Modern Seinfeld founder presents: a how-NOT-to guide for your 20s and 30s

Josh Gondelman COURTESY
Josh Gondelman COURTESY

Most of us have people we keep around in our lives purely for their optimistic nature, like the friend who reassures you that it wasn’t a big deal when you scanned your girlfriend’s texts to see who she was talking to, or so what that you answered your phone during an important job interview?

Josh Gondelman, co-founder of the Modern Seinfeld Twitter account (which continues the antics of Jerry Seinfeld and the gang in the present year) and staff writer on Last Week with John Oliver, and writer Joe Berkowitz, however, actually give it to you straight with their new book: You Blew It!: An Awkward Look at the Many Ways in Which You’ve Already Ruined Your Life (Plume).

For a funny-man like Gondelman, someone who’s been lauded for his kindness over and over again, the book, at least from its title, offers a bleak and pessimistic view on life. Its actual content, however, proves to inspire more giggles than remorse.

“The premise of the book is, here’s how you ruin your life, so you should steer away from these things,” Gondelman explains to The CJN. “I don’t know if it’s necessarily satire, as it’s not a parody of anything, but just a silly book of advice disguised as non-advice with jokes. It’s simply jokes.”

It sure is. The best advice, says Gondelman, is non-advice. “Stay in relationships and at jobs long past they’re enjoyable and fulfilling because you’ll never know when your next meal is going to come from and you never know if you’ll find someone better,” he says. “Find something that works and stick with it as long as you can.”

You Blew It! has been aptly described as a how-not-to guide for your 20s and 30s. It was first conceived when Gondelman and Berkowitz had the idea for a fake pickup guide called Getting it Wet: The Nice Guys Guide to Tricking Women from Friend Zones to Bone Zones. A parody of pickup culture, Gondelman says much of it was “nonsense,” so they regrouped and came up with You Blew It, which they presented as their own version of an etiquette guide. It’s a “here’s how to ruin any situation” as opposed to a “here’s exactly what to do,” says Gondelman. “If you steer clear of this terrible behaviour, you’ll find the spectrum of appropriate behaviour.”

The book has an “underlying tone” that tells readers when things objectively feel good, you can still feel bad, and that’s OK. “Maybe you did this ridiculous thing and screwed up a job interview or Thanksgiving, but everything good can always go bad. The flip side is everything bad is a hair’s-breadth away from being good,” he says, adding, “in terms of etiquette, of course. Not medical diagnosis or criminal charges.”

As a purveyor of Jerry Seinfeld and Larry David-influenced content, Gondelman (who describes himself as an Elaine, except for on his bad days when he’s “definitely a George”) essentially has a PhD in Jewish comedy, as those who’ve been following Modern Seinfeld have known all along:

“The book is definitely located within the tradition of Jewish humour,” he says, “as it’s really fixated on specific things, and having specific, unwritten rules that are important, and wanting to codify those rules. That’s the best part about Seinfeld, taking an unwritten rule, putting a name on it and saying, ‘Look at this, this is what I’m talking about, you can’t be a closer talker’, or ‘there’s good naked and bad naked,’ and I think this book continues that tradition.”

He also notes an occasion during his Jewish upbringing that had a profound effect on his love for comedy. “I remember when I was 10, my grandfather received an award at his synagogue, I believe from Moshe Waldoks [co-author of the Big Book of Jewish Humour]. I fell over laughing, and read that book cover to cover. There was a lot of people you could look at in the tradition of Jewish humour and relate to, like, ‘That guy’s like me, we have similar sensibility, I relate to the things they’re saying.’ Like Mel Brooks, for example. He looks like someone I would know.”

While You Blew It! can, at times, be personal, as a stand-up comedian and social media star Gondelman’s all too accustomed to being exposed. “When you do stand-up and people don’t like it, you know they don’t like it since you’re in the room with them. So a book provides considerable more shelter and protection. I can just not read reviews. Very few people will actually reach out and say, ‘Hey, I read your book and I hated it, and you’re garbage,’ whereas when you’re on stage, you will feel the good will leaving the room.”

In addition to writing tweets for Modern Seinfeld, and working full time on Last Week with John Oliver, Gondelman is also out four to five times a week doing standup comedy, which to him isn’t even enough. “People who are in standup are easily doing 10 to 14 sets a week,” he says. “I know the ‘grass is greener’ on the other side of the fence, but I just want all the grass.”

However, it seems that Gondelman’s lawn is one that would invoke more envy, noting his good fortune at working alongside Oliver on the acclaimed HBO show. “Sometimes I’ll write the joke, and the way he’ll do it is a hundred times funnier than I imagined it,” he says. If you’re curious as to what jokes Gondelman had a hand in, look for those that involve rap music, apparently. “There’s a joke I did where the punchline was, “It would be as bad as if our nation’s middle school students were getting their sex-education from Lil Wayne.”

As for his favourite Seinfeld episode, it’s The Switch (where George and Jerry scheme a way for Jerry to date his current girlfriend’s roommate). “I remember seeing that episode as a young teen and thinking, ‘Yeah, that makes sense, that’s what adult life is probably like.”