Then I thought, what if you could put more than one question for each entry, if you had more than one? I think a picture of video that evokes 10 different questions from some people would be just as perplexing as one that evokes 1 question from most people, if not more so.

I feel like the current measure isn’t a measure of perplexity, but clarity. I can clearly see what’s going on easily, and so I can ask a question easily, and move on. I’ve definitely had examples where I can think of a question and so I put one in, but I don’t think the image is that great (so I could also have said “I’m bored.) But if something is perplexing, it should be grabbing in a different way.

Some of the pictures are interesting, but my first question isn’t a math question. If I used this in the context of a math classroom, I could expect a bit of that bias, but I think part of the perplexity is that it shouldn’t be forced. So I’m going with non math questions for those prompts I find not boring, but also not math perplexing.

That’s great. The site doesn’t specify “the first mathematical question that comes to mind” or “the first academic question that comes to mind.” (I hip-checked Colin Graham about this early on.) To insist on either of those qualifications would be to admit that the tools of mathematical analysis are only useful for answering questions that arise in math classrooms, when in fact our tools have broad appeal. “How many pennies are there?” is a question that the woman on the street might have. We can help her there.

Seems the biggest winners are the area/volume/scaling problems. Proportions and unit conversions come next. I like your idea of tagging by standards, but don’t know if that’s enough incentive for people to fill in the holes.

I think you’ve identified the popular candidates. (Though if I see another photo with a lot of little things in it, I swear …. ) The purpose of tagging won’t be to drive people to fill the gaps between them, though. The design of the site lends itself best to applied math (which means polynomials and rational expressions will be scarce) and even then only applied math questions that arise in response to visual stimuli (which means a lot of statistical questions won’t show up). I’m still trying to figure out the jurisdiction of the site (what it’s good for, when, and for which people) but it may be rather narrow.

– The site looks awesome. Great design. On a big screen. I tried browsing it on my phone, and it choked on the videos. I apologize to those people for the Skips.

– Some of the pictures are interesting, but my first question isn’t a math question. If I used this in the context of a math classroom, I could expect a bit of that bias, but I think part of the perplexity is that it shouldn’t be forced. So I’m going with non math questions for those prompts I find not boring, but also not math perplexing.

– Seems the biggest winners are the area/volume/scaling problems. Proportions and unit conversions come next. I like your idea of tagging by standards, but don’t know if that’s enough incentive for people to fill in the holes.

Thanks for all of your great work.

2. An observation: I shared the site with my wife who is not a math educator. She as well was intrigued by what might come up next as she went from image to image. However as I was silently looking over her shoulder I noticed something. There were some images/videos that she was presented with that I also had responded to. Many of them very quickly invoked a question for me as my mind immediately started thinking about bounds and estimates, but I noticed that those questions did not come to her. For many of them she either clicked the bored button or had a question that was worlds apart from mine.
I’m now wondering when I look at the perplexity whether they are perplexing to math teachers or a representative sample of the public which my math classes are more likely to be. Data on who (Math intesive profession, Other) responds to the images might make the difference when trying to predict success and flop in the classroom.

3. I love the site and the value of its content.

That’s right. Interesting has a positive spin and is the first step into delving into the act of problem solving. Frankly, I don’t like being perplexed because I usually associate it with frustration as in this definition:

Perplexing:
1. (of something complicated or unaccountable) Cause (someone) to feel completely baffled.
2. Complicate or confuse (a matter).

I understand what you after with this, but I don’t think you are going to get a lot of takers for this outside of your current audience and without your personal explanation. Maybe another less perplexing word for this?