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Trivia 101: How to influence friends and win trivia

Updated: Sep 12, 2020

If the last 12 years have taught me anything, it’s that winning is much preferable to losing. Sure, I remember running up the score at bars and restaurants and vanquishing upstart opponents in order to win beer and validate a lifetime of perusing encyclopedias. But it’s the losses that stand out. Take my second place finish on “Jeopardy!”. Or don’t. I hate thinking about it so much, but for some reason I can’t stop talking about it.

And I know not all of you feel the same way. To some, Trivia Night is a stress-free way to engage with some friends and down some 1/2-price appetizers. This is not your newsletter. This is for the reals. The people who show up an hour before the quiz starts, because they can’t imagine eating during the trivia or answering questions on an empty liver. The ones that bolt up to the host’s chair to challenge a murky or even flat-out incorrect question/answer combo. The team everyone hates, until the “Redeemable For 1 Pitcher of Beer” cards come out.

I know you all have questions, even though that’s my job. And I’ll answer the most burning one: Yes, there will be another Office-themed Trivia Night. I promise.

So follow along if you dare. In your inbox, you should expect a few things:

-Trivia Tips, small tidbits to put you over the top at your trivia nights

-Things Every Trivia Player Should Know, a finely-tuned base of knowledge is everything

-What I Learned This Week, trivia that I learned while punching up my quizzes

Without further gilding the lily…

Tip #1: Pick the right Trivia Night

Pandemmie or no pandemmie, there are myriad options for you and your squad to attend a trivia in your real or digital neighborhood. Which one should you choose? The dive bar down the street? The Irish Pub downtown? The independent bookstore you pretend to order your books from but really get from Amazon? The choice can be more difficult than remembering which member of The Black-Eyed Peas was the oldest (

Is the Trivia Night run by a third-party company like Geeks Who Drink or King Trivia? If that’s the case, the floor is pretty high for the quality of the quiz questions and the format. You can expect the questions to be tailored to a broad audience, and there to be an audio round that plays you pop songs run through an 8-bit filter or sung by Unorthodox Jukebox. If this is your thing, bon voyage.

Me? I’m more willing to risk it. Finding a venue that lets the host write their own question sets is a must. There’s just no replacing the relationship between the writer and the material. Would you go to staged reading where a moonlighting administrative assistant reads Salman Rushdie’s book? No. Gimme the Rushdie. The risk here is that host is bad, misguided or both. With no peer-editing or any filter to run the format through, the questions or the game itself can be borderline unintelligible. I remember attending a new trivia night in Santa Cruz that was hosted by a married couple in their 50s. The questions were bad, the answer submission involved little slips of paper and a weird “betting” system, and there was enough emotional baggage in their marriage to make everyone VERY uncomfortable. Pass.

But when it’s good, it’s so good. When the host has a equal grip on the material and the audience, it’s like a hot knife through butter. But that leads to another question: how do you pick the host?

That one’s easy. Find someone in your age range. There’s nothing worse than being a 28-year-old in the prime of Millennial-dom and showing up to a Boomer Quiz Night. No, I don’t know The Moody Blues are and I don’t particularly care. That can go in reverse as well. Bring someone in their mid-60s to a Grad Student haunt and get ready to hear things like “I don’t use the YouTubes” and “In my day a Fortnite was 14 days”. One of the only questions I ask my clients when they book a private event is “How old is everybody?”. Trust me, it’s supes embarrassing to ask the matriarch of the Accounting Department to name a movie in which Petey Pablo appears as himself (Drumline).

Matching up with their academic background is useful. History degree? There’s someone similarly afflicted hosting a quiz near you. Pop culture nut? Find yourself a bored GenX-er at the local dive. Boomer Quiz? Try your local English pub, and prepare for British Invasion bands you never knew spanned the Atlantic.

Take a chance. Find a place with good eats, cheap drinks, and a host that watched the same cartoons as you did. And for heaven’s sake, support independent trivia. It may be all we have left.

Things Every Trivia Player Should Know

-There are two world capitals named for US Presidents: Washington D.C and Monrovia, Liberia

-The maple leaf on the Canadian Flag has 11 points

-Gene Cernan was the last man to leave the Moon

-The title of Hemingway’s “For Whom the Bell Tolls” is taken from a line in the John Donne poem “No Man Is an Island”

What I Learned This Week

-In the pilot of Seinfeld, “Kramer” was known as “Kessler” because Larry David didn’t get permission from his real-life friend Kenny Kramer to use his name

-No one knows what happened to the passengers aboard the Mary Celeste

-The Thames is not the longest river in England, the River Severn is five miles longer

-Before she became an actor, Michelle Yeoh was a beauty queen in The Philippines

-The first woman elected to the UK Parliament — Constance Markiewicz was a member of Sinn Fein

-The myth of The Wandering Jew

-Julie Andrews won an Oscar for her first film role, Mary Poppins

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