As he makes his arduous religious odyssey, it reminded me of some medieval quest where the gallant knight has to complete a series of tasks to win the hand of a fair lady.
“An ignoble knight and a very fair lady,” he laughs when we meet.
He was raised by “eccentric, bohemian” parents in what began as a mixed family. His Jewish father, a lecturer in English, enjoyed klezmer, Ladino ballads and tales of the wise men of Chelm. When Max opted to have a barmitzvah, his artistic mother decided to convert under the auspices of South Hampshire Reform Jewish Community. He and his two brothers were “dunked” in the mikveh too, although he declined the opportunity to undergo a sacral snip at that age.
That first mikveh ceremony felt like “a kind of ratification of who we all found ourselves to be and… the communities we have been part of, the festivals that we marked and connected us to the black and white photos on the wall of Bubba and Zeida and even further back, to our relatives from the old country”.
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The comedian and former pro-wrestler (Credit: John Hunter)[Missing Credit]
His Jewish identity had been “presented as something I could embrace and explore or to walk away from. It had always fascinated me… and I had always felt drawn, as facile as it might sound, to the warmth of the candles and the understanding there was something ceremonial and traditional we were tapping into.”
Nearly 20 years after his barmitzvah he was performing at the Edinburgh Festival in 2019 when he met the woman who was to transform his life, and test his identity: Eliana Ostro, whose play Anything With A Play was staged at the festival and whose debut novel is due to come out later this year.
They soon became a couple but there was one thing that threatened to block their vision of a future together. She was from a modern Orthodox family and kept Shabbat: in her religious world he was not Jewish according to halachah and that, for her, would prevent them marrying.
They were two people with “profound and very differing senses of their own identity and, particularly in Eliana’s case, the family ties and her grandfathers who survived the Holocaust,” he reflects. “It was this deeply felt connection that, as painful as it was to know this principle separated us, maybe made it impossible for us to be together. It was something I could understand and empathise with… It wasn’t just the family ties – it is deeply important to Eliana in a spiritual, religious core level.”
They broke up for a while but still talked about “what it might be like to be married”. Eventually after many “knotty, dense, theological conversations” between them, in late 2020 he applied to start an Orthodox conversion under the LBD. He entered it, he says, with “an open heart and total sincerity”. The LBD’s course is notoriously challenging. “I am nothing if not a wild optimist… I feel like if something instinctively feels right, then even though there might be logical signposts possibly flashing you in the other direction, I think there is something to be said for following your heart.”
He began attending synagogue daily and keeping Shabbat and – what was an “unbelievably difficult part of the process without a shadow of a doubt” – renounced any physical contact with Eliana.
“We were fortunate in lots of ways that we were able to find support at the most crucial moments”. His prospective in-laws, the Ostros, helped to find him a flat near their home in Primrose Hill. His parents were supportive, too. “If it had devastated and upset my parents or my brothers even, I don’t think it could have happened,” he says.
But there was a shock in store. When the time came that the Beth Din required him to move in with a frum family in a more religious part of town, they also wanted Eliana to take the “stairway to Hendon”. The book recalls that her face “froze”. After initially being “gobsmacked” by the demand, “we realised pretty soon after it was the best situation. It helped that she found an unbelievably welcoming, generous family and she was able to stay metres away from me. It kept us in one another’s orbit.” On one walk in the park, they held a glove of the other in their hand because they could not hold each other’s hand.
Those rare weekends when she was away, I really felt in over my head. It was wonderful...being near my partner even if she was down the road in a different family’s home
“Those rare weekends when she was away, I really felt in over my head. It was wonderful… being near my partner even if she was down the road in a different family’s home.”
The book paints colourful vignettes of Orthodoxy in action from a whisky-fuelled conga at one outdoor Kabbalat Shabbat service to a moon dance in a car park. (Not a homage to Van Morrison but the ceremony of kiddush levanah, a blessing on the full moon). In a poignant moment, he is given a silent blessing by the stroke-stricken Dayan Ehrentreu, who is no longer able to speak.
“The welcome we received was extraordinary at every possible level,” he says, recalling “the immense Shabbat feasts, which I am still digesting to this day. The openness and interconnectedness and sense of community was something I wouldn’t have experienced had we not spent that time there.”
But the book does not conceal his exasperation with the rigidity of London Beth Din. At one point he is summoned before the dayanim, who disapprove of his career. In a line that might have come from a Woody Allen film, he is asked, “Comedy… Is that really a job for a Jew?” And even after nearly three years when his Orthodox apprenticeship is almost over, the Beth Din has a fresh surprise: after marriage, they want Eliana and him to commit to remaining in Hendon for several years lest their Judaism become diluted in less holy suburbs.
On the very day that the dayanim are waiting for him at the mikveh to complete the conversion, Eliana’s father Maurice assures him that he need not go through with it.
“He said, ‘We don’t want this to be a thing that casts a shadow over your life together and if that is what this will do, you need to know that we will accept you.’ I think that was a profoundly meaningful conversation because it meant I had a moment of calm.
“It was a sort of reset. As tense and conflicted as the journey had been, it meant I could think clearly. I could walk away, and flip the table over and go in a different route from Eliana. But if I did, it would ensure I never would be able to participate in Jewish life in lots of ways that are unbelievably meaningful for Eliana.
“It meant that I could enter into that final moment with open eyes and an open heart and the knowledge this would build the foundation for the next stage of our lives.”
Afterwards he recalls “walking down the road on a gloriously sunny day with Eliana phoning her parents and listening them on speaker-phone just weeping with happiness”.
Throughout the conversion process anxiety had grown that his father, who had been diagnosed with dementia, and Eliana’s beloved grandmother, soubriqueted Lion, would be unable to make it to their wedding. But both were there to celebrate when it took place at a country retreat in Devon in late 2023.
The happy couple on their wedding day (Credit: Divine Day Photography)Divine Day Photography
“It was so joyful to make it to the chupah that weekend,” he says. “The overwhelming joy and happiness and celebration of that moment, that stays with me, and that I am sure I will retain for the rest of my life.”
Many times, Eliana and he had felt “on the ropes”, he says, and after the “deep bruising” left by the whole conversion ordeal “everything post-chupah has been a gradual…. healing process”.
After a year of married life, the couple resettled out of the heim in Swiss Cottage and attend South Hampstead Synagogue, though they still have “a lot of time for the wonderful people we met” in Hendon, he says.
I haven’t sought to repudiate anyone. I remain very close to all the wonderful people I grew up with
And while some converts turn their back on their past, he says, “I haven’t sought to repudiate anyone. I remain very close to all the wonderful people I grew up with and the wonderful community we are part of now.”
When revisiting some of the more difficult experiences during writing the book, he confides: “I would be anxious, pacing around my room.
“My blood pressure would be up, my heart would be thumping in my head and I might re-experience the same fears and anxieties that I did at the time.
“But day to day I don’t live with that. I live in a state of perpetual optimism leaning towards the next joyous event or happy occasion. And that’s my approach to life, I think.”
Making the Cut: An Unorthodox Love Story, by Max Olesker, Ebury Press, is out now
