I had a chance to catch up with Mike and Jilly and talk about their new Choose Your Own Misery book Dating. For those that don’t know I’ve followed their Choose Your Own Misery books since the first one, Office. Its been a fun journey of ups and downs, mostly downs, from the all too familiar office setting and holiday nightmare. Now they’ve set their sites on the world of dating. Here is the interview, enjoy!
Ian: So you guys are building off the success of your original Choose Your Own Misery The Office Adventure and the follow up The Holidays, how did DATING become the third idea for the series?
Jilly: We’ve always used a couple metrics when choosing which topics are ripe for misery: universality, and sheer awfulness. I think dating hits both of those pretty nicely; half the people in relationships probably only stay in them to avoid this hellscape.
Ian: How have the other books helped contribute to DATING and what are some of the things you learned while writing them that helped with DATING?
Mike: The process for writing this book was basically the same as The Office and The Holidays with the huge exception that we had to open up to each other and talk about our sex lives, or lack thereof. Being a mild-mannered, generally repressed Canadian, that was a tall order.
Jilly: Luckily for Mike, working on multiple comedy projects together means we know each other PRETTY well now. The process was streamlined. The shame was… partially dealt with already.
Ian: One of my favorite aspects of both previous books are the awkwardly realistic scenarios, can we expect more of that from DATING?
Jilly: Definitely. I think with these books we like to take relatable moments, then heighten them way past the logical extreme. Everyone’s been on a bad date with someone they have zero chemistry with; not everyone has had that experience with a Steve Urkel impersonator. We’re taking the real-life pain, putting it on a pole at the end of our fingers, and spinning it as fast as it can go.
Mike: There’s a lot of morbid reality and awkward situations in this book; I’d argue, it’s the most awkward book yet. After all, we’re dealing with a subject that’s still somewhat taboo and uncomfortable to talk about.
Ian: Everyone has experienced some form of misery while dating, how much of this is from personal experience?
Mike: A lot; after all, dating in 2018 isn’t easy. When it comes to procuring a date, there’s never been as many options as there is now, which makes people that much more disposable.
Jilly: I think like both our previous books, the specifics aren’t particularly autobiographical, but the general principles underlying them are. For example, no, I’ve never shown up for a date and been dragged into a secret fight club. But I’ve definitely swiped right on someone who seemed like a fit, only to waste hours of my life talking about their passion for birding or whatever. The underlying misery is ALL real.
Ian: I think I would rather talk about birding than end up putting lotion in a basket but I totally understand what your saying.
Ian: Dating has always been fairly complex, at least for a dummy males like myself, how did you narrow down the complexities to focus on?
Jilly: I think with any topic this big, you have to try to narrow your focus to the things you think are most representative, or just offer the best opportunities or comedy. Figuring out what those elements were was a HUGE part of the early planning process for us.
Ian: Who is your target audience for Dating?
Mike: Anyone who has been on a date will get a kick out of this book. Honestly. I’m not just saying that in an obviously transparent attempt to to cast a wide net so that we can sell a lot of books. Honestly, I’m not….
Jilly: Seriously, though, the misery of dating is kind of universal. Dating apps might be very current, but enduring a personality-flattening meat market, meeting garbage people, and pretending you like them so you can avoid the existential dread of dying alone — that’s timeless.
Ian: For those that don’t know the entire story you guys had a long distance writing relationship for a while, has that changed and if not how have you been adapting?
Jilly: Actually, it’s even longer-distance now; I moved to LA in the fall, which has added a fun “more time zones to navigate” element to our online chats.
Mike: In my opinion, there’s basically no difference chatting over Skype with a person as compared being in the same room with a person; if anything, it’s better because I know where the frame cuts off, so if I want, I can chat in my underwear.
Jilly: He says ‘if’ like there’s any doubt that it’s ‘always.’
Ian: This is why I’m jealous of people that get to telecommute from home, I know they spend all day working in their boxers.
Ian: In our previous interview we spoke a little about the process of putting together a Choose Your Own Misery book, how has the process changed and have you become more efficient?
Mike: We’ve become a lot more efficient: we know how to use the organizing software Gliffy really well at this point; we know roughly have many levels of choices we need in order to get to our word count, etc. With us being really familiar with the process, I think it allowed us to focus on the writing, and as such, I think it’s our strongest book to date.
Jilly: Can I just say ‘seconded?’ Coz that.
Ian: Office captured the misery in knowing your about to be an office worker until you die, Holidays captured the anxiety of family and traveling, what sort of misery can we expect to see in Dating?
Mike: Sexual misery! Also, the misery of dying alone, rejection, and a hell of a lot of self-loathing.
Jilly: Also the misery of shitting your pants. But then, that specific misery appears in all our books.
Ian: This is book three of the Choose Your Own Series what’s next for the series?
Jilly: For now, we’ve put a hold on additional CHOOSE YOUR OWN MISERY books, but who knows — there’s a lot more misery in the world that we could take on.
Ian: Where can people get a hold of you?
Mike: @theonald on Twitter; though, I infrequently tweet, or at least, I tweet then quickly delete the tweet.
Jilly: I’m @jillygagnon on Twitter and Instagram, /JillyGagnonWriter on Facebook, usually more than willing to avoid work by dealing with work-adjacent social media conversations about farts and/or other topics of our very high-brow comedy.
Ian: Where can people get a hold of the books?
Jilly: Pretty much anywhere! If your local bookstore isn’t carrying it, ask them and they’ll order it in. Also, the internet is a thing.
