Choose Your Own ‘80s Nostalgia

If you were a kid in the 1980s, you probably have two feelings about those Choose Your Own Adventure books: that they were awesome, and that it’s a shame they aren’t around anymore. It’s true, they aren’t. But authors Jilly Gagnon and Mike MacDonald have created something better - a choose your own adventure series aimed at those of us who loved those books, but now have inconvenient things like jobs and love lives to deal with. Choose Your Own Misery: Dating is the third in a series that also covers The Office and The Holidays, and simultaneously hits all the nostalgia feels and all of our modern social anxieties. We sat down with Jilly Gagnon to talk good ideas and bad dates.

With Choose Your Own Misery, you’re reviving a beloved ‘80s series. Those are big shoes to fill. Did you feel a particular pressure to live up to the expectations of our collective childhood nostalgia?
I think we definitely felt that pressure, especially with the first book in the series, Choose Your Own Misery: The Office. I mean, we're taking this thing that literally millions of kids loved, and making it dark and cynical and very much adult - we needed to nail the formula for what made those books so fun.

For us, it was that sense of the story twisting and turning in new ways every time you read it. The biggest challenge was making sure there was enough variety for readers.

How did you and Mike decide to take on these projects together?
Mike and I have actually been writing comedy together since 2011 - it started with The Smew, a Canadian answer to The Onion (which is sadly now defunct), then continued with script ideas, book ideas, and the like. We would meet regularly and pitch each other new ideas that we thought might have legs. One day Mike pitched the idea of a choose-your-path book set in an office, where things start bad and can only get worse, and I loved it. That became the first book in the series, CYOM: The Office.

We figure out topics by wracking our brains for experiences that are very universal, but seriously prone to misery. Once you start applying that lens, The Holidays and Dating (books two and three in the series) felt inevitable.

I particularly appreciate that the female lead in this book has an empowered voice and gives zero Fs about what other people think of her. She’s bold in her decisions and is in total control of her dating life. What went into creating her?
When Mike and I started writing, we had some long discussions about what we wanted the book to do. In all our books, the characters you play as are pretty terrible, but the goal is for that, and the comedy that arises from it, to illuminate problems in the world, not reinforce them. We wanted her to be a lens onto some of the worst aspects of the dating world for women, and having her be sex-positive and seemingly in control made those moments land harder for us, both as jokes and in service of some of the larger, sometimes upsetting themes we wanted to highlight.

There are some moments in this book that are so funny but that really make you cringe. Wound sex comes to mind. Did you two just sit together and brainstorm about the most horrible things you could think of for dating scenarios?
Not exactly... but we're always looking to heighten the situation for readers, and make a familiar experience bigger and funnier than it would be in real life. I mean... everyone's had unsatisfying hookups, but the wound sex version is (hopefully) pretty Next Level Awful.

What’s your favorite narrative line in this book?
I'm personally super partial to the track where you wind up starting a new career as a Kathy Griffin impersonator because of a fateful right-swipe. Though the underground right club for norms is also pretty great...

How much of this is based on real life? Yours or other peoples'?
Oh man, I feel like admitting that could seriously damage my reputation. Honestly, most of the crazier scenarios are totally made-up - my real life just isn't that wild - but the desires and compromises and self-justifications that drive the characters' decisions were definitely experiences both Mike and I had.

Can you give us a dating horror story of your own?
Once, back in college, I decided I wanted to hookup with this hot guy I'd known since freshman year, so I took him back to my room...

...then changed my mind about the hookup. But this was WAAAAY pre-MeToo, so I didn't know how to just say that. Instead I went to the bathroom and made myself vomit in an attempt to make him want to leave. Which he didn't notice, so I did it again. He still didn't notice. Finally I just had to ask him to go.

Yeah, I know. There's a lesson there.

Choose Your Own Misery: Dating is available on Amazon.