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‘Especially in this country, I feel you craved me. You weren't aware it but you required me, to alleviate some of your own shame.” The comedian, the forty-two-year-old Canadian humorist who has lived in the UK for nearly 20 years, was accompanied by her newly minted fourth child. She removes her breast pumps so they won't create an irritating sound. The initial impression you see is the awesome capability of this woman, who can radiate maternal love while crafting coherent ideas in whole sentences, and without getting distracted.

The following element you notice is what she’s famous for – a natural, unaffected ballsiness, a dismissal of affectation and duplicity. When she sprang on to the UK comedy scene in 2008, her challenge was that she was strikingly attractive and refused to act not to know it. “Aiming for stylish or pretty was seen as man-pleasing,” she recalls of the start of the decade, “which was the opposite of what a comedian would do. It was a norm to be self-deprecating. If you appeared in a elegant attire with your underwear and heels, like, ‘I think I’m fabulous,’ that would be seen as really off-putting, but I did it because that’s what I wanted.”

Then there was her routines, which she describes casually: “Women, especially, required someone to arrive and be like: ‘Hey, that’s OK. You can be a advocate for equality and have a enhancement and have been a bit of a slag for a while. You can be imperfect as a parent, as a significant other and as a picker of men. You can be someone who is wary of men, but is confident enough to criticize them; you don’t have to be pleasant to them the entire time.’”

‘If you took to the stage in your underwear and heels, that would be seen as really alienating’

The drumbeat to that is an insistence on what’s true: if you have your child with you, you most likely have your breast pumps; if you have the jawline of a young person, you’ve most likely received treatments; if you want to lose weight, well, there are medications for that. “I’m not on any yet, but I’ll look into them when I’ve stopped feeding,” she says. It addresses the root of how women's liberation is viewed, which I believe has stayed the same in the past 50 years: freedom means appearing beautiful but without ever thinking about it; being universally desired, but never chasing the male gaze; having an impermeable sense of self which God forbid you would ever alter cosmetically; and in addition to all that, women, especially, are meant to never think about money but nevertheless succeed under the relentlessness of modern economic conditions. All of which is sustained by the majority of us being dishonest, most of the time.

“For a long time people reacted: ‘What? She just speaks about things?’ But I’m not trying to be challenging all the time. My experiences, choices and missteps, they reside in this space between satisfaction and shame. It occurred, I share it, and maybe relief comes out of the jokes. I love telling people confessions; I want people to share with me their confessions. I want to know mistakes people have made. I don’t know why I’m so keen for it, but I feel it like a connection.”

Ryan was raised in Sarnia, Ontario, a place that was not notably wealthy or urban and had a active amateur dramatics arts scene. Her dad managed an engineering company, her mother was in IT, and they expected a lot of her because she was vivacious, a high achiever. She wanted to escape from the age of about seven. “It was the sort of community where people are very happy to live nearby to their parents and stay there for a long time and have their friends' children. When I go back now, all these kids look really recognizable to me, because I grew up with both their parents.” But isn't it true she partnered with her own first love? She returned to Sarnia, met again her former partner, who she saw as a teenager, and now – six years later – they have three children together, plus Violet, now 16, who Ryan had raised until then as a solo mom. “Right,” says Ryan. “Sometimes I think there’s an alternate reality where I didn't make that, and it’s still just Violet and me, sophisticated, urban, portable. But we can’t fully escape where we came from, it turns out.”

‘We cannot completely leave behind where we started’

She did escape for a bit, aged 18, and moved to Toronto, which she adored. These were the time at the restaurant, which has been an additional point of controversy, not just that she worked – and enjoyed working – in a venue (except this is a misconception: “You would be let go for being nude; you’re not allowed to remove your top”), but also for a bit in one of her sets where she mentioned giving a manager a sexual favor in return for being allowed to go home early. It crossed so many boundaries – what even was that? Manipulation? Prostitution? Predatory behavior? Lack of solidarity (towards whoever it was who had to stay late so she could leave early)? Whatever it was, you absolutely weren’t supposed to joke about it.

Ryan was surprised that her anecdote provoked controversy – she got on with the guy! She also wanted to go home early. But it exposed something larger: a calculated inflexibility around sex, a sense that the price of the #MeToo movement was demonstrative modesty. “I’ve always found this notable, in discussions about sex, agreement and exploitation, the people who don’t understand the complexity of it. Therefore if this is abuse, why isn’t that abuse?” She brings up the comparison of certain remarks to lyrics in popular music. “Certain people said: ‘Well, how’s that dissimilar?’ I thought: ‘How is it similar?’”

She would never have moved to London in 2008 had it not been for her then boyfriend. “Everyone said: ‘Don’t go to London, they have pests there.’ And I found it difficult, because I was suddenly broke.”

‘I was aware I had material’

She got a job in sales, was diagnosed an autoimmune condition, which can sometimes make it hard to get pregnant, and at 23, chose to try to have a baby. “When you’re first told you have something – I was quite unwell at the time – you go to the darkest possibility. My rationale with my boyfriend was, we’ve had so many ups and downs, if we haven't separated by now, we never will. Now I see how long life is, and how many things can alter. But at 23, I didn't realize.” She managed to get pregnant and had Violet.

The next bit sounds as white-knuckle as a tense comedy film. While on maternity leave, she would take care of Violet in the day and try to break into comedy in the evening, carrying her daughter with her. She felt from her sales job that she had no problem being convincing, and she had faith in her sharp humor from her time at Hooters; more than that, she says bluntly, “I was confident I had comedy.” The whole circuit was shot through with sexism – she won a major comedy award in 2008, just over a year after she’d started performing, a prize that was conceived in the context of a persistent debate about whether women could be funny