The Insta-dent

I poured myself a chilled glass of Stone I.P.A., then sat down to enjoy what would be a very anticlimactic World Series Game 7. During a commercial I pulled my phone out and saw a pair of missed calls. Spam, most likely. Then I looked closer: it was the number for Health & Science School, where I worked in Oregon for three years. A couple minutes later, and a text arrived from my former vice principal, Maria, asking me to call her. I figured she was having trouble finding boxes of score reports or test manuals I had buried in a closet before heading out the door.

“Hey Jack! So I just wanted to talk to you out of a professional courtesy…

This would not be the conversation I had anticipated.

Maria went on to explain that students were poking around on Instagram and managed to find my profile, and with it, a couple of enticing photos: one of my pale, naked chest and thighs I snapped before Portland’s annual Naked Bike Ride (don’t worry — I blurred out my cock!) and an unflattering vista of a nasty tanline acquired from one afternoon without sunscreen off the shores of Oahu. Maria used the phrases “rumor mill” and “circling around” and “confiscated her phone” and “they really like the ‘beach buns’ one,” so I can infer that a screenshot of my naked ass has made the rounds to all of my former students and colleagues. Attempting a graceful exit from this embarrassing conversation, I inquired if she had found all the boxes of test materials okay — great, great, that’s good — and hung up.

After an annoying student pulled up my Facebook page on his phone and showed it to me during an after-school tutoring session, I had upped the privacy game on my social media accounts and simply prayed that none of my students had the presence of mind to try the url “” (immediately after the Insta-dent, I went here and hid my lactation-forward animated short The Big Spill from the Internet). However, after saying goodbye to my life as a public educator this summer, I decided to go public with my Instagram — for no better reason than wanting more likes and followers. After speaking with Maria, I turned the switch back to “private.”

The difference between shame and embarrassment is sort of like the difference between poetry and film. Shame is sticky and internal, like poetry, while embarrassment is situational, even dramatic. I am not ashamed that some thirteen-year-old dorks in Oregon were enthralled by my digital ass for a week or so — I repeat, I am not ashamed! — but of course I am a bit embarrassed, and quite tickled. The tough thing about trying to make it as an internet comic these days is that your past as an instructional assistant will never disappear…it sticks to you like tar….

When I was a freshman at Langley High School, a photo of my English teacher went “viral” right around the end of the year. In the photo she is slightly bleary-eyed, clutching a bottle of beer; someone had found it on some murky pre-Tinder online dating portal, and being a dickheaded 15-year-old, printed out hundreds of copies of the pixelated image and pinned them all over her room before the last day of school (note that printing was the primary form of distribution — this was 2007). It was an incredibly mean prank — I remember peering through the little rectangular porthole in her classroom door during passing time and seeing her inside sitting at her desk, crestfallen. At the time I wanted to go in and say “I’m sorry this happened to you,” though I imagine being consoled by a 9th grader who looks like Buckley from King of the Hill would have only added insult to injury.


Me in 9th grade, and Buckley.
Me in 9th grade, and Buckley.

I do find it terrifying to think about the effect smart-devices will have on younger generations — and has already had. On more than one occasion at Health & Science I heard “my phone is my life” fall from the mouth of a middle schooler. Everyday at lunch whole tables of high schoolers would set Minecraft open before them on their state-subsidized Chromebooks, and spend the entire thirty minute block without saying a word (for the record, I spent many lunch periods at Langley in the library trying to wrap my head around novels like The Crying of Lot 49 and Naked Lunch, though I contend that this behavior is far more wholesome and adorable). Many kids claimed that they preferred to compose essays on their phones — and some teachers let them — but I didn’t tolerate that bullshit. I intercepted dozens of Snapchats as they were being snapped and chatted, most often depicting some kind of mild bullying — if there’s one app that I can say has unequivocally no positive effect on society, it’s Snapchat. Who knows how many terabytes of child pornography have been funneled through their servers in the past five years.

Obstinate kids will complain that it’s not fair to rob them of their smartphones because they can “multitask” and that they can learn so much more from the Internet than they can in the classroom. Sure, but being socially inept will forever be a pre-condition of being a teenager: when I showed up in a hoodie and jeans to watch some students play an indoor soccer game, one of them said to me, “Mr. Berkley…I didn’t realize… you dress like this outside of school…” Yes, David, sometimes I just like to kick it in some comfortable denim, and sometimes I might think its a good idea to have someone take a picture of my ass and share it with strangers — I’m only human, after all!

"The tough thing about trying to make it as an internet comic these days is that your past as an instructional assistant will never sticks to you like tar...."
“The tough thing about trying to make it as an internet comic these days is that your past as an instructional assistant will never disappear…it sticks to you like tar….”

Albeit embarrassing, it was a bit flattering to know I had become a middle school meme. Initially I felt rather vulnerable: will this little virtual wardrobe malfunction define my legacy in education after three years of…some hard work, a lot of joking with kids and even more time sitting around, idly checking my Outlook inbox? Well, probably, in the sense that from now on the easiest way to conjure my memory will be “Mr. Berkley, that guy whose ass we saw.” In addition to burying my animation, I also hid the Matt & Jack videos from my website (temporarily!) but all this retroactive censorship felt neither good nor right. I’m proud of all the content I’ve decided to share online over the years, so why should I get cagey all of a sudden just because some teenagers 3,000 miles away might find it and have a giggle?

Jokes aside, I do care about my reputation and the kind of impressions I’ve made on others in my professional life — I just hope there’s room in one personality to be perceived as both a caring mentor and a sometimes-raunchy creative type. Mingling outside on a beautiful Spring day after the Health & Science graduation, I had a short conversation with a junior named Noe whom I often played basketball with during lunch. I asked him about his summer plans and where he’s hoping to apply for college; he asked me about my upcoming road trip and life plans, then told me that he thinks he’ll see me again — as a successful stand-up comedian. Naturally I was taken aback: he said this before I had attempted any stand-up, or mentioned any aspirations of it to anyone. And he said it with that naive, giddy sense of promise only kids are capable of. But it stuck, for I had that conversation in mind when I first decided to get up on stage in Charlotte, and I think back to it when I need a reminder of what I liked about working in schools, and why I wanted to leave. In a word, it inspired me.

How embarrassing.


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