It’s ‘Wheels Up’ on Chip Pons’ Steamy New Romance ‘Winging It With You’

The following interview contains minor spoilers for ‘Winging It With You.’

When the idea for his novel Winging It With You first came to Chip Pons, it wasn’t just about crafting a swoon-worthy romcom. It was about building something much more important. Inspired by his and his husband’s favorite late-night comfort watch, a deep love of fake dating tropes, and, of course, Taylor Swift, the story took flight in more ways than one. What started as a fun, chaotic adventure on the page turned into one and the same for the Chip. After a successful self-published debut that transitioned him from Bookstragrammer to author, he decided to try writing a different genre. His exercise in leaning into happiness would set him on the path to traditional publishing and the opportunity to share his vision with a wider audience. Now, spurred on by what he calls a “dream team” of agents and editors, Chip is ready to show the world the value in showcasing and celebrating queer joy.

At its core, Winging It With You is for anyone who’s ever needed a second chance—whether it’s at love, at risk-taking, or at reimagining what your life could look like. Asher Bennett is setting out on the experience of a lifetime, unexpectedly single. Which is worse than it sounds because The Epic Trek is expecting him to participate with his boyfriend. Luckily for him, Theo Fernandez, a grounded pilot Asher meets at the airport lounge, has never been one to turn down an adventure. Through passport stamps, ridiculous challenges, and a fake relationship that gets harder and harder to let go off behind the scenes, Asher and Theo begin to realize that sometimes life lands you right where you need to be. Equal parts hilarious and heartfelt, Winging It With You is a romcom that celebrates falling in love in public and in private, but more importantly, it champions falling for the life you didn’t get to plan for.

Chip chatted with The FMC about the inspiration for his second book, what he likes best about traditional publishing, the importance of queer joy, and more.

Congratulations on Winging It With You! The first thing I need to know is: Would you personally go on an international competition show with a stranger?

Honestly, just to do it for the plot? I probably would. If that stranger was Theo Fernandez, hell yeah. No questions asked. [laughter]

What kind of show would you want it to be? Would you want it to be similar to The Amazing Race?

I would want it to be more like my fictionalized version: The Epic Trek. I would want to be on a show that was less reliant on navigating from place to place. I really enjoyed creating this world where both my main characters could be passenger princesses and get chauffeured around from one challenge to another. I would want to do something that's both physically and mentally challenging. Maybe a show similar to old school Fear Factor. 

Oh no. Absolutely not.

I know it’s gross, but if I'm gonna do it, I'm leaning into it. I'm going all in.

I love the instigating plot of this book. It felt fresh, at least to me. Where did the idea come from?

I knew when I self-published my first book that I wanted my second book to be something light and fun. My first book was the book I needed to write at the time. Was it the best book ever? No, but I was clearly working through something. It was all about grief, fathers and sons. I wanted whatever I wrote after to really embrace romcom as a genre. I knew immediately that fake dating was the trope that I wanted to explore. To me, there's nothing more fun than watching characters squirm and feel awkward when they're supposed to be showing affection and interacting with the person everyone thinks is their boyfriend, husband, wife, or whatever. 

It’s a classic for good reason.

It is. There can never be enough.  On top of that, for the past 12 years, my husband and I have literally fallen asleep every single night to the show American Dad. The Seth MacFarlane, raunchy, dumb little cartoon has become our comfort show. I don't know why. But, there's an episode of American Dad called ‘The Bitchin’ Race,’ and it’s a spoof of The Amazing Race. I was watching it and I was like, “You know what? This would be hilarious as a romcom.” The specific way they portrayed it in the show gave me the idea. One partner was super into it; the other was lackadaisical and couldn't care less about the competitions. The situation was made for two people pretending to date. It lets you put them in every single mode of transportation known to man, cram them in hotel rooms, cram them in airplane seats next to one another. It’s perfect. My brain went straight to: how could I torture these fake boys in the most public, draining and stressful way?

[laughter] How did you pick the locations and games when essentially the world was your oyster? 

I have a list of so many unused challenges. There were so many scenes that I started writing, but they would become too complicated. It was easier just to give up and try something else. For the show in general, I knew I wanted it to be travel-centric and something that gave Asher a true adventure. I wanted him to “come back to life” on this show. I knew I wanted to explore fears for both men, so I started there. I thought, “How funny would it be if the pilot was afraid of heights?” For Asher, I took inspiration from myself. I also have a deathly fear of snakes. That was two challenges decided. For the rest, I started Googling. 

[laughter] 

I would Google obscure facts and locations. The first challenge location came from a random internet find that I became obsessed with. Like you said, the world was my oyster, and I had a lot of fun letting my imagination run wild for a minute.

Speaking of letting your imagination run wild, how has this release differed from your Indie release that you mentioned?

Right now, I‘d say the biggest difference is the amount of control I have and the amount of support that I've received. I did everything for my first book by myself. I wrote it, edited it, picked a cover artist, designed the cover, did all the marketing, did all the planning, and did all the ARC distribution. It was a wonderful experience. I would do it again. In fact, Winging It With You was supposed to be self-published, and then I ended up getting an agent and going through the rewriting process with her, which led to the entire traditional process. I feel like I learned so much from this experience. It has been so lovely to have the support of my team. I could not have asked for a better one. My agent is my dream agent.

My editors are like these incomparable women who have taught me so much about the book space, romance and myself as a writer. I feel so lucky to have them holding my hand and rooting for me throughout this whole thing. It really has felt like a partnership. I started as a Bookstragrammer. I have self-published in the past. My traditional publishing journey so far has been a very validating experience. My team has leaned on me and recognized that I did something right the first time, completely on my own. To now get to do it alongside people that, one, I greatly admire and respect, and two, are trusted professionals in this industry, is exciting. I'm telling myself to appreciate and love every second.

Was the writing process itself any different once there were more people in the picture? 

Not really. I put a lot of pressure on myself to prove that I was good enough to be there, that I was worth the risk that everyone was taking on me. I was feeling all of this unnecessary pressure. No one was making me feel that way. It was all in my head. It was so lovely to be able to pick up the phone and call trusted people with years of experience in this industry if I was stuck or something wasn’t working. Honestly, the biggest surprise for me, and again, I want to reiterate that I have the dream team and recognize how lucky I am, because I know not everyone gets this lucky, was building that relationship of trust with my editor and to getting to work with people who value my vision and respect what I want the heart of my stories to be. For instance, when we were going through the final stages of editing this Winging It With You, my editor recommended that I end the book three chapters earlier. However, those final chapters were really important to me. I advocated to keep them and was truly heard and listened to. Queer joy is at the center of everything that I’ve tried to do and that I want to do and I am so thankful that I have people in my corner who understand that.

That's great to hear. I am. I will say, just so your editor knows, those last few chapters were my favorite chapters. They’re rare in romance books and so lovely to experience.

For me, it was really important, because in the LGBTQIA+ space, a lot of our stories are so rooted in trauma and in pain and people telling us when and where we can and cannot love. I really wanted that swoony romcom, big-romantic-gesture, blissful feeling of love to be on the page.

It’s definitely there, and I think it’s what makes the story shine as much as it does. The book is written in dual POV. Whose headspace did you enjoy writing from most, Theo or Asher?

When I started writing, I thought I was totally going to be team Asher. I thought getting into his head was going to be so easy for me. As I was brainstorming who he was, I was like, “Oh, I got this”. But then, Theo's POV ended up being so fun. I married into a big Spanish family, so sometimes it felt like I was writing from my husband's POV. I got to pick his brain a lot about his upbringing, and the way his family is so warm. I married into the best family ever and could probably talk about them forever. [laughter] When I was writing from Theo’s POV, it was nice to be inside the head of someone who was so warm. Sometimes he’s cocky, but he is genuinely a good guy. It was a fun headspace to be in. But all in all, writing dual POV is the worst thing that has ever happened to me.

You're contracted to write another book, is it dual POV?

It is. [laughter] So I did subject myself to it again. Dearly Departed, my next book, was the first I’d written entirely using the traditional process. So I wrote the big synopsis of the book, and then the first three chapters, and then Putnam, my publisher, bought the book and told me to go write it. This time, I got to work with my team from the start. I took what I learned from my Winging It With You rewrites and implemented those things into this draft. I heard my editor's voice in my head as I was writing. This was the first time I had consecutively written a book, from start to finish. I've never done that before. I usually write random scenes and stitch them all together at the end. This story was practically vomited onto the page from start to finish. I wrote it in a straight shot in less than a month. 

Oh, wow. Yeah, that's crazy. 

Yeah, it was an experience. 

Sometimes you just have to get everything out. Then, you have something to edit. People love to say a first draft doesn’t have to be good, it just has to be finished. 

Everyone is correct. Some people I know call their first draft their garbage draft.

For Winging It With You, what was the biggest change in the story from the first draft to the final edit?

When I first wrote the book, the whole plot was behind the scenes. There was not a single competition on the page. The reality show was originally only meant to be this thing that's happening around them. The only thing on the page was Theo and Asher in their forced proximity moments when the cameras stopped rolling. That was my vision for the book. Most of the time, when you watch these shows, all you see is what's happening on camera, so I thought it would be interesting to do the opposite. When I got an agent, she was like, “Love this. Let's add all the challenges. That's where you get the conflict. That's where you get the high stakes. That's where you get the drama. Your readers need to see that, versus being told that.” Her feedback made total sense. Again, this was such a growth experience for me. So, there was actually a huge change.  

What excites you most about the story not being just yours anymore?

I love that my book is in readers’ hands. With my first book, I was so nervous coming into the publishing space from being a bookstagrammer. I cherry-picked everyone that I sent an ARC to. I knew all my friends were going to love my book, so I literally only sent it to my friends. It was wonderful. This time around, I did not send it outside of my tiny little reader group. I didn't send it to anybody. All of the reviews that are coming in are from strangers and people who are finding the book on their own. You and I Rewritten was so personal to me, and I got to connect with readers on such a deep level. Now, it's fun to connect with readers on a much more low-key, thirst trap, funny, romcom vibe.

And you set the tone so well with the epitaph. I love an epitaph. Did you always know you wanted it to be a Taylor Swift lyric?

Oh, of course. Taylor is the guiding force in my life. When I’m thinking of book titles, chapter imagery or general inspiration, she's always where I go. She's the ultimate storyteller, in my opinion. The line I used, “grab your passport and my hand,” is so literal. Obviously, that's what Theo and Asher are doing–grabbing their passports and going on an adventure together–but I also felt it went hand in hand with my dedication, which is all about taking those leaps of faith and trusting that everything's going to work out. 

I love how much thought you put into it. Because that’s how much thought I put into interpreting them. Lastly, if you could write the story of your own life, if you had complete control, which trope would you include?

I mean, I would love a Hollywood romance. Sorry to my husband. But, could you imagine someone like Glen Powell wanting to be your boyfriend? Like, yes, Glen, absolutely. Whatever you want.

[laughter] I can imagine and I have imagined that exact scenario.

I’m dying to write a Hollywood Romance. I just think it would be so fun to immerse yourself in celebrity culture and what that means. It's the behind-the-scenes stuff with that trope that really gets me. The whole, “Oh, okay, like you're this to the public, but behind the scenes, you're a mess.”

Me, too. I love a Hollywood Romance. If you write one, let me know. I’ll pre-order it as soon as possible.