Darren O'Donnell is trying to make you uncomfortable, and he will do almost anything to help you enjoy the experience. He will take you to an unfamiliar neighbourhood to knock on the doors of strangers and ask for tours of their homes, or get you to talk about your entire sexual history on camera and again in public, or give you over to the administration of children who will teach you something new or cut your hair. He will find any way he can to get you to encounter people you don't normally deal with, in ways that feel strange and that may crack open the orderly social compartments we live in. What he will not do, as artistic and research director of the Toronto performance company Mammalian Diving Reflex, is serve up a prepackaged experience that you can consume while you hide in a darkened theatre.

For the past decade, the sometime actor and playwright – and current masters student in urban planning – has pushed beyond the proscenium arch into a type of civic theatre "that sees the city as a stage, and all of the people in it as actors," as he told novelist Sheila Heti in 2011 when she interviewed him for The Believer. O'Donnell's community-based works have been enacted around the world – Haircuts by Children, a pivotal 2006 piece that gave kids a quick course in haircutting and a public venue to show off their skills, has been recreated in 28 cities in nine countries.

MDR has become so successful abroad, and so dependent on revenue from foreign festival appearances, that in the past few years O'Donnell has had to recultivate his company's roots in his own community. "We lost touch with Toronto," he says. Part of his solution was to take on as equal colleagues a team of Parkdale teens he calls the Torontonians, mentored by a slightly older professional group called the Young Mammals.

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Earlier this week, O'Donnell put himself in a somewhat uncomfortable spot, playing a doped-up-looking Toronto Mayor Rob Ford in a re-enactment of the video whose rumoured existence has transfixed the city. It wasn't O'Donnell's idea – he was going along with a proposal from one of the Torontonians, whose ideas for what MDR should do are, in his view, as valid as his own.

"I try to foster a climate in which people can really just do what they want," he says. "I have as much of a veto as anyone, but certainly no more."

As much as anyone, but certainly no more. That simple valuation describes not only the way things are decided at MDR, but an ideal of freedom and equity in a civil society. MDR's works can look like interactive street art, or theatrical ice-breaking, or social work, but they're all about coaxing people to act out an ideal of social relationships. The question is always how far people really want to go in that direction.

"He takes on these serious issues about how people relate to each other, across class or age or whatever," says Misha Glouberman, a Toronto social facilitator who participated in a future-oriented MDR piece from 2006 called Diplomatic Immunities. "And he does it in a way that balances seriousness with humour, and utopianism with a fair amount of skepticism."

O'Donnell's practical idealism had a difficult birth, through two decades of performing other people's plays, writing his own, and gradually losing faith in the point of it all. "The European tradition of representational theatre as an active part of a civic discourse is more or less finished," he writes in a 2006 memoir and manifesto, Social Acupuncture, the first part of which surveys his years as an "idiot" writing "shitty little plays."

He came into contact with the ideas of others who had puzzled over the social relevance of the conventional arts, including art theorists Nicolas Bourriaud and Claire Bishop, theatre director Jerzy Grotowski, and political analyst Guy Debord. Throughout the 1990s, people in Toronto and around the world were finding new ways to get out of galleries and theatres and engage people directly, in more or less structured encounters that became known as "live art" or "relational art."

In 2003, spurred by Toronto's SARS outbreak and the fear of social contact it provoked, O'Donnell organized a series of events call The Talking Creature, in which people fanned out through a neighbourhood and recruited strangers to participate in unstructured conversations. He was struck by how most people approached were "totally game," by how uncomfortable the encounters initially were, and by the fruitful nature of that discomfort.

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"You can't become more socially adept without the experience of feeling awkward and being okay with it," he says. "It's like when you're tackling a new math problem – you have to go through a period of confusion in order to understand the problem."

Tenzin Chozin, a 17-year-old who has been in the Torontonians since it began in 2009, says his awkward moments come when he has to stand on a stage and present work, "because I'm not very outgoing." His biggest MDR experience came with Dare Night (2011), in which teens try to complete the most courageous dares – a straightforward-sounding assignment, but one that required months of event-planning workshops, as Chozin and others learned how to market and promote the project: "We did everything from scratch." His Tibetan-Canadian parents haven't seen any of his work with MDR, but they're happy about it, he says, "because it keeps me out of trouble. And I guess I feel more confident about the future."

In All the Sex I've Ever Had (2010), elderly people led the charge into the awkward zone, opening up about their erotic experiences in front of an audience that asked questions and expressed opinions. The piece, which just finished its fifth iteration in Glasgow, "isn't about taking a prurient trip through someone's sexuality," O'Donnell says, "but about the openness that's generated in the room." With each group of seniors, he does hours of taped interviews, and edits the results into a script that they read. "We structure it formally, though they provide all the content," he says. The same goes for much of his work with the Torontonians, whose latest project is an ongoing series of encounters with other arts youth groups in Toronto .

Eventually, O'Donnell says, the Torontonians will take over MDR. He sees this succession as another expression of what his kind of social art and "stealth pedagogy" involves. It's not about sparking a revolution, as Guy Debord and others may have had in mind in the late 1960s. It's about changing individual lives, reconfiguring local relationships, and returning human connections to the centre of our social reality.

MDR will present Future Tastes of Toronto: At the Kids' Table at Toronto's Luminato Festival, June 15 and 16.

MDR will present Future Tastes of Toronto: At the Kids' Table at Toronto's Luminato Festival, June 15 & 16.