From the first bar Whaddayaknow? founder Daniel Burns decided to bring his style of trivia to the Chicagoland area in 2007 to the 100+ hosts currently entertaining knowledgeable social butterflies, our staff has hosted tens of thousands of trivia events, and have loved watching an awesome community grow, complete with countless, wonderful interactions with our valued event attendees!
But we’ve also seen some stranger-than-fiction stories that are almost impossible to believe. Here are some of the craziest true stories submitted by our Whaddayaknow? Trivia hosts.
Trivia Can Be a Contact Sport
No, we’re not talking about fights breaking out during a trivia event - the worst you’ll see is some mild bickering among teammates along the lines of, “See, Steve? I told you the answer was Argentina!” But if you think you can stay safe at an event where you mostly sit down, don’t be so fast. Our host “Eric” (we’re using aliases to protect our hosts’ identities, but you can scroll through our roster of hosts to see if you can figure out who told the story here) discovered that during a fundraiser.
I was hosting a huge benefit at The Bottom Lounge. There were easily 150 people playing, and there was an open bar. Apparently by the time we finished our ID bonus round, one of the patrons standing at the bar should have probably taken a seat instead.
From the elevated DJ booth I was hosting, I look over to see a small commotion and a man passed out on the ground! Apparently he had fainted, and only a few people around him even noticed. As they checked on him (he immediately woke up, and was okay) I had to debate between drawing attention to our rowdy guest, or figuring he had suffered enough.
I decided against calling him out, and I think he appreciated that.
When We Ask You To Return Your Pens, We Mean the Ones You Wrote With
This is a quick one that probably has happened to more than one host from “Emily.”
I asked a table, “Can I have your pens please?” A drunk woman handed me her vape pen...
How Everything Can Go Wrong…And Can Still Work Out!
Sometimes, things don’t always go to plan. And sometimes, that might happen when a host is training a future Whaddayaknow? Host (and Jeopardy winner). “Eliot” knows a thing or two about that.
I train a lot of our hosts (if you’re interested, we’re always looking for more!) and typically they come away knowing how a normal night goes, but also knowing that anything can happen, and that that is okay!
I didn’t realize I was going to show how EVERYTHING can happen, and how it’s still okay.
On a busy day, I rushed out the door for my trivia event where I was to train a new host. He told me he had won Jeopardy six times, and that I was allowed to share that with the crowd to pump them up. As I was setting up, I realized something. Something terrible.
I had forgotten my set.
“It’s okay,” I told our trainee (who is now one of our top hosts). “Most bars have printers in the back, we can print out the set.” It was a good lesson, since most hosts don’t know that’s an option if needed. So I connected to the bar’s wireless printer, and we were good to go.
Until the printer ran out of ink after 3 pages.
We have the ability to look up all the questions and answers as Whaddayaknow? hosts through our scoring website, but the bonus rounds require actual written clues.
So as we hosted, the two of us wrote down every single bonus question on blank paper. For 20 teams. We both had hand cramps by the end, but we got it done.
When we finished, just 10 minutes later than usual, we were both out of breath and exhausted. And not a single team even mentioned the change in the bonus rounds. I told the trainee, “Well, you’re never going to have as hard of a night as this. And look how everyone still left happy.” Hopefully it was a good final lesson for him to learn as a host.
Why Having Your Own Sound Source Can Lead to Special Moments
One of the offerings a good team trivia company provides is a sound source to play music between questions. Some of our hosts even like to make their own curated playlists that leave subtle hints to any keen-eared players. This also means we can pivot and pull up a song to celebrate an important occasion, like our super-host “Jack”.
At Chuck’s Southern Comforts Cafe in Burbank, which hold’s trivia each Wednesday at 7:30 p.m., there were three teams of “regulars” who show up just about every week.
One was “We Brought Our Mom” - a team that always brought one of the teammate’s mothers along to play.
I always liked it when that team played, but there was a period where they weren’t able to make it out on Wednesdays. So after a bit of an absence, I was thrilled when they showed up, only this time under the name “We Brought Our Mom Back.”
They won by ONE point, and I scrambled with his audio source and played, “Mama Says Knock You Out” in the background while announcing the winning score.
When a Good Date Turns Into a Bad Date Turns Into a Free Drink
Team trivia can be a great way to break the ice on a first date. Sure, some might be intimidated - we’ve seen many duo teams where one or both feel like they’ll embarrass themselves by getting questions wrong. But really, it’s a low-stress way to compete as a team and get to know each other between questions in a fun, casual setting.
In this case, our host “Andrew” saw the allure of trivia as a date first hand…until it ended.
I was hosting at a very nice cocktail bar that ran trivia on Sundays. Think, dark wood, low lighting, high-end drinks. This isn’t a place you order a shot of malort. Instead, they poured “ferraris” - a mix of fernet and campari. We had a few regulars, but most weeks we had at least three couples on first dates playing along.
Up until the final round, one couple sitting at the bar were crushing it. They were comfortably in first place, and on their way to a great gift certificate prize. And then…well let’s just say the date started going well.
The pair didn’t turn in any answers for the final round because, well, they were very publicly and not at all discretely displaying quite a bit of affection. I didn’t want to intervene because, well, awkward, so I continued with the final round, watching their nightly rankings drop in the process.
Right as I read the final answer to the final question, the woman at the bar stopped making out with her date and, without a word, stood up and walked out of the bar.
The man remaining still ended up in third place, which was a free round of shots. I took one with him in solidarity.
No, The Host Will NOT Propose For You in Four Minutes.
Over the years, Whaddayaknow? has seen a lot of budding relationships from couples who met or bonded over weeks and months and years playing trivia together (or against each other). We’ve hosted dozens, if not hundreds, of wedding events for our regulars, from wedding parties to bachelor and bachelorette parties and more. We’ve even had hosts officiate, and at one massive Tournament of Champions we even had a proposal.
We’re happy to facilitate such romantic gestures at our events, but… it’s best that you ask us first (contact us here if you want us to set up any fun surprises or events). Otherwise, you’ll have an experience like “Carmen” had.
I was hosting a very busy night at a very crowded bar in Wrigleyville - the kind of spot most 20-somethings go to after Cubs games. There were over 30 teams, and the venue needed the game to be finished in 1.5 hours for a scheduled event.
Now, typically we finish our games in around two hours, and anything over 15 teams is considered a busy night, so needless to say when someone came to me just FOUR MINUTES before our start time asking me to help him propose to his girlfriend, that was a hard pass from me.
I thought to myself, “Sir, first of all…you want to get engaged in WRIGLEYVILLE?” I love the venue, but it’s not exactly the most romantic place. I didn’t say that, of course, I just said I didn’t have the time to help plan a sudden proposal, and told him to keep it simple and just ask her to marry him.
And it turned out, he didn’t even want to play trivia! Apparently, she said yes, but shortly after the proposal a server spilled a drink all over the man’s shirt. Hopefully they had taken their engagement photos already.
Anything Can Happen at a Whaddayaknow? Trivia Event
This is just a sample of stories our hosts have experienced, but every night is a chance for a unique, fun, hilarious and, occasionally, embarrassing story of your own. Over 17+ years of events in a city that is absolutely the perfect soulmate for us, an amazing community has blossomed encompassing the widest range of people, and for that we could not be more grateful!
Check out our locations for an event near you, and contact us any time for a tailored trivia game for your own event of ANY type! And of course, we’re always looking for new hosts, so contact us if you would like to join the team!
