Winging It With You by Chip Pons Review

Catching flights . . . and feelings.
 

Asher Bennett thought his relationship was just fine. Until he’s unceremoniously dumped at the Boston airport ahead of The Epic Trek, the worldwide travel competition reality show. Armed with only a ticket and righteous indignation, Asher finds solace at an airport TGI Fridays. Luckily, right in front of him is a smooth-talking airline pilot ready for takeoff.
 

Theo Fernandez has been grounded. He’s the only pilot that has never taken a vacation and the edict has been passed Prove you're prioritizing work-life balance or say goodbye to your wings. Struggling to bask in his new downtime, he stumbles upon the perfect opportunity. The handsome guy at his favorite terminal eatery has a sudden opening for a partner . . . on a nationally televised reality show.
 

As Theo and Asher buckle up to fake date for the cameras, the undercurrents of attraction make them wonder if their on-screen chemistry hints at something bigger. But do they have the courage to leave their baggage behind for another chance at love?

An Amazing Race-style reality TV competition, an airport breakup + hot pilot meet-cute, and the good ol’ fake dating + forced proximity tropes, Chip Pon’s M/M romcom Winging It With You is a vibe. A perfect summer read mixing international travel destinations with romance trope hijinks, Pon’s trade publisher debut is a fun, light-hearted yet comforting story. Featuring lots of laughs, embarrassingly awkward moments, spicy scenes, yet a lot of heart, Winging It With You is the type of book that will make your day just a little bit brighter or leave a smile on your face with its endearingly sweet and cute story.

I openly admit that I am a huge fan of the Amazing Race and have been watching it for years, so when this book randomly popped up in my Instagram reel suggestions I was intrigued. An Amazing race-style reality show paired with a fake dating M/M romcom, the algorithms are getting scary good these days. Comically over the top right from the start, Winging It With You makes it clear that it’s a story written for pure, unadulterated enjoyment and a good time. Rather than coming off as derivatively tired, Winging It With You wears its tropes on its sleeve cheekily and proudly, crucially avoiding off as cringy. From Asher and Theo’s conveniently timed and humorous meet-cute, to the one bed trope, to embarrassing reality show interview clips, the story hits many familiar narrative beats yet somehow still feels fresh due to its gay twist. Although the story is largely predictable, it’s almost comforting how smooth and natural Asher and Theo’s shift from awkward strangers, to partners in faking crime, to something real is. In author interviews and notes, Chip has stated that with this book, he set out to write a fun and wholesome romcom that’s easy to enjoy and not too heavy to read. As such, most conflicts between the Asher and Theo are resolved quickly and while there’s certainly stress and tension involved, it’s almost entirely of the catching the feels and romantic pining variety rather than personal or ugly drama.

Although Chip himself has mentioned in interviews that the reality show was an afterthought for narrative flavor while the main focus was writing a gay fake dating trope story, the book’s The Epik Trek is surprisingly quite compelling. For those familiar with the Amazing Race, The Epik Trek retains the international travel and location themed challenges of the show but axes the racing navigation elements. However, Winging It With You tweaks the formula to be even more modern and appropriate (or cringy depending on who you ask) with today’s obsession with social media including more fan voting, couples shorts/reels, selfie sessions, and generally just cranking up the reality show shenanigans to an 11. While the novel chooses to skip quite a few of Epik Trek’s challenges for the sake of narrative pacing and relevance, those that are portrayed on-page are quite varied and clever, particularly the first challenge in Vermont. Being that this is fictional and does not necessarily have to be realistic, there are one or two challenges that the Amazing Race would likely never attempt due to the safety and liability required, making the novel’s take on the concept more entertaining. The challenges are also cleverly designed to either force Asher and Theo to get to know each other better or highlight each other’s personal strengths.

While the reality show format and traveling add a lot of excitement and flavor to the book, the story is still mostly a character-focused romance one that lives and dies by Asher and Theo. Fortunately for me, I loved both of their characters, particularly their chemistry and the natural growth of their relationship (as you can guess by the author’s intention, it’s not a “will they” but a “when will they”). While at first glance Asher comes off as the nervously nerdy and lanky MMC vs Theo who is more charismatic, built and handsome, both have far more going on beneath the surface and its actually Asher who is more confident in who he is once Theo’s public face starts to fade. The two complement each other well and have good fun, cheeky banter for majority of the book.

Interestingly, while the story is written from both of their perspectives and most of the plot initially revolves around Asher’s unfortunate relationship with his ex-boyfriend Clint and their obligation to the Epik Trek, as the story progresses its Theo that has a considerably more complex character arc and feels like the intended soul of the story. Not only is his backstory more compelling and unique compared to Asher’s that feels more typical for the M/M romance genre, but his baggage and past experiences feel more personal and meaningful. This might be me reading too deeply into things, but given Chip Pon’s real-life background where he mentioned he was a photographer in the Air Force where he met his husband, it seems too much of a coincidence to ignore. While Chip is happily married, Theo’s baggage traced back to his discharge from the military and inner demons feel like the negative alternate universe of the author’s own life of “what could have been” had things gone south. The level of care and nuance taken with Theo’s unresolved history and his distant, yet vibrant family feels more real than the rest of the novel’s character work and is almost like a self-insert kind of inspiration that added a lot of substance where the novel needed it the most.

While generally breezy and casual to read, I will admit that I sometimes found myself losing interest during the first half of the book. While not necessarily due to anything being particularly wrong with it, the story was quite silly and the two main characters felt a little generic to me (Theo’s quick Spanish lingo added a lot of personality though compared to Asher’s distinguishing interest in STEM). And while what was seen of Epik Trek was a lot of fun, I felt like it took a while for the show’s production actually start and when it did, it was a little bit underwhelming at first. Part of that’s on me, expecting the race part of the Amazing Race (though it can’t be too close for copyright issues) and the book’s blurb mentions different modes of transportation which are only really used within certain challenges, not between locations or Asher/Theo navigating trips themselves as implied. The book is also very much a “just vibes” kind of read which is fine, but a bit low stakes for me personally.

I was pretty sure this was going to be a 3.0-3.5 rated book for most of my read but fortunately Chip Pons hit the gas and cranked up the narrative content substantially in the last twenty percent of the story. A last-minute dramatic plot twist near the end of Epik Trek pleasantly caught me by surprise and I loved everything that followed, particularly the exploration of Theo’s relationship with the rest of his family and how he finally addresses the burdens he kept trying to run away from which is a recurring theme. There were small signs and foreshadowing here and there of this late ambitious material, but I would’ve loved to have had more of it earlier or more spread out to balance the over-the-top silly shenanigans. In general, I feel like the story could’ve also been longer for more opportunities for Asher and Theo to get to know each other more or segue into the harder hitting last quarter. I’ve heard Chip’s earlier self-published debut novel You & I, Rewritten is more poignant and emotional, so perhaps that one will be a bit more of my cup of tea.

A love letter to readers of queer literature looking for all their favorite romance tropes but incorporated into a gay romance, Winging It With You has a lot of good laughs and heart. Comically silly, steamy when it wants to be (you can tell the sex scenes were written by a gay man), yet wholesome and sweet, this novel really is a great romance escapism read. While it’s not necessarily the most heartfelt or deep story, it’s one that will leave you smiling and long for your own hot pilot to randomly walk into your life. Notably, other than the adult bedroom content, the book’s writing style and tone is very clean and wholesome which is surprisingly uncommon for queer romcoms that often come off as crasser and trashier. Initially a bookstagrammer who made the jump to author, you can really feel that this book has everything Chip himself would’ve wanted as a reader in this cute romance novel, and understanding what readers is more than half the battle to a great romance story!