Question: "What's your religious background?"
Answer:
I grew up in Indiana, in a very non-Jewish area. Actually, there was a sizable Jewish community in Indianapolis – and most of the Jewish kids went to the private Jewish school. As a result, my parents were afraid that there would be virtually no Jews in the public schools and non-Jewish kids would grow up having never met a Jew before. My parents jokingly called us “Ambassadors for the Jewish People” (no pressure!

) and sent us to the public schools.
My dad’s dad (who recently turned 101!) is a classic reform rabbi, and my mom, who was raised Conservative, had a lot of Chassidic extended family. So they “met in the middle” (so to speak) and raised us Conservative, but at a Reconstructionist synagogue.
Judaism was a big part of my identity and life as a kid. My family observed Shabbat and kept kosher – not completely, but both were very strong values for me. II faced a lot of anti-semitism at school, but also, just the fact of my being there really helped people to understand and relate to Jews as human beings. I think about that a lot today, when I write so much and so publicly on social media about being a trans woman. Visibility matters. I learned that as a kid.
I became gradually more observant in high school and college, drawing on the deep love of Shabbos and kashrus that my parents had instilled in me, which was really more the process of becoming myself as I gained more independence from my parents. Actually, in hindsight, I think it was partly my way of further deluding myself into thinking I was really a cisgender man. I wanted to be “the nice Jewish boy” I thought everyone expected (spoiler: it’s not what people expected!) so I grew a massive beard, went to yeshiva in Israel, started wearing tsitsit, etc.
Then I had a mini crisis. I spent a few months at a male-only yeshiva in Jerusalem and, honestly, I loved the learning, but I hated being in a male-only space. I had no idea why, but egalitarianism was very important to me (and still is), so then I went to the Conservative Yeshiva (co-ed) where I met a girl and got engaged after 10 weeks. But even there, I was unhappy. I felt like I didn’t belong in any one movement; I admired them all, and I hated them all. So I started to just call myself a Jew. ¯\_(ツ)_/¯
Got married in 2011, my wife became a conservative rabbi, and I became a “rebbitser” — “the rabbi’s husband.” (Now we're divorced, pending some final paperwork, after 10 years of marriage.)
So much to say about being the rabbi’s spouse and all the gender issues along with it!
Over the past 5 years or so, I grew increasingly disillusioned with the world, which I now realize coincided with the onset of serious gender dysphoria and bathroom anxiety. I became disillusioned with academia. I became disillusioned with the medical field. I became disillusioned with Zionism. I became disillusioned with the very concept of objective truth, with the rigid structure of binaries, and with the infallible authority of academic scholarship. I stopped praying daily, stopped wearing a kippah, and questioned the existence of G-d and my sense of belonging in the Jewish people.
And then my egg cracked, and by the summer of 2019 I’d realized I’m a trans woman and my whole world simultaneously shattered and made SO MUCH SENSE. Incidentally, I’m apparently the first person ever to come out as a trans woman while married to a synagogue’s rabbi, so the Jewish Telegraphic Agency ran a story about me and it was translated into 5 languages and basically I had no privacy.
Now I call myself Orthodox, which seems right now the best-fitting label for me, and I actually find the binary gender structure very validating – I’m treated intentionally as a woman! So I’m actually, oddly, finding a lot of spiritual meaning and satisfaction in sitting on the women's side of the mekhitsa, etc.. But gender egalitarianism is still very important to me, as a matter of principle. I hope that someday I’ll feel comfortable wearing tallit/teffillin/kippah, reading Torah, etc again, but right now it just causes me so much anxiety about being misgendered and reminds me of my days as a “nice Jewish boy.” Life’s complicated, you know? But I’m shomer shabbos and keep strictly kosher, and Jewish spirituality, practice, and values flow through my blood.
So that's my answer, "al regel achas" (on one foot), to the question of my Jewish background. Obviously, there's a lot more to say. But, you know... I could write a book about it. :-)