Well, that season of the year is upon us once again.It’s March Madness. And that means one thing: It is time to pit arbitrarily selected things against each other until one of them emerges victorious!

I have already picked out some basketball-playing teams of tall youths as putative winners so that Warren Buffett can include me in the payout later, but surely, I thought, it would be more fun to watch a match-up between Things I Actually Knew About. Like, say, moments of Peak Awkwardness.

Life is full of these. Pushing doors marked “pull.” Waving at people who aren’t waving at you. People who try to talk to you in the restroom. Phone calls, full stop. But have we ever tried ranking them?

Thus, March Awkward Madness was born.

Out of the walking cringe-crucible that is our day-to-day existence in the Internet Age, I have isolated 64 solid contenders for Peak Awkward, including specific incidents and a few wild-card broad concepts. Which is more awkward: cats or tumblr? I look forward to finding out along with you. Vote early, vote often. I’ll update with the results of this round and the match-ups for the next one on Monday!