My Top 5 Near-Misses (aka heartbreaking creative failures)
Welcome to my June author newsletter!
Greetings from yr friendly neighborhood novelist.
Monthly writing tips, pop culture recs, and secret peeks into the publishing process. Let’s go!
Hi hi and happy summer, y’all!
Mamdani won (I love him, I’m obsessed), the sun is out, life is good!
I am IN IT right now with two kiddos — Lulu is five months, and we’re sleep training this week (pray for me). Rozie is three, so curious, SO smart (like, scarily?), so funny, so sweet. Yes, she’ll have a full meltdown if I don’t cut her peach the right way but then she’ll tell me she loves me apropos of nothing and all is well. My wife and I even snuck away for my fave lunch, the Artichoke Sandwich at Misipasta — grilled artichoke, sharp provolone, hot peppers, on a sesame roll. Heaven.
In my writing life, I’m celebrating (with a cheese plate and bubbles) finishing the second draft of my new book (yet to be announced, but it’ll drop next summer). It’s another ensemble romance, this time focused around two couples, all friends. One of the bigger notes I was working to address was upping the emotional stakes for each couple, as (to quote my ed letter) “each one [has] a central obstacle that could be resolved with just one honest adult conversation.” Even though I regularly teach avoiding this, welp, I’d gone and done it!
One of the challenges in romance is giving the couples a robust enough reason not to just get together after they first meet, but solvable enough for them to be together by the end. If the reason is too compelling (one or both are too mean/too different/already with someone else), readers may end up agreeing and thinking, “yeah, these two aren’t a fit” = romance fail. But if the stakes are too soft, the tension slackens, and it feels like everyone’s making a mountain out of a molehill. We want to avoid everything hinging on a minor misunderstanding (mistaking a lover’s sister for their secret girlfriend) or, in my case, the lack of one honest adult conversation that’d clear everything up.
As is common, I found the solution by delving deeper into what’d already been established versus adding on new ideas or back story. I looked at all four characters’ pasts, family structures, and blind spots, and found more emotional wounds I could dial up and make more painful for them. Ultimately, the aim is to make the internal obstacles/wounds the reason they can’t be together (i.e. I don’t believe in love) versus external obstacles (i.e. We live far apart) which can be solved through logistics (i.e. One of us moves).
Writers, when you get revision notes, try looking at what you already have to solve the problems. As is often in life, the solution may just be right in front of you.
The public-facing life of an author often celebrates wins…
Published books, buzzy launches, positive press, celebrity endorsements. We don’t tend to see the things that don’t work out. Here are five of mine—including the historical novel I spent 18 months on that was dropped in a single call, the A-list actress who ghosted, and the $100K film deal that vanished overnight.
5. Starts at Sunset
This one wrecked me. I’d developed Starts at Sunset, a vampire-meets-underground-music-scene TV show, out of a self-funded short film I wrote and directed in my twenties. I won a national pitching contest, signed with a major production company, collaborated with a top-tier showrunner—and then the original producer of the short, who I’d naïvely signed over the copyright to for $1, came for it. A legal nightmare followed. His asking price to buy the copyright back? $77,000. I was in my twenties, broke, and heartbroken. The project collapsed. My dream job dissolved. All I could do was weep—and start over.
4. Girls With Pep!
After selling my debut novel, The Regulars, I poured 18 months into writing a second: a lush, sapphic historical set in 1920s Hollywood inspired by silent film star Clara Bow. I researched obsessively, worked with a freelance editor, and delivered a polished final draft… to crickets. After weeks of radio silence, I was told the book would only work if set in the present day. When I pointed out it was historical fiction, so no, it was dead in the water—but could I come in next week to pitch some other ideas? I spent a weekend in bed. Then I put on lipstick, pitched two new ideas, and wrote The Bucket List, then It Had to Be You. Girls With Pep still lives in my heart, but it’ll never live on a shelf.
3. Writing a pilot for a famous actress
After The Bucket List came out, a popular actress I admired (yes, you'd know her) approached me to create a show for her. I was thrilled. We developed a magical, funny, heart-forward concept called The Fairy, and I wrote the full pilot on spec—pouring in weeks of work and high hopes. I sent it off. Her manager replied: “We’ll have notes… in a few months.” I never heard from them again. Not a no, not a rewrite—just a ghosting that quietly crushed me.
2. The Regulars TV
In 2017, after three self-funded trips to L.A., The Regulars was optioned for TV by E! I was over the moon. I partnered with an amazing showrunner (hi Gail!) and we spent months crafting a sharp, heartfelt pilot—rewriting it over and over to please the studio, producer, and network. Everyone said they loved it. And then, out of nowhere, the network changed direction. The mandate shifted. The calls stopped. Just like that, it was over.
1. $100,000 to write the It Had to Be You adaptation
This was a rough one. I was so close to securing a huge check to turn my first romcom, It Had to Be You, into a feature—enough money to actually change my life, and an opportunity that would’ve escalated my career. It was all tied up with some investors who needed to sell a feature at Tribeca, which was all meant to be a sure thing—and then the film didn’t sell, and the check disappeared. I was in L.A. at the time, staying with my wife and kid at a friend’s lovely house. I remember sobbing alone in the backyard, thinking, I’m never going to get it—the nice house, the big break. It’s just never going to happen for me. Pity party alert!
All of these near-misses weren’t because I screwed up—they happened because other people made choices that didn’t go in my favor. And I’m doing okay. No house yet, but I’m working toward it, and I’m still very lucky, given I have my health, my family, and the privilege to write for a living. And so we go the only way we can: onwards.
It’s baaaaa-aaack! My Romance Workshop is coming atcha Monday nights in September! If you’ve ever dreamed of writing and publishing a romance, or anything with a romance subplot or influence, I got you! I pour everything I’ve learned publishing seven books, three of them romcoms, into this class. It’s accessible, encouraging, and ultimately transformative. I know of classes from 2021 who are still a self-organized writing group! Find out more HERE. Spots are limited, save $25 by using code EARLY25, offer ends 7/6.
I’m reading A Sharp Endless Need by Marissa Crane
It’s a literary queer sports centered around an all-consuming if unnamed relationship between two closeted high school basketball players, Mac and Liv. Marissa is a master at evoking the beauty and brutality of both sport and desire. The writing is exquisitely rendered on the line level, never cheesy, always fresh and surprising. I’m not a huge sports fan generally, but this novel still welcomes me in, as I know passion, I know heartache, I know pain, I know love. Really well done.
I’m also rereading Obama’s memoir A Promised Land for the third time (it’s my ultimate comfort read); LOVED Camille Kellogg’s new queer romcom The Next Chapter (very fun and sexy!); and am excited to dive into Alison Cochrun’s newest, Every Step She Takes, in part inspired by the short story she wrote for Heartbeat!
I’m watching Your Friends and Neighbors on Apple TV
It’s smart, salacious and fun, but moreso, my good friend Danielle DiPaolo is the staff writer on this show! Danielle and I first met in NYC in 2009, and got into the improv scene together. She moved to L.A. to pursue her dreams of writing for TV…right before the pandemic hit. She preserved, stayed the course, worked hard, found a writers’ community, and now she’s writing for top shows. She’s a great example of how never giving up makes big dreams possible.
I’m performing at Generation Women at Joe’s Pub
I’ll be at NYC’s iconic Joe’s Pub on Tuesday July 15th, hosting Generation Women’s “The Sexy Summer Show”. Our annual celebration of all things sexy is always a good time. Buy live tix or livestream tix now!
That’s it for this month! If you’ve read this far, let me know by clicking the “like” button below. Chat with me in the comments—I reply to every message and I’d love to hear from you!
So appreciate you sharing all of these!
Loved this! Love all the behind the scenes transparency. Thank you so much for sharing. It makes all of us feel less alone. 💗