I was so moved by the story and the flashbacks from the previous book. I will think about this series for years to come because it just sticks to me.

I am so glad I got to read this book before it was released because I was so looking forward to it. This couple is everything and it was so nice to see how their story played out.

If you do not get into this series you are missing out. The characters and the stories are just amazing.

Prepare your tissues, fellow Max Monroe fans, because When I Should've Stayed is an absolute masterpiece of emotional storytelling! As someone who devours everything they write, this book hit me right in the feels and reminded me exactly why I love their work so much.

This isn't just a second-chance romance; it's a heart-wrenching, beautifully messy journey through the "before" and "after" of Josie and Clay. The dual timeline and dual POV were expertly handled, slowly unraveling their history and showing us every agonizing step of their separation. I was on the edge of my seat, desperate to understand what went wrong, even as my heart ached for them.

And can we talk about Clay? Oh, Clay! He is the ultimate golden retriever MMC – swoon-worthy, devoted, and just an absolute dream. His love for Josie is so palpable, so unwavering, it practically leaps off the page. Even when Josie was making choices that made me want to pull my hair out (bless her strong, kick-butt heart, even if she could be a little frustrating at times!), Clay's unwavering affection was a constant, shining beacon. Their connection is pure electricity, even through the heartache, and that's the magic Max Monroe always delivers.

This book is an emotional rollercoaster in the best possible way. It delves deep into loss, sacrifice, and the brutal reality of growing apart, but it also celebrates the enduring power of second chances and unconditional love. If you're a fan of angsty, deeply emotional romances that will make you cry happy and sad tears, and if you live for a devoted hero, then you absolutely need to dive into Josie and Clay's story. Just make sure you've read What I Should've Said first to get the full, glorious picture!