Surprisingly, there’s not a whole lot going on in Boston’s South End on weeknights. The evening walks are great and if you’re looking for a nice dinner out, you’re in luck. But in terms of weekday night activities, the landscape is barren, with one exception: Wednesday night trivia at Cleary’s in Back Bay.

The venue is ideal – a nicer pub with some stick to the floors; the day of the week is perfect to break up workdays with some fun; and the competition is STIFF. Based on Cleary’s location, my buddy Matt and I are usually competing against Deloitte accountants, Bain & Co consultants, graduate students, and other high-end trivia connoisseurs. Not only that, but under Pub Quiz Liz’s rules (Pub Quiz Liz pictured below), there is no limit to the number of team members for each team. So more often than not, Matt and I are competing against a gaggle of 6+ professionals. Our results reflected this disadvantage as we never finished higher than 4th out of 12 – 16 teams, often finishing towards the bottom. That is, of course, until one faithful night, with a last-minute partner switch, and a progression of questions woven out of the fabric of our deeply complicated lives.

Another buddy of mine, Zach, was in town before flying off to Montreal in the morning. I was excited, because this seemed like the perfect opportunity to add a third brain to the mix, but of course Matt had prior engagements that evening. We eventually found ourselves in 4th out of 16 with the final question, our largest point wager remaining prior to the bonus round where you wager a percentage of your aggregate points scored. I forgot the phrasing of the question, but it was something along the lines of a pop culture ‘icon’ born in the 1920’s with a hit reality TV show between 2010 – 2020. Zach was dumbfounded, but I on the other hand was brought back to painful nights on the family couch and my mom and sister’s obsession with Betty White & her show ‘Off Their Rockers’. Though I despised the show, we answered correctly and gained some ground before the bonus round.

Given that we were in the running for first, we decided to bet the farm on the bonus question, wagering 100% of our accrued points. As we eyed up the other teams to try to get a sense of how they’d wager, the question was posed around the name of the fictional female bounty hunter character from a popular series of novels in the 90’s & 2000’s. From the get-go I was useless – no idea at all. However, Zach’s eyes essentially went to the back of his head as he relived his family trips to the Cape in the summer, more specifically, his mother’s summer reading list. “Bright covers, bright covers, bright covers” he kept saying as if I had a clue to his reference. He was in agony as the character’s name was on the tip of his tongue, until he blurted out “Plum!” Though he couldn’t recall the first name, he was confident the character’s last name was Plum. Without knowing the first name, we prayed Pub Quiz Liz would accept the formal Jeopardy last name submission as we gave our last response.

After answers were tallied, Pub Quiz Liz did her normal spiel thanking everyone for coming out and announced the final results. As she read from last place to first with our names being excluded, we became even more excited. 3rd place: not us. 2nd place: NOT US and by that point we started jumping up and down and celebrating as if we had won the Super Bowl. We were given a king’s ransom for winning: a $50 gift card to Cleary’s and snapped a quick picture to hang on our fridge. As any competitor would do when they realize they won’t win again – we formally retired to end on top.

If you find yourself around the Back Bay area on a Wednesday evening, I strongly encourage you to try your hand in trivia and enjoy a burger & beer – you won’t regret it!

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By Thomas Schulte CFP® Financial Planner Read More