Contrary to initial assumptions, it was surprising to learn from the eponymous blogger behind the Jew In The City that the website’s moniker is NOT based on the popular HBO series. Allison Josephs, who in addition to educating the world about Orthodox Jews also learns Torah together with Emmy nominated actress Mayim Bialik, revealed that the name comes from an even less likely source: an Internet web series based on the life of a teenage girl.

“When I read the New York Times article about lonelygirl15, I saw that through the medium of YouTube people can be made to feel like they know you,” explained Josephs. Through her blog and videos on Jew In The City, which she named after her Orthodox yet urbanite self, Josephs has made it her mission to improve Orthodox Judaism’s PR and break down stereotypes one by one.

Josephs traces her spiritual journey back to the tender young age of eight, when she claims she had “an existential crisis” because “no one knew, including my parents, what we were living for,” she explained. In fourth grade, Josephs’ questions deepened after her friend and classmate  was murdered. Later while in her teens, Josephs met a teacher  in her Hebrew High school who she credits with helping her discover the Torah lifestyle, giving her the purpose and meaning that she had been searching for. Her spiritual journey continued in Hawaii where she had a life changing experience in a tropical rain forest and realized that there must be a G-d in the world. She studied in Israel before and after college.

After working for several Jewish outreach organizations, including Partners In Torah and NCSY, Josephs decided to use those experiences to strike it out on her own.

“When I quit my jobs to start JITC there was no seed money or business plan, I just felt that I had a message to share with the world and it was time to share it” she explained. “And thank G-d,  although the first 4 and half years were a big struggle as I was essentially working for free… as of January I started focusing on public speaking and have been booking regular speaking engagements since then. Also, Freeda wigs has been putting ads on the videos in the last few months and YouTube made JITC a partner, so between all those things I’m finally making as much as my babysitter!” she says, laughing.

“A lot of stuff I talk about are  issues people have with 20th century western thinking” such as conflicts between science and the Torah. While Josephs herself is knowledgeable on a variety of Jewish topics, she consulted her rabbi who suggested she read, “The Science of Torah” by Natan Slifkin to research her ‘Torah’s view on evolution versus creationism’ video.

Josephs also proves to be an adept and entertaining actress in her videos, in which she sometimes plays characters wearing a variety of different wigs and talking in a range of accents and languages depending on her character, from a hurried “New Yawk” accent in the Shabbat video, to speaking French while wearing a beret in the Jewish afterlife video. Bialik also guest-stars in a couple of her videos, including one where she is identified as her 1990’s TV alter ego “Blossom.”

Yet despite being deeply religious, Josephs never preaches or comes across as judgmental and projects her ability to relate to secular Jewish audiences due to her own upbringing. “I can understand where they’re coming from because I myself use to wear bikinis and eat bacon cheeseburgers – I still miss them sometimes,” she admits. “I went to prep school and I spent my life around people different than me and see that there are different people out there, and then I get upset when I see negative attitudes towards others from Orthodox Jews, when we are all from Adam, we are all created b’tzelem Elokim, in the image of G-d.”

At the same time, Josephs doesn’t expect to elicit a positive reaction from everybody. “I’m not so naive to think that I’m going to change Nazis with cupcakes,” she deadpanned. “One time I got a complaint from a guy saying that I wasn’t accurately depicting “the Orthodox reality,” so I told him, “I may not be accurately depicting your Orthodox reality, but I am accurately depicting my Orthodox reality.” I try to be honest about the things that are challenging in Orthodox Judaism,” she said.

While some Orthodox groups may bridle even at the thought of surfing the Web, Josephs embraces technology as a positive way to inspire and educate. “Is being in online videos tznius (Hebrew term for modesty)? Well I dress tznius and act tznius, so yes, I believe it is, but it’s certainly not as tznius as not being online at all,” she explained. She continued: “The way I see it, there is often a tension when it comes to Jewish law – with JITC I’m at a higher level of the reaching out to my fellow Jew mitzvah but it means the tznius has to suffer somewhat. I can’t throw tznius away all together because it would be better for outreach purposes. I need to be within the parameters of Jewish law no matter what, but excelling at one mitzvah might mean another mitzvah might not be at the highest level. That’s a principle I learned years ago and it applies to many areas of life.”

Upon discovering recently that Bialik was injured in a car accident, Josephs described that it “was so surreal to find out she had gotten hurt on Facebook…we had spoken the night before and were supposed to learn just a few hours later. I emailed and called several people she’s close with looking for more information.  thank G-d she is ok and although she’s in a lot of pain, she is also very full of faith.”

The pair were set up in a way that Josephs cheekily claims that “Hashem (G-d) was the shadchan (matchmaker).” While Josephs was studying in Israel in 2002 she came up with a random thought – what happened to Blossom?  “And I found out she was in college majoring in Judaic Studies, and I thought to contact her through Partners in Torah. I attempted to reach her but quickly realized her contact info would not be listed anywhere, so I gave up, but then four years later she joined Partners in Torah on  her own and we got matched and we’ve been learning together for six years. Last year we did a fundraiser together where the reporter wrote down a funny thing I said: I cant say I knew her before she was famous but I can say I knew her before she was famous again!”

Together, Bialik and Josephs are about to begin studying Aggadic works such as the Ein Yaakov and have studied Jewish philosophic works such as Rabbi Joseph B. Soloveichik’s Halachic Man, the rabbinic laws of Shabbat observance, including the 39 melachos. Josephs’ personal favorites also include the mystical philosophy of Rabbi Aryeh Kaplan.

Despite having a bachelor’s degree in philosophy from Columbia University, Josephs feels that while her Ivy-League education gave her certain advantages, it doesn’t offer everything. “While I did well  in school, I never really thought of myself as studious,” she confesses. “I wasn’t a bookworm in the library, I would be organizing Jewish events on campus instead. You see college dropouts do amazing things and then there are plenty of people who are smart and self-taught. The best thing that Columbia did for me was that it opened up doors, but when I left Columbia to learn in Israel, I found the Jewish philosophy courses to be more impressive than the classes I took at Columbia.”

Describing herself as a right wing modern Orthodox Jew, Josephs subscribes to philosophy incorporating Torah U’Madda, which is translated as “science” or “worldly knowledge,” but with the Torah as the guiding lens. “The Torah has to be the guiding line. I believe the Torah is truth and you can experience those truths  in the larger world. I speak as someone who up until now lived at least half of my life as secular. I had learned many wonderful things. Right now I am working on a food memoir which traces my spiritual journey and uses the treif (non-kosher) foods I grew up with, which I converted into kosher versions when I became observant as a motif. The message is that to be a spiritual person, you need not lose your flavor.”

A spiritual message indeed, that Josephs would like to impart on her children, starting by teaching them how to have a deep connection  to G-d. “For me, everything started with Hashem, and the most important gift a parent can give is instilling in his/her child a connection with G-d,” she said. Ever the multi-tasker, Josephs concluded the interview with “now I have to go eat my dinner.” It was ten O’clock at night.