First and First, The Five Bouroughs Series by Santino Hassell


Caleb Stone was raised on the Upper East Side, where wealth and lineage reigns, and “alternative lifestyles” are hidden. It took him years to come out to his family, but he’s still stuck in the stranglehold of their expectations. Caleb knows he has to build his confidence and shake things up, but he doesn’t know how… until Oliver Buckley enters the picture. Oli is everything Caleb isn’t—risk-taking, provocative, and fiercely independent. Disowned by his family, Oli has made his own way in the world and is beholden to no one. After a chance encounter on New Year’s Eve, Caleb is smitten. As Caleb sheds the insecurities that have held him back for years, he makes bold steps toward changing his career and escaping years of sexual repression. But for Caleb to take full control of his life, he has to be brave enough to confront his feelings and trust Oli with his heart.

We received an early copy of First and First from the ever generous Santino Hassell who has also provided some of the beautiful pictures we have used in today’s blog to celebrate his latest release.

Spoilers ahead – read this great book first then come and have a chat about it with us.

FRA: First and First is the third installment in Santino Hassell’s Five Boroughs series: a realistic account of the start of a relationship set against the scintillating set that is New York City.

I sound like a broken record: characterization and world building are the sharpest tools in Hassell’s writerly tool box. His characters’ arcs feel realistic and the NYC that shines through the pages of these books is in turns gritty and light filled, a comfort to his characters and at times an obstacle and manifestation of their turmoil.

Where Sutphin Boulevard explored the journey from friendship to love amidst some very serious issues and Sunset Park pitched two seemingly wildly different characters against each other in a flurry of young love, stereotyping and breaking of barriers; First and First conveys the start of a relationship between two men coming at even the concept of a relationship from two very different angles.

I particularly loved the characters’ growth and change as they get close, tear themselves apart from each other and come at each other again from a completely new angle.

I want to spend two minutes patting my back: remember in our Sunset Park review when I said “Now, I have a feeling that, as readers, we were supposed to dislike Caleb, there were hints of Caleb being manipulative: I don’t buy it.”  well, am I ever so grateful I called it, because I was so right: there’s nothing inherently wrong with Caleb. He is not manipulative but insecure – our perception of Caleb was completely coloured by David’s opinion and expectations.


MIKI: I second that. I didn’t like David´s character at all. Not in the first book or in the second one. So his small appearance was appreciated because it allowed Caleb´s character to shine and develop without the constraints of David’s POV.

FRA: Caleb was not manipulating David, Caleb was trying with all that he got to fit in the gilded box bread of the heavy expectations built by his family and environment. Out and proud David, provided a modicum of rebellion to a man forced into a shimmering closet but also the safety of a solid “relationship” based on all the points in a pre – determined checklist.

I felt really, deeply sad for Caleb – well, not for his super privileged upbringing in the 1% of which I can make no remarks because miiiiiles away from me and my experience – but because he is so trapped, so dreadfully unable to take even one step for himself without checking against the boundaries of his upbringing. He has built his life of expectations and seems intent in checking all of the boxes on the “list of life milestones according to the Stone family”.

The loss of his relationship with David and the loss of his job set Caleb on a course for radical change – change he doesn’t seem to even consider  he is undergoing until his whole world is shaken by Oli Buckley.

Oli (he who, you might recall, I shipped something fierce with Ray) is in many ways Caleb’s opposite – from the same 1% stock as Caleb, he broke the rules by unapologetically coming out in the most spectacular fashion, got disowned and thrown out for it and has taken all the steps not only to break free from his privileged, silver spoon upbringing but also to set his own course, to be his own man. I think his fierce sense of independence is at the core of his determination not to commit to a relationship, although with the way he pursues Caleb from the beginning at times his no commitment rule seems more like posturing than anything else.

I must say I loved the way these two interacted and ended up changing each other, I also think that under the layers of life’s different experiences these two men are both lonely and barely containing an energy, an innate desire to affect changes in spectacular ways.

I also love that there’s a common thread about families and their interactions in the whole series so far – one I hope continues to be explored in the next books. All parents’ sets in the books fail these men one way or the other: abandonment, mollycoddling, indifference, judgment (gods wasn’t Caleb’s mother the most judgey of judgey mothers ever? She was so judgey I almost called her mum) and yet siblings step up to the plate, friends become the family they chose for themselves. Even if, at the first look, some of the relationships seem very shallow, I do think that there’s a pull, a thread between all of the characters and it is this thread that gives the author the possibility to develop the story not based on major plot development but certainly on the major growth and development of his protagonists. The fact that we gleam glances of the previous couples – Michael and Nunzio, and more interestingly for this particular installment, Ray and David – keeps the thread present, if not prominent, enough for readers to feel connected both to the present story and the series at large. It is subtly done and I think it works very well from a narrative perspective.

MIKI: I thought that the characters were believable even if I personally don’t necessarily identify with them because we are on opposite sides in terms of cultural roots, families, money, social status. Etc. But the vulnerability they show in that context is super enjoyable and well delivered.

FRA: I agree Miki, at a visceral level I could relate with many of the innerworks of both Caleb and Oli: from the “work” speak about API and building new technology to the loneliness and the breaking of family ties before moving on to become their very own people. I got it, I empathised. And if – by genetics alone – I am unable to comment one way or the other on the intimate relationship between Oli and Caleb (aside from oh, ugh, is it getting hot in here or is it just moi?) I can 100% stand behind the mighty ritual dance of two grown people around the ever present fear of vs need for commitment in relationships for 30 somethings all over the world.



In this context, that is in the context of an adult relationship with all its complexity and rituals I did think that Oli’s  “I love you” was a bit sudden. I mean, I would have been happy with these two poised on the verge of a serious and committed relationship: the book narrative journey railed them in that direction, as readers we did our job and read between the lines of Oli’s stubborn unrest – there was no other course for these two men but convergence into a stable, shared reality -a happy ending without the need for utterance of the three words.

MIKI: I feel that the final declaration of love and the inevitable HEA were unnecessary. Especially taking into consideration their previous behaviors in the book and Oli’s reluctance to any commitment, so the sudden change of mind was a bit out of the blue. In all honesty I feel this book would have been perfect with a not so perfect ending.

I enjoyed First and First a lot more than Sunset Park, I feel it still didn’t carry the profound story and character development of Sutphin Boulevard and Hassell´s previous books. First and First held that essence when I started reading it, but the necessity for a HEA and for *closure* of every thread, put the book back in the pile of “those romance books which romance publishers approve of as much as the “target” audience does”.

FRA: I loved First and First, I found it romantic, realistic, well set into its contemporary background and incredibly well written. I totally see what you are saying Miki, although from a story perspective it didn’t bother me more than it felt like an unnecessary  stumble in an otherwise flawless narrative.

I think this book is way above the standard romance fare out there right now and I highly recommend it.

Santino Hassell is a talented author, one with  the potential, for sure, for changing the current Romance landscape one great book at the time.

First and First is book three in the Five Bourough Series, it is out today and you can find it at:








Five Boroughs series:





4 thoughts on “First and First, The Five Bouroughs Series by Santino Hassell

    1. Hi Nehaa thank you for commenting. I have indeed read the rather splendid ICoS around 4 years ago. We are all big fans of that series and it makes us super happy to see so much love for both ICoS and Ais and Sonny as its authors. Thank you for reading our posts!

      Liked by 1 person

      1. They are also among the longest books I’ve ever read. It took me two days strainght to go through the whole series day and night with hardly any sleep. But I just could’nt help myself!


      2. Eh I know the feeling! Masterful story telling, incredible world building and exceptional characterisation and a edge of your seat story line. I loved that they were so long. I have reread them many many times and the series is in my top 3 of all times!

        Liked by 1 person

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