Confessing my sins.

Reflecting on who I was and why I changed.

This edition of Tangle contains offensive language.

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When I was a teenager, I was kind of an asshole.

I wasn’t just stupid, arrogant and rude in the way a lot of teenagers are: I sometimes got too drunk, I smoked pot, I got chased by police on mischief night, I skipped class, I talked back to my parents, I drove too fast, I thought older people were dumb, and at 16 I thought I knew everything about everything.

I also spoke like an ignorant fool.

Throughout my teenaged years, I regularly called things that I didn’t like “gay.” I also used words like “faggot” and “pussy,” and frequently sung along to rap songs and said “nigga” out loud, sometimes even addressing my white friends (and, occasionally my Black friends) that way as some sort of deranged attempt at camaraderie.

Many of my white Jewish friends actually referred to me as a “jigga,” a label I embraced. It was a play on what used to be, but is thankfully (as far as I know) a no longer common slang word: “Wigger” or “wigga,” which was supposed to describe a white person who was “trying to be Black.” I earned the label “jigga” amongst my mostly white friends in my mostly white school because I loved basketball and rap music and I was born in Hamilton, New Jersey, where I lived in a predominantly Black neighborhood until I was five.

Reading these words now, and especially typing them, makes my skin crawl. So much so that I won’t write them out again plainly for the rest of this piece. Admitting to the fact I used them with any regularity makes my blood pressure rise a few million points, and makes me deeply ashamed and uncomfortable, especially knowing how many of my friends or readers of this newsletter never knew that version of Isaac.

But pretending I didn’t, or that I was somehow smart enough or not-ignorant-enough to have not been one of those “problematic white boys” in my youth, would be an act of delusion so grand that it takes less effort to just accept the ugly truth of who I was than it does to build up a façade of innocence.

What’s perhaps most interesting about my use of this language was that it didn’t represent my “worldviews,” or whatever worldviews a 16-year-old is capable of.

My household was an extremely open, loving, empathetic and accepting one. My parents, who were not especially strict, would infrequently wield their parental powers in a punitive way. For my brothers and me, punishment of any tangible kind typically required police involvement, drug use, or some kind of low-level vandalism. Maybe the one exception to this general rule was if we were heard using language like this, or disrespecting anyone because of their race, sexual orientation, religious creed or status.

I had no conscious prejudice toward gay people. I had gay friends in high school and since getting to college and becoming a functional, not-asshole adult, am now surrounded by friends of all sexual orientations and gender identities whom I love dearly, unabashedly and with hardly any thought about who they love or what pronoun they use. At the risk of sounding like the old trope, throughout my childhood and to this day, one of my closest friends in the world has been a Black man. And I was living under the watch of a strong-willed mother who was deeply respected (and at times, feared) — which is to say that it was a bit silly for me to be slandering someone as “soft” or “puny” or “lame” by calling them a slang word for a vagina.

Obviously, I was not some pure, non-judgmental teenager with no biases about people of different races or statuses or orientations. Most teenagers are judgmental pricks, and I doubt I was any exception. It’s just to say that I was walking around without any real understanding of what my language communicated about me to others.

The reasons that I used these words varied, but it was predominantly for one reason only: because the kids around me used them, too. And the only people who scolded me for using them were my parents or other authority figures, people who — at that age — I was not keen on allowing to police my language.

I’ve been thinking a lot about this younger version of myself for two reasons.

One, because in the last few years I’ve gotten a couple of Facebook memories that have popped up from more than a decade ago where I’ve seen old public posts of mine as a teenager that vary in content from embarrassing to abhorrent.

Two, because I’ve simultaneously been watching the reputations and livelihoods of people get destroyed for the language they use — some of them for the language they used as teenagers; language that I used at that age, too.

There have been quite a few examples of this, but the one that got me thinking most acutely about it was the story of a Virginia cheerleader named Mimi Groves that was told in The New York Times.

The short version is that Groves, as a freshman in high school, posted a video of herself on Snapchat saying “I can drive, n—s!” after receiving her driver’s permit.

A classmate, an African-American boy named Jimmy Galligan, came across the video when they were both seniors in high school. Fed up after hearing the word so many times in school, he saved the video with the explicit intent of using it against her some day. A year or two later, when Groves got into the University of Tennessee and accomplished her dream of making the cheerleading team, he released the video and called on the university to punish her. A chorus of people online joined him, and eventually, the school revoked her spot on the cheer team and then kicked her out of the university altogether.

I am sympathetic to both of the characters in this story.

As a teenager, if I had obtained a video of a classmate I didn’t like saying the word “kike,” it’s totally possible I would have held onto it with the thought that one day, I’d like to hold that person accountable. And, had that classmate risen to a certain level of success, achievement or notoriety, I would not put it past myself and my loathing for anti-Semites to release the video as a way to bring judgment upon said classmate. All this is true despite the fact the word “kike” rightfully carries less negative weight to me than the n-word carries for many Black folks in America.

At the same time, I’m also sympathetic to the girl. I doubt she thought she was hurting anyone as a teenager when she made that video, and by all accounts, there was little else about her as an adult to suggest she had any racial animosity of any kind (the school seemed to be a breeding ground for this kind of language, though). In fact, Galligan was reminded of the video when, shortly before releasing it, he saw Groves post an urge on her Instagram to “protest, donate, sign a petition, rally, do something” in support of the Black Lives Matter movement. It had been about five years since she recorded the three-second Snapchat video.

But in today’s climate, even an evolution of that kind no longer carries as much weight as the original sin.

I remember distinctly one of the first times I ever called something “gay” in front of someone who both knew better and was able to bend my ear. I was 15. He was a friend of one of my older brothers, someone I thought was really cool, and when he heard me say it he looked at me with disgust and disappointment I had never encountered before: “How old are you, dude? 12?” he said. “Do you understand how fucking stupid you sound?”

I remember my face getting hot and my hands sweating and feeling this great sense of shame. I wasn’t 12 anymore, and he knew it, and he knew somewhere inside me that I knew better, too, and now I had said something that clearly offended this person that I liked. This wasn’t a parent or teacher — it was a peer, an older, cooler peer, and he seemed genuinely hurt before taking a few minutes to explain to me why me saying something like that was not funny or reflective of who he thought I was as a person.

These kinds of interventions — condemnations sandwiched between tough love and patient explanation — began happening to me around the time I was 15 or 16 until I entered college. Most often, they were delivered not by the marginalized kinds of people who may be tangibly impacted by my words, but by “allies” — typically straight white people who confronted me on behalf of gay people, people of color, or women to let me know that I was acting like an asshole and sounding like a bigot.

Those interventions had a huge impact on me. They taught me about the weight that language has, the pain it evokes, the rage it brings about and the justified judgment it invited from the people who heard me speak that way. They taught me how unrepresentative it was of what I actually felt. And, coupled with the experience of befriending a lot more non-white, non-straight people as I grew into a man, I slowly became much more aware of how important it was that I change my language.

Today, I wince at these words, and dozens of times throughout my adult life I’ve tried to pass on the same patient intervention to friends (and occasionally strangers) who I hear speaking the way I used to. In nearly every instance, the people who I confront are not bad or evil or harboring any kind of ill will — they’re usually just people like me: young, surrounded by that language and haven’t yet been called out for it in a meaningful way. Of course, plenty of Americans still use this language with the express intent of being hurtful, or bigoted, but I rarely encounter those people in my day-to-day.

By all accounts, this is how my generation evolved into the generation it is today — we are far more conscious of our language than our parents may have been, and much more invested in the way our language shapes the society around us. It began with giving a platform to and hearing from the people impacted by this language, and it turned into allies of those people helping enforce new societal norms. In most respects, I believe this is a very, very good thing. I also believe it takes a certain level of maturity to understand it and a lot of grace to live by the awareness we’ve gained.

What I keep getting stuck on about this moment is who I might be today had I not been given those paths to redemption; those opportunities to be taught, to be spoken to, and to listen. Who I may have turned out to be, say, if I had had the same fate as Mimi Groves.

We have all sorts of social science, data and real-world examples that tell us about how to win hearts and minds. We know that many of the most radical people in the U.S., on the right and the left, are lonely and isolated. We also know that radical groups, from anarchists on the left to the Proud Boys on the right, love to prey on people who have been ostracized by the center or mainstream.

And we seem to understand fairly well how to win people over who disagree with us. Telling those people that they are evil, gross, racist, sexist, homophobic, bad, or otherwise horrible is the last thing on the list that we are supposed to do. Likewise, currying favor with the “opposition” usually doesn’t involve destroying their careers or ensuring the destruction of their childhood dreams. On the contrary, that’s a good way to make an enemy, not a friend.

This is not, as it might sound, some commentary about cancel culture, or the left — at least not entirely. For starters, the right has a cancel culture of its own: it cancels people for kneeling during national anthems or donating to bail funds or protesting police violence or uttering critical words about America. Many on the right tried to “cancel” gay people in the military or Muslims in Congress. President Trump frequently implored his followers to abandon their support for television stations or brands that criticized him. Just this week, Rep. Adam Kinzinger — who voted to impeach Trump — shared a letter from his own family disowning him over his decision to disavow the president.

In other words: both sides use the coercive power of collective attack to destroy their opposition.

It’s also not a call for more grace or patience from marginalized people in America. Given the history of our country, asking Black people to be more forgiving for something like the use of the n-word, or gay people to lighten up about the f-word, is an absurd and offensive position to take. And I’m not doing that here.

Jimmy Galligan, the young African-American boy in The New York Times story, explained that he did what he did in part because he had tried so many times to report this kind of language to the people who were supposed to care (parents, teachers, administrators) and nobody ever did anything. I’m not going to sit here and lecture him about how cruel it was to do what he did, even if I think the punishment Groves received was far too much for her crime. The failure was, mostly, coming from the adults. 

All kinds of people in America have tolerated being denigrated and marginalized — by law, by language, by cultural norms — for decades. It’s not some ancient history, either. My own mother was barred from a high school dance for being a Jew. Many experience this cruelty every day; some are experiencing it right now.

Rather, I wonder more about the way our current reactions to these sins are worsening the predicament we’re in. At 18, had I been dogpiled by Twitter or the subject of a New York Times article for something I said when I was 14, my reaction would not have been acquiescence or understanding or empathy for those I had hurt. It would have been rage. I would have felt slighted, attacked, cornered, unfairly held to a standard nobody else is. What did you do when you were 14? What did you say? Is it representative of who you are now? Why aren’t recordings of your teenaged years plastered across the internet? I would have wondered why the most influential newspaper in the country was writing about a Snapchat video I had made before I could legally drive.

And if you’re working from this position, one where a 14-year-old deserves some space to say stupid, hurtful and even bigoted things without being written about in The New York Times or losing their college admission five years later, it begs an even more difficult question: When should we stop extending a level of grace or understanding to those who wish to repent? At 18 years old? At 25? At 45? Shouldn’t we always offer paths to redemption, opportunities to apologize and correct course?

I often write in this newsletter about the need for empathy-led politics, usually by asking my readers to consider the lives of low-wage workers, incarcerated individuals, undocumented immigrants, or rural Americans who have been abandoned by corporate America. But subscribing to that worldview is pointless if it doesn’t apply across the board — to the people burning down buildings in rage after George Floyd is killed, or to the people who fear immigration because the neighborhood they’ve lived in for 40 years is not what they remember from their childhood, or to the politicians who took an unsavory position when they were in college. And it certainly has to apply to people who use offensive language, especially when it’s clear their intent is not to harm anyone (and yes, intent should matter).

What’s difficult about all of this is that I don’t actually have a good, clean answer. This is usually the part of a story where I’d offer one. It’s unfair and enraging to ask for more patience from the people who have been asking and waiting to be treated equally for hundreds of years. It’s also unfair and enraging to live in a society that seems more interested in punishment and destruction than rehabilitation when it finds the day’s villain.

Stuck without an answer I can only tell you about me. I was once a kid who committed the kinds of sins that could have destroyed my career today, and I committed them not because I had hatred in my heart but because of ignorance — I simply didn’t understand the weight of what I was saying. The changes in me didn’t happen like a light switch and they certainly didn’t happen by being crushed under the weight of public shame and criticism.

They happened over time, with the patience of people who love me, or saw the good in me, and slowly transformed me into the kind of person who is both ashamed of the young man I sounded like and proud of the person I hope I’m becoming. But I know, with honest reflection, that I may not have gotten to this point had I been born 10 or 20 years later, and I certainly never would have gotten here had nobody invited me down a path where I could redeem myself.

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This is a personal essay from the newsletter Tangle, an independent, ad-free politics newsletter that summarizes the best arguments from the right and left on the issues of the day. If you enjoyed it, please consider subscribing: