My fiancee, my foreskin and me: the comic who turned adult circumcision into a jaw-dropping show

To be with the woman he loved, Max Olesker had to convert to Orthodox Judaism – which required an unwelcome operation. He relives a painful and sometimes infuriating journey

When Max met Eliana at the Edinburgh fringe, the romcom vibes were strong. Shots, songs, falling headlong in love. Less vibey was the conversion Max Olesker had to navigate to marry his Orthodox Jewish beloved. The comedian had always thought of himself as Jewish – when his parents married, his mum converted to a less rigorous branch of Judaism. But to the Beth Din, the rabbinical court, that didn’t count. To be with the woman he loved, Max would have to go all in – including undergoing an unwelcome adult circumcision.

We’re chatting at a kosher restaurant in central London. Olesker, 38, pulls out a camera, snapping his hefty salt beef on rye from several angles (“I’m trying to learn a skill”). As on stage, he’s an engaging presence: bright eyes, smart, ribbed knitwear, unwaveringly polite. He would surely be a credit to any religion.

Yet, as the book and show that chart the agonising process attest, it’s not that simple. His tale sent me into scalding fury at the Beth Din, this all-male panel wielding inscrutable power over their supplicants. They delay, they demand, they withhold approval and bark: “Is comedy a job for a Jew?” (How did they respond to Olesker’s comedy wrestling? Don’t ask.) The sluggish pace feels especially cruel as Max’s dad endures dementia and Eliana’s grandmother advances into her 90s.

How did Olesker remain sane through what feels so capricious a process? “There’s little evidence that I successfully kept myself sane,” he smiles. “It was extraordinarily challenging.” He’s not gunning for the rabbis, he insists, but “I wanted to communicate the way it caused me a great deal of pain and anguish, and put extraordinary stress on my relationship. It pushed us incredibly close to the line.”

Keeping a journal helped corral the sheer oddity of the journey – especially when lodging with an Orthodox family, feeling like their thirtysomething foster child. “It was so dislocating,” he says, “sat at the edge of a single bed, using an ironing board as a desk. I began writing so that I wasn’t just staring at the ceiling with anxiety dancing through my brain.”

During those sleepless nights, did Olesker think: this material is golden? “Definitely not,” he says. His daffy shows with comedy partner Ivan Gonzalez (as Max & Ivan) increasingly tapped an autobiographical impulse, mayhem amplified by emotion. But with the conversion, “it was only when things began to go disastrously rough that it began to feel that some sort of emotional reflection was the way to process it. None of us could have predicted the juddering crawl towards the finish line – I felt it was sitting on the top of my psyche and had to be engaged with.”

His captivating memoir is now distilled into a 60-minute show. The title, Making the Cut, refers to circumcision – but we’re eating, so we don’t go there as Olesker tucks into his meaty tower. More broadly, his path is “a zigzag thing – a journey that was funny, stressful, frustrating and heartbreaking at various points, and none of it in a straight line”.

Scribbling is one thing – performing your rawest moments to a roomful of strangers must be another? “It was both draining and energising,” Olesker confirms. “Catharsis is perhaps the word. At times I choked up and struggled to get through the show.”

It must also hit differently to perform this show at what is, as Olesker acknowledges, “an incredibly strange time to be Jewish. Jews of all stripes have found themselves contemplating their identities and their relationship to Judaism. I’m aware of so many fraught conversations. For me, part of the importance of the show was creating a story that [followed] the complexities of the human Jewish experience, through all manner of Jewish communities, and to write something reflective of that lived experience.”

Wrestling Max and comedy Max are now making space for theatre Max. In Edinburgh, Making the Cut was listed as theatre rather than comedy. “It was a leap into the unknown,” Olesker says, though full houses followed. Olesker embedded himself in the city’s small Jewish community, and was caught up in “intimate personal conversations with audience members who I think found it moving seeing a Jewish story reflected on stage. I would find myself connecting to audience members in an intense way I hadn’t experienced previously.”

His next project with Ivan is an actual play. The Wedding(s), premiering at London’s Park theatre in late spring, follows two hapless brothers as they manage clashing celebrations at their ramshackle wedding venue. “They’ve got to keep them apart in order for love to reign supreme. It’s a farce with a heart.”

The sandwich has been elegantly dispatched, but before we leave, I wonder: has Olesker’s conversion had an impact on his work? “This is the first show in which I’ve identified as a Jewish person from the get-go. Although I consider it first and foremost a love story that has Judaism in it, it’s also a Jewish story through and through.”