The Reddit Connection That Got Me Into College

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I met him online. He texted me on Christmas. Two weeks later, we met in person at a Barnes & Noble.

This is the story of an internet connection that has nothing to do with romance. At 22, I was lost and living at home. I wasn’t looking for a date. I was trying to ace the SATs.

It was 2011 and I had recently dropped out of a Maryland rabbinical seminary and moved back into my parents’ house in Brooklyn. Although I was back in the community I grew up in, I felt different from everyone I knew. I was depressed and friendless. The internet provided solace and distraction, a community of fellow lonely people. I was particularly drawn to Reddit, which is essentially a mix of popular, crowdsourced links and conversations. The site has everything, from photos of the cutest kittens to long posts by NASA engineers about designing vehicles for the International Space Station.

One day I came across a post that caught my eye: “IAmA SAT/ACT tutor at the top end of the market in Manhattan. AMA.” AMA, in Reddit-speak, means “Ask Me Anything.” This generous citizen was answering questions in real-time about how he tutored the best and brightest of the Manhattan prep crowd. He framed the SAT not as a test of knowledge but of “college readiness,” and wrote about his strategies for, say, making “Beowulf” relatable to a high schooler. He charged almost 300 dollars an hour, but he got results: Some students added over 700 points to their exams. I was fascinated. Here was someone who held the logical keys to a foreign world I aspired to succeed in: college.

I grew up in an Orthodox Jewish community going to a Yeshiva high school where we got three hours of secular studies each day. Most of our teachers were never formally trained and some were community members who were between jobs. After grade school, I went to seminary both for self-edification and because it was what was expected of me. It’s not that college was ever off-limits. I just had no idea how to get there.

But peering into the world of this competent stranger on Reddit, I was overwhelmed by a mix of desperation and hope. I sent him a private message and asked for an hour of his time, but I was upfront about the fact that I couldn’t pay. I knew it was a really long shot — his time was clearly very valuable — and I didn’t expect him to respond.

But on Reddit, sometimes magical things happen. Although the community is a disparate group of millions of users all around the world and there are plenty of trolls, the website fosters real human connections between strangers. I once received a hand knit scarf and a random assortment of local beer from a Secret Santa whom I never met. Another time, when I expressed interest in astronomy on another conversation thread, someone sent me science textbooks.

So, hoping for the best, I reached out to the SAT tutor, and a few days later he texted me back, introduced himself as James, and we made an appointment to meet.

On a clammy and cloudy Tuesday that December, I found James in the stacks of Barnes & Noble, wearing fancy boots, jeans and a plaid shirt. He was tall, confident and extremely articulate.

“So, why did you drop out of rabbinical school? Crisis of faith?” he joked.

I told James that I was completely lost about how to get to college. My younger sister, a first-year student at the University of Chicago at the time, was an inspiration, but I had seen how hard she worked to get there, studying for her SATs since the seventh grade, diligently reading daily emails from the College Board with prep questions.

At 22, one glance at the college essay prompts would plunge me immediately into self-doubt. But I passionately wanted to go to school, to foster a curiosity that could not be sated with Talmud. I imagined being mentored by men in tweed jackets sitting in oversize armchairs, our faces illuminated by a crackling fire.

And James was supportive of that (although possibly amused by my vision of college). He spent hours with me that day demystifying the test-taking and application process and sharing study tools that I still find useful. He taught me the tricks to multiple-choice, and how to strategically answer math questions that I didn’t recognize. He walked me through my difficulties with subject-verb agreements and showed me how to “hack” large passages of text in order to answer reading comprehension questions.

At one point, we moved our study session to a nearby diner and James talked while I furiously scribbled notes in the back of an old SAT book with yellowing pages. He told me a little bit about himself: He had gone to the fancy prep school where “Dead Poets Society” was filmed and had taken four years of Latin there.

At one point, through bites of bacon and eggs, he started speaking in a strange dialect.

“What are you saying?” I asked when he stopped for breath and another slice of bacon. I was never that close to bacon, and it was distracting: It smelled like pastrami but was a little off, like being on a blind date with someone who is charming and likable but there’s no romantic spark.

“That’s Chaucer. ‘Canterbury Tales,’” he said. “We had to memorize it in high school.”

Through our conversation, I felt James’s confidence rub off on me and my fear of failure dissipate. I sat higher in my chair. When I went to pay for the breakfast, however, my credit card was declined and I was mortified. A perfect stranger had given me hours of his professional time — free — and I couldn’t even pay for breakfast. But he brushed it off, as if it was a nonissue.

For the next two months, I studied incredibly hard. I’d spend long afternoons and evenings at Starbucks, doing practice tests in a zombielike state. The night before the SAT, James sent me a good luck text and reminded me to eat a light breakfast, and bring snacks, a clock and extra pencils. I don’t remember much of that day. I hit the ground running and didn’t think. Eight weeks later, I received my score. I had jumped 400 points from my original test, and my writing section was in the 95th percentile.

I thanked him profusely, but didn’t see James again for another four years or so. By that point, I was a senior at Hunter College, pursuing a degree in history and minors in linguistics and English. My research on Yeshivish, a dialectical English spoken among sections of Orthodox Jews, had won an award at a conference and I wanted to tell James about the wild success story that had come from his act of charity, and buy that breakfast I owed him.

At a restaurant in Jersey City — this time, kosher and bacon-free — we talked about his life and mine. I was working on applications to fellowships abroad. He was engaged to a doctor and they were moving out West for her job. We were both closing chapters in our lives and starting new ones.

Now I’m an English teacher in a Yeshiva similar to the one I attended, hoping to be the James that I wish I had when I was the students’ age. I’ve been to college and back, prepared to counsel the next generation of students who decide to venture to worlds unknown.