Mordechai, a 31-year-old Orthodox lawyer from Toronto, gave his wife a Jewish divorce this summer.
Then he began his life as Nicole, a woman.
Nicole isn't the first transgender person to live an Orthodox life, but as far as anyone knows she is the first Orthodox person to transition publicly and "in place." Transsexuals may always face obstacles and taboos in mainstream Western societies, but Orthodox Jews who make the transition face even greater complications.
"I'm not challenging halachic Judaism and I don't want it to be perceived that way," Nicole said, referring to Jewish law. "It would be easier for me in some ways to reject Judaism and the Orthodox community, but it's what I believe and value, and [transitioning] isn't a rejection of any of those things but an affirmation of them."
"Ninety-nine percent of Orthodox Jews who transition do not stay frum," or religiously observant, said Beth Orens, the pseudonym of one Orthodox transwoman from the Midwest who is the most visible and prolific Internet presence on issues of Judaism and transsexuality. "It takes a certain amount of stubbornness to do so.
"I've corresponded with a couple of yeshiva guys who were thinking about it," she continued. "About two years ago a guy on the Dina list" - an e-mail list Orens established to create a meeting place for Orthodox transsexuals - "killed himself. He couldn't deal with the repercussions of transitioning."
Orens and Nicole also recently started dinablog.wordpress.com, a Web log for "Orthodox-by-background transpeople and their families."
The Dina list, which includes Jews from the United States, Israel, Canada and the United Kingdom, has fewer than a dozen members. It's difficult to determine what percentage of the population, Jewish or otherwise, transsexuals represent: The US Census Bureau does not count transsexuals, and many people who make the transition do not wish to be counted.
The data most often cited by the American Psychiatric Association, based on a decadeold European study, suggest that roughly one in 30,000 adult males and one in 100,000 adult females seek sex-reassignment surgery.
Most gender advocates put the numbers much higher, with one study claiming that based on calculations of the surgery performed in the United States, at least one in 2,500 adult males in the US has become a woman.
Orens, who is 43, was 32 when she transitioned and 33 when she had the surgery.
She was married for eight years before her transition, and her ex-wife has barred Orens from seeing their two children. Though she moved to New York from Israel to transition, she moved back to Israel after her surgery.
Five years ago, however, after being "outed" on a bus by a former close friend, she returned to the United States with her new partner and their 6-year-old daughter.
Orens and her partner live in a suburb 10 minutes from where she grew up. At the modern Orthodox synagogue they attend, she sees the parents of an elementary school friend, someone she knew from high school and even her college roommate.
"It's like I'm a ghost," she said. "Nobody knows who I am."
Dr. Dana Beyer, a retired surgeon in Chevy Chase, Maryland, said "Nicole is the first Orthodox woman that I know of to transition in place publicly."
Beyer, 54, a transwoman who, like Nicole, attended an Orthodox yeshiva for boys as a child, is now Conservative and recently ran for public office. She is an activist and advocate on civil rights and medical issues.
"From when I was seven years old, I knew I was a girl," Beyer said. "Standing there with the boys, saying 'she'lo asani isha' every morning," the prayer where men thank God for not making them female, "it was like swallowing crushed glass."
It took Beyer another four decades to become a woman. Along the way she had two children with her first wife. When she began to transition in 2000, she and her second wife divorced.
In 2003 Beyer had surgery on her face and genitals. Now she describes herself as a single Jewish woman and attends a progressive, egalitarian Conservative synagogue.
"Only Reform and Reconstructionism say that [transsexuals] are specifically welcome, and I'm not Reform," Beyer said. "But I went to my Conservative rabbi and made a case and he said 'okay.'"
In 2003, the Reform movement's Hebrew Union College admitted Reuben Zellman, who became the first openly transgender person accepted into a Jewish rabbinical school.
In December 2003, the Conservative movement officially recognized that those who have undergone full sex-reassignment surgery "are to be considered as having changed their sex status, and so recognized by Jewish law."
Their decision relies on the responsum of the Orthodox halachic authority Rabbi Eliezer Waldenberg, known as the "Tzitz Eliezer," in which he states that sex status is determined by the external genitalia, even if surgically constructed.
The Orthodox community does not accept this as the majority opinion, however, and it is unlikely that Nicole will have as easy a time in an Orthodox synagogue.
A rebbe with whom she is still close told Nicole that although transitioning is not permitted halachically, there probably is still more room for it in Jewish law than in Jewish society.
Rabbi J. David Bleich, an authority on Jewish law, ethics and bioethics who has written about transsexuals from an Orthodox perspective, agreed.
Transitioning "is an impossible situation," Bleich said. "Shul is the least of such a person's problems. If such a person is looking for acceptance, it's not in the cards. He should be happy if people don't criticize him to his face."
"Maybe transitioning was wrong, was 'asur,' " or forbidden by Jewish law, said Orens, who like many Orthodox women does not shake hands with men and wears sleeves cut below her elbows. "We believe that this life is not all there is, there is 'olam haba,' " or afterlife. "Maybe I shouldn't have transitioned, lived as a boy and died miserable.
"But it's natural for people to want to save themselves," she said. "If I made a mistake, I'll find out when I stand before the 'kiseh hakavod,' " or God's throne, to be judged, she said.
"Or maybe [God] will say, 'I'm so proud.' I did what I had to do and so did Nicole," she continued. "It's not a question of whether it's acceptable, but that we had to do it."