In much of the Jewish online world, a blog post about someone enjoying Shabbat services would either be mundane, or, at best, a delight for some parental types. But on Heshy Fried’s blog, such a post attracted 224 comments and counting. Some of them chastise the blogger (“Your people contribute to Judaism’s death by assimilation that has spiritually destroyed as many, maybe even more Jews than the holocaust”); some laud him (“I think we all need a chance to step out of our own boundaries and share ideas”). Why the hullabaloo? The service in question was Reform, and Fried’s blog, Frum Satire, has a largely Orthodox readership.

As someone who straddles the line between the Orthodox and secular worlds, Fried catches flak from all sides. The website Jewschool.com refuses to publish him; an editor there found his work offensive to women rabbis. (In truth, Fried supports the ordination of Orthodox women, one of the few bloggers from the Orthodox world willing to engage with the topic openly.) He’s also had trouble with The Jewish Press after a piece of his gently mocking the custom of Kiddush (a light meal and wine following the morning Shabbat service) generated some negative responses from readers, including one whose daughter found the word “horny” on Frum Satire.* “Dude, you publish Shmuley Boteach every week!” he responds. “Give me a break.”

The Orthodox blogosphere is full of irreverent and dissenting voices, from the slightly miffed career girl at Frum N’ Flipping to the frankly repellent (and aptly named) Religious Pervert. But most are anonymous, and Fried said “have an axe to grind.” Fried is something of a searcher, and he takes a light hand in exposing what he describes as the “caste system” within Orthodoxy, providing “an insider sociological view.” His posts fall into two main categories: either poking fun at the religious world for things like “kosher GPS,” or those taking issue with some aspect of Orthodoxy, such as homophobia.

Fried, 27, was born and raised on the Upper West Side of Manhattan, where his parents kept a Modern Orthodox home. His mother died when he was six years old, leaving him and a younger brother, who now lives in Colorado, in the sole care of their father. Fried attended a Modern Orthodox day school for his elementary years and then, in high school, went to what he calls a “black hat” boarding school, living in a dorm with ultra-Orthodox students from around the country. For college, he went to SUNY-Brockport, a public college in upstate New York, where, he said, “I had a lot of redneck friends.” These experiences helped him “sort of chameleonize,” he said. Nowadays he’s not sure he even considers himself Orthodox—“I like the term ‘Jewish’ better”—though with his with his unkempt hair, constant need for a shave, scruffy clothes, and long limbs dirty from hours of nighttime bike riding, others might classify him as a Modern Orthodox hippie. Praying, he has said, is like “going to the bathroom; it’s just something I do.”

His father, who is 71, recently remarried a woman 24 years his junior and moved to Far Rockaway, a distant part of Queens; Heshy Fried calls it “a terrible place.” He describes his father as a die-hard Republican with an extremely conservative attitude. But, in fact, when I tagged along on a visit, I found Ziggy Fried to be a cranky but open-minded man who likes the Lower East Side of Manhattan because, he said, of “the weirdos, the hookers, the lesbians, the people from Kentucky.” “It’s important not to be a conformist in thought,” he added.

It’s a lesson the younger Fried has obviously taken to heart. To make money, he works for a company that buys and resells used cars, but his avocation seems to be as a kind of Pied Piper for people who, like himself, don’t quite fit in. He lures fellow travelers with jokes and acute observations about life. And he enjoys his solitude: Fried tries to spend three days of the week camping and hiking in the woods of New York State. (He keeps a sort of phantom blog—Frum Outdoorsman—filled with his musings on Americana, the Road, and Nature.) In 2007, he briefly worked as a private investigator in Albany, trying to catch people cheating on workers’ compensation insurance. He got the job partially because he owns a bike, a car, and a kayak (the last of which he used to “sleuth around” a suspect’s beach house), and was willing to sit in the woods all day reading a book. “I’m a certifiable treehugger,” he said. But he soon quit. “I was all by myself,” he explained. “I need interaction. I’m an extroverted loner. I might go into the woods for a week by myself, but I need to come back and talk to people.”

Fried started writing in 2006 while interning with the New York State legislature during budget season; some nights, he had to hang around until 2 a.m., and posted his thoughts on Craigslist’s “rants and raves” section. A friend suggested he create his own site. Now, he said, he gets approximately 50,000 visitors a month. This year, he is attending the ROI Global Summit in Israel, a conference for “young Jewish innovators,” and he’s simultaneously trying to get into stand-up comedy.

It’s Fried’s talent for gently satirical taxonomies that further sets his blog apart. He has broken down types of Orthodoxy by yarmulke style, and has written a “Guide to Jewish Newspaper Advertisements.” And it appears that the ladies online love him for his irreverence. They leave innuendo-filled comments, or profess outright their desire for him. Fried said he has received sexual solicitations via Facebook, including one from a 29-year-old married woman who asked him to have an affair. (“I was like, ‘You’re hyphenated, I’m not going there.’”)

“People are very quick to pull the ‘chillul hashem’ [desecration of God’s name] card,” he said. “I went into a restaurant and I was joking around with the guy—I said, ‘Hey, wanna give me a free dinner? I’ll write a review about you on my blog.’ He said ‘What’s your blog?” and I said Frum Satire, and then he got really pissed and said ‘Man, I shouldn’t even serve you, I hate you. You’re the guy who did the video on shuckling.’” He takes most of this in stride; “If people aren’t telling me to go fuck myself at least twice or three times a day,” said Fried, “I’m not doing a good job.”

He considers himself “the person that will talk to you while you’re standing in line,” though so far his efforts to translate his talents into stand-up comedy have been received lukewarmly. (He had his first gig last November). Though full of quips (“I take off my yarmulke when I’m buying porn, or picking up change. In one case it’s for Jews, in the other it’s for non-Jews”), Fried is overzealous in soliciting feedback from awkward audiences of Orthodox singles, or, in one case, at an exclusive Orthodox men’s club in Brooklyn. The club hired him for a birthday party, where he was astounded to find a four-level bar, flat screen TVs, and a group of rowdy men with sidelocks. They didn’t like his show. “It wasn’t dirty enough,” he said. “They didn’t want Jewish humor, they wanted dirty sex humor. And racist humor. I don’t do that.”

A few weeks ago, we drove in his Subaru wagon from a stand-up gig at an Orthodox synagogue uptown to Chulent, a makeshift gathering for an ever-evolving group of outcasts from Orthodox society held in the upstairs of an old synagogue in the garment district. On the way, Fried talked about fellow irreverent writers: Benyamin Cohen, whose stunt book My Jesus Year, said Fried, was written “for hipsters,” and Shalom Auslander, who uses “language that’s easier for Orthodox Jews to understand.”

In other words, Fried is aware of the limitations of addressing an audience raised speaking Yiddish and schooled primarily in biblical texts, and often less familiar with popular literary conceits, ironic wit, or even difficult vocabulary words. (Fried himself was unfamiliar with the word “expat” when someone used it at Chulent.) It’s partly for this reason that he wants to branch out into the more “secular” Jewish world—Reform and Conservative congregations, cultural institutions, and publications—so he can make fun of them, too.

Chulent was suffocating—the rooms were virtually airless and smoke-filled, discarded detritus was scattered about, huge strips of paint were peeling from the walls. But in other ways it felt like true bohemia, with no trace of the faux-distress and alienation fashionable among people in the “secular world.” Fried might as well have been the patron saint of this community. He strolled about the party in the laid back but alert manner of politicians or journalists. Everyone knew him, and he seemed to know something about everyone.

At one point, Yitz Jordan, who raps as Y-Love, came into the smoky back room. People stopped talking and focused on him. Not Fried; he turned away, a bit bored, perking up later when someone brought him an Orangina. When we left, a scrawny Hasid by the door asked, “See you next week, Hesh?”

“Probably not,” was his reply.

*CORRECTION: An earlier version of this article stated that The Jewish Press had “blacklisted” Fried after receiving “50 letters calling him a heretic,” and that it was an editor’s daughter who encountered the offending word on his blog. Fried was mistaken as to the number of emails and the identity of the girl, and both Fried and a representative of the Press confirm that he was not prohibited from writing for the publication.