Most Likely to Match

by Ruby Barrett

Chloe is the one thing a matchmaker can't single. When her clients blame their failed dates on her unattached status she knows she needs help to save her business. Unfortunately, the only person that might be able to help her is the last person she ever expected to see Dean - the secret high school hook-up who's heart she broke, along with her own.

It might be petty, but Dean still hasn't forgiven Chloe after 15 years. When she comes to him seeking his infamous boyfriend-for-hire services, he laughs in her face. But to reach his own professional ambitions, he has no choice but to make a deal with her after all. As they become wary business partners, Dean and Chloe fight to ignore their fiery past.

But with their high school reunion around the corner, the woman voted Most Likely to Succeed and the man who got away, might find themselves getting schooled by their hearts.

Genres: Second Chance, Contemporary

222 pages, Kindle Edition

Published August 26, 2025

Reviews

[Elodie Colliard · Rating 5 out of 5]

Yes, the photoshoot scene will leave rent free in my mind for the rest of time. I want to hug Dean so bad 🥹

[✨Jessica✨ · Rating 5 out of 5]

“It’s so strange to be with a person you knew once. I am getting to know her again but also feel like I never stopped knowing her.”

⭐️⭐️⭐️⭐️.5 (rounded up for Goodreads)
🌶️🌶️🌶️

Chloe owns a matchmaking company but is starting to lose clients as they find out she isn’t in a serious relationship. Dean was her crush in high school until something completely awful ruined everything. 15 years later, he ends up in her life again and they have to work together for Chloe‘s business.

This story is a beautiful reflection on rebuilding trust when something went wrong in a relationship. Ruby has a way of writing delicious spice tension while having characters go through really meaningful situations. Chloe and Dean are messy and sweet and perfect. This was a quick read, but very satisfying.

Thank you to Ruby Barrett for the e-arc. All opinions are my own.

[Izzy · Rating 5 out of 5]

4.5⭐️!

[Stephanie · Rating 4 out of 5]

Going back to high school gives me the heebie jeebies but ruby made it seem so dreamy. I love the high school sweetheart second chance romance with Chloe and Dean. Also mildly enemies to lovers? All good things, all good things.

The healing in this book is so good! Good for them for doing therapy and working on themselves to be their best selves. And the spice!!! Amazing.

The pool! The confession booth!!!👏🏼 I loved this one.

[Jessica White · Rating 5 out of 5]

I need everyone to put Ruby Barrett on your radar. Her writing GLOWS in the minutiae of everyday life, pulling out the simplest and yet most profound moments and making them extraordinary. You don’t find many writers who can do this and also write humor and steamy scenes with as much deftness. I’m kicking myself for not having read more by her, because when the writing is good, it doesn’t matter what I tell you in the next few sentences about the plot.

There were so many moments of this that felt like a John Hughes film; adults at a high school reunion, school related trauma induced by the popular kids, and a little bit of the “beauty and the French tutor” opposites attract. Dean and Chloe used to spend more time making out than they did studying back in high school until a nightmare of an embarrassment happened to Dean (think showing up at school naked kind of dream, but worse). Dean left school and he and Chloe haven’t seen each other for fifteen years until he’s hired out as a photographer for a young business professionals event where she’s also in attendance promoting her matchmaking company. Needless to say their reconnection is rocky at best with distrust leading their emotions. It’s through them mutually needing the other as work partners that has Chloe and Dean begrudgingly teaming up and realizing they might actually like each other and carry some lingering feelings from the past.

This book is about forgiveness and doing so in a timeliness and manner that is right for you. I love how therapy was included (differently) for both Dean and Chloe and how Dean’s role as a dating counselor gave him the patience and grace to listen. At the same time, Chloe is able to right a wrong by being as truthful and open with Dean as possible even if it scares her anxious heart. The depth of emotions and longing in this book made me read late into the night, just wanting to spend all my time with this couple.

There’s a photography (and maybe bit of exhibitionist) component that is really beautiful. The first time Dean sees Chloe in 15 years it’s from behind the lens of a camera and in a way, the camera acts as a mirror that shows Chloe and Dean things they both do and don’t want to see. It lets Chloe feel beautiful and lets Dean feel comfortable and it’s fitting that their relationship both begins and ends with a photographed moment. This book is also sexy as hell. The scenes have purpose and feel so authentic to the characters; I loved that there are elements of sneaking around like teenagers afraid of getting caught making out right next to intensely erotic moments. If you’ve ever wondered what it would be like to have a more intimate relationship (in all meanings of the word) with your first love, you will love seeing how Chloe and Dean make it possible for second chances to rank high on the list of romantic tropes. Thank you to Ruby Barrett for my early reader copy. All opinions are my own.

Rating: 🌟🌟🌟🌟🌟
Steam: 🪭🪭🪭 (multiple scenes and detailed)
Tension: 🪢🪢🪢

[Abby Rose · Rating 4 out of 5]

4 ⭐️

Thank you to Ruby Barrett for the opportunity to read this ARC! All opinions are my own.

Spicy, sweet, and filled with humor and tension, “Most Likely to Match” tells the story of Chloe, a matchmaker who’s business, Core Cupid, is starting to hemorrhage clients. As a perpetually single woman, most clients don’t see Chloe as the best person to help them find their perfect match. In steps Dean, Chloe’s secret high school FWB who’s heart she broke and life she ruined. Can Dean help Chloe salvage her business, and can they find each other again in the process?

It’s hard to explain Ruby Barrett’s writing if you haven’t had the privilege of reading one of her stories before. She crafts characters who feel so real and raw! Chloe played such a huge part in the events that changed Dean’s life and gave him so much trauma, and they both had so much baggage because of that. Ruby doesn’t sugar coat feelings or situations and breathes life into her characters that pull you into the story from the first chapter.

I’m not usually a huge fan of second chance romance, but Dean and Chloe were never able to be with each other the way they wanted to in high school. They had so much love for each other in both the past and the present! It was wonderful to see them be open and honest with each other, even through the toxic patterns they were trying to break out of. They weren’t the same people they were at seventeen, and the growth that they both had was so inspiring.

And I have to mention the bromance between Nick and Dean! I loved the scenes they had together. And also the pool scene… I won’t elaborate because you need to read the book and see for yourself! 😉

[Shannon · Rating 3 out of 5]

The second in Canadian author Ruby Barrett's Toronto based The Matchbooks series, sees matchmaking app creator, Chloe lamenting the fact that she keeps losing subscribers because she doesn't have a 'perfect' match herself.

In fact Chloe's never even tried to date before after her first secret high school love with her French tutor, Dean ended so tragically and traumatically for them both. This book dealt with a lot of heavy emotional issues and I liked that Dean grew up to be a therapist and side-hussle photographer but I kind of felt like his and Chloe's reunion years later was a bit rushed and not entirely healthy.

I don't know, this was definitely very spicy and a fast read but I'm not sure it'll go down as a favorite for me by this author and overall in general. If you're looking for something spicy set in Toronto and don't mind heavier issues involving public shaming and getting caught naked this might be more for you.

[Betts · Rating 5 out of 5]

4.5 ⭐️
I was surprised by how emotional it was, it brought a tear to my eye every now and then, because both Chloe and Dean were so vulnerable.
Something I really liked was that it felt very millennial, and the fact that the two of them always loved each other, and were able and willing to give each other a second chance.
A sweet but emotional case of "it was always you."
I had only read a couple of Ruby's short stories and they were good, so I was excited to read a full lenght book of her, I'm glad i finally did it! I'll definitely will read more of her backlist 💖

Thanks to the author for the free eArc

Every time they remembered something that happened when they were teenagers, I wanted to jump into the book and hug them, especially Dean

[Laura VanZant · Rating 5 out of 5]

When I tell you it’s my favourite thing Ruby’s ever written…

I love a good second chance romance so obviously “Most Likely to Match” was going to be right up my alley. But it ended up speaking to my type A, Virgo, eldest daughter soul on a spiritual level.

These two are both so incredibly romantic and so incredibly hilarious. The author’s voice shines through her writing, and I was both in stitches and in tears while I read.

I hope you fall in love with Chloe and Dean as hard as I did 💙

*ARC received in exchange for an honest review, all opinions are my own

[Trianna/Treereads · Rating 4 out of 5]

I love Ruby Barrett's writing so much!!

More thoughts to come!

*thanks to Ruby Barrett for the gifted eARC; all thoughts are my own*

[Nicole Moon]

loved this 💕 emotional, meaningful, steamy, messy, sweet and more. it's second chance, forced proximity, and healing through a lot of things

[Nicole (NicoleIsBooked) · Rating 4 out of 5]

Full review coming soon!

[Sofia · Rating 5 out of 5]

MOST LIKELY TO MATCH is easily one of my top books I’ve read so far this year. If I ever become a fictional character, I hope it's Ruby that writes me into existence. Both Chloe and Dean are flawed and a little messy and a little broken, yet Ruby handles both of them with such care and obvious love from page 1 that even a few chapters in, you know that they’re both going to be okay. I love a second chance romance, and Ruby has given us this perfect little gift full of tenderness, love, and some really great sex.
Throughout the whole book, I loved how much Chloe and Dean both grew in their own journeys; Dean in becoming his own person, strong and confident, while also learning to trust Chloe and everything that goes along with that; Chloe in finding herself again and again, pushing herself to be someone Dean can trust, and going out of her way to show this to not only Dean, but to his loved ones as well. I love them!!
All the emotional stuff aside, Ruby is the master of spice. Hot spice. Spicy spice. (Again, if I ever become a fictional character, Ruby better be the one to write my story!!) *insert shitpost that says “Dream blunt rotation but I’m the one being passed around”*

5 stars Ruby Barrett please write forever!!

[Jess · Rating 4 out of 5]

estranged lovers to lovers, all written with Ruby Barrett’s trademark style

Thanks to the author for the complimentary ARC. All opinions provided are my own.

Ruby Barrett’s The Friendship Study & The Romance Recipe were some of my fave books during their respective release years. While I wasn’t always 100% sold on some aspects of the plot in Most Likely to Match, I was totally a goner for how Barrett writes the leads’ emotional & physical chemistry. It was Hawt.

Dean & Chloe used to hook up until he was publicly humiliated & Chloe didn’t support him as she should have. Flash forward years later, when they reconnect.

Though some of this premise didn’t totally work for me, I was able to get past it. Mostly because I loved so many of the moments of their journey. It was stunning in lots of ways.

Barrett has this way of writing books that are bursting with chemistry, & yet languid & lovely in how they describe the overwhelming rightness of the leads together. This one wasn’t perfect but lots of parts in it were for me.

4.5 ️stars, out 08/26.

Please see a trusted reviewer’s list of CWs.

[Mel · Rating 3 out of 5]

I wanted to love this book and it came real close for me but in a lot of ways, it kind of skimmed the surface on things that I wish it had delved a bit deeper into. First of all, that prologue made me real nervous and I wasn't sure I could get behind the FMC but thankfully, I did find myself able to get on her side. However, there are at least two mentions of the MMC having a semicolon tattoo which I believe is an indication of depression or anxiety or self-harm/suicidal ideation. Two different people make note of Dean having this tattoo, including FMC Chloe but there's never any real exploration of all that Dean endured in the aftermath of the events of the prologue. Yes, he's got some emotional hangups due to what happens to him in high school and he's in therapy but there's a lot of ground to cover between that and having a semicolon tattoo. I liked the romance well enough and of course, Ruby Barrett knows her way around a sex scene so all that was good but I guess I just wanted more in terms of character development.
Content Notes: MMC is publicly humiliated in high school in a very traumatic way.

[Vanessa Symington · Rating 4 out of 5]

Most Likely to Match... more like most likely to make me swoon.

This was charmingly messy. A second chance romance with spice and plenty of emotion. From a secretive high school fling to a falling out to reconnecting 15 years later, Chloe and Dean find themselves falling back into each other's orbit. This story captures the struggles of confronting the past while also being in the present. It is about rebuilding trust and establishing a meaningful relationship.

Ruby Barrett has done a fantastic job at balancing relatable human emotions with witty banter, spicy moments, tension, and some nostalgia (because yes, I was transported back to high school at various points throughout this book). I enjoyed every single moment.

**Please be mindful of TWs and CWs prior to reading to make sure this is a fit for your reading tastes**

[Georgie · Rating 4 out of 5]

“I've felt different for a while. Different in ways that were subtle at first, but now..." I spread my arms wide. "Now I feel it everywhere. All over. And it's wild to me that no one else can see it, you know? I keep going about my days. I eat the same foods, wear the same clothes, follow the same skin care routine and running paths, but I'm not the same. I'll never be the same again." I press my hand to my chest. The same place he put his that night in the parking lot. "That's Dean.”

RIGHT. IN. THE. FEELS. She’s done it again folks!!

[Sam-TRN · Rating 5 out of 5]

a second chance for love in Toronto? yes, please

What I liked about this contemporary story:

⭐️ Former high school sweethearts
⭐️ Second chance romance
⭐️ Rebuilding trust after betrayal
⭐️ Modern matchmaker x photographer/boyfriend for hire
⭐️ Healing and growth
⭐️ Set in Toronto, not the usual setting
⭐️ Second book in a series of interconnected standalone stories

Loved it very much and can’t wait to read more of Ruby’s stories.

[Brian Brown · Rating 4 out of 5]

Both books in the series have a lot of beautiful, lively human detail. Makes it very easy to feel with and through the characters - every other book by this author has the same, consistent quality. That takes work, imagination and attention - and it pays off for the reader. Both books aren't perfect though, and this author has some near-perfect ones.

This one I liked more than the previous one, maybe because it plays more into my sensibilities.

[Chrissie · Rating 4 out of 5]

Did I really read a Ruby Barrett book if I didn't cry at the end from how sweet the couple are?

[Kaitlyn · Rating 4 out of 5]

Ruby always writes such fun books with good spice! Full rtc

[Juls · Rating 3 out of 5]

3.5⭐️ I really enjoy this author’s writing but the story in itself was too simple for me, not boring but just really plain.

[Katie Hodgie · Rating 5 out of 5]

Ruby Barrett can do no wrong!

[Ryann Froats · Rating 2 out of 5]

I love a Canadian author, but this just felt bland

[Allissa · Rating 3 out of 5]

3.5*

[Linda Watson · Rating 3 out of 5]

God the second hand embarrassment was all over this book and made it really hard to get through. The pacing seemed off but the end was lovely.

[susana ♡ · Rating 5 out of 5]

I don’t even know how to start this review because all I want to say is: this was perfect. Ruby always delivers the most meaningful HEAs, and this one was no exception.

After Chloe and Dean’s friends with benefits situation in high school ended in a terrible heartbreak that rightfully shattered Dean’s trust, it took him a while to trust Chloe again. Her guilt was just as heavy, so this story was all about forgiveness, healing and learning to trust again.

Reuniting after so many years rekindled the flame between them, but it also brought back those unresolved feelings. I loved the maturity in the writing and how Ruby handled the conflict. Dean’s pain and mistrust were hard to read at times, but that’s how it felt real. The physical intimacy played a big role in their development and I love how significant it was. Overall, the book as a whole was tender and beautiful.

Ruby’s such a magnificent writer. I hope she continues delivering these beautiful and emotional stories 💙.

Rating: 5/5
Steam level: Open door, +5 scenes, high level of detail

ARC provided by Ruby Barrett. Opinions are my own!