Whether it’s Jeopardy!, bar trivia, HQ Trivia, or Trivial Pursuit, I love a good test of knowledge among friends. And while I understand that being good at trivia doesn’t necessarily line up with intelligence—being able to quickly regurgitate facts doesn’t mean you can solve complex problems or have any amount of emotional intelligence—boy, does it make me feel real stupid when I get trivia questions wrong.

Which is why my participation in LearnedLeague, an online trivia league that’s been running since 1997, is an exercise in pure masochism. In my very first season as a LearnedLeague rookie this summer, I answered just 35% of questions correctly, compared to the rookie league average of 47%.

I’d read about LearnedLeague a few years ago and was immediately interested, but because the league is invite-only, I had to shrug my shoulders and move on. When my friend David mentioned an online trivia league in passing, I knew that I’d found my in.

I wasn’t expecting to do particularly well—I’m a middling bar trivia competitor at best—but I somehow came in 17th out of 30 rookies. How was I able to pull this off despite answering more than two-thirds of questions incorrectly? Well, getting answers correct is not how you actually win at LearnedLeague. Each LearnedLeague season takes place over 25 days. Every day, players are matched up with one other person from their rundle—essentially a division of players based on their skill level. Everyone is given the same six questions to answer. Answer them correctly, and you will gain points.

Here’s the twist: the point value of each question is assigned by your opponent, who can see exactly how well you’ve done at answering every single question you’ve ever been posed in your LearnedLeague history. This history is summarized by question category on the match page—for example, you’d be able to see that I have gotten 67% of questions about television correct, but only 20% of American history questions, a statistic that would horrify my high school teachers.

The trick is to try and guess which questions your opponent is most likely to get right so that you can assign them the least amount of points. With good defensive scoring, it’s possible to win matches even if you don’t get the most questions correct. Of course, your opponent can always surprise you—if I ever get a question about classical music correct, it’ll blow my opponent’s mind.

Each match is designed to be a test of your knowledge, recall, or ability to guess at that exact moment in time. That’s one reason why LearnedLeague’s founder Shayne Bushfield (or Thorsten A. Integrity, as he goes on the site) tries to write questions that feature multiple paths to the right answer. Take this question from last season, for example:

Illyria is the setting for what Shakespeare comedy, which ends with Olivia betrothed to Sebastian, Orsino announcing that he will marry Viola, and self-righteous Malvolio taking a powder? The play is believed to have been written for entertainment on the Feast of the Epiphany (hence the name).

Any of these clues could be the basis of the question on its own, but with the plethora of hints available here, players could come to the right answer (Twelfth Night) in a variety of ways.

Of course, some questions are cloying and too clever for their own good, and you’ll find plenty of complaints on the user message board to that effect each morning after the results have been released. I do a less public version of this—I text David when I find a question particularly irksome.

Despite my subpar performance, I immediately paid a year’s membership dues upon the conclusion of my free rookie season. What can I say—I’m a sucker for stats, and building up a full archive of questions and answers is half the fun. And while it is humbling to get so many questions wrong, it just makes it all that much sweeter when I actually get one right.

Night Water

I thought I was smart. Then I joined…