The morning after the ceremony, Waller-Bridge showed up at Scott’s hotel room for a hungover debrief. The after-party drink, for the record, had been a vodka gimlet. “The gimlet came into my life about a year and a half ago,” Waller-Bridge said. “I have really always wanted a cocktail that you order with total confidence; you know, that thing that you order and everyone’s like, Holy shit, she knows what she’s doing with her entire life.” Even if the picture was glorious, it wasn’t exactly role-model material. I asked Waller-Bridge if she gave the friend who took it permission to post it on Instagram. “He always asks for approval,” she said. “And I was like, Yes, fuck yes! Approved. So approved.”

WALLER-BRIDGE’S sense of mischief comes from a place of security. She grew up in Ealing, a genteel suburb of London, with baronets and a member of Parliament in the family tree. (“Is Phoebe Waller-Bridge a Tory?” is one of the questions that comes up when you Google her. Her reply: “I’ve never seen that! What the hell! I don’t know what’s worse—the idea that people are writing that with hope or fear? No, I’m not a Tory. Proudly not a Tory.”) The Waller-Bridge household was a hive of sociability. “There is and was always lots going on—music, chatting, laughing, people, and sharing bits of creative work with our parents and friends,” Isobel Waller-Bridge, Phoebe’s older sister, said. Her father, Michael, cofounded the first electronic stock market in Europe before moving into venture capital and reinventing himself as a portrait photographer. Her mother, Teresa, is an administrator at The Ironmongers’ Company, a 700-year-old guild in London. (They divorced when Phoebe was in her early 20s.) Waller-Bridge, who also has a younger brother, Jasper, is extremely close with her siblings. Isobel, a composer, wrote the music for Fleabag and, more recently, for a runway show for Alexander McQueen. “We do a lot of talking, almost casually—waiting for a bus, walking to the shop, making cups of tea,” Isobel said. “So it’s always part of our consciousness, and then often we’ll accidentally go down a rabbit hole for hours, and will usually come out the other side with something we’re excited about.”

For a while in her 20s, after graduating from the Royal Academy of Dramatic Arts, Waller-Bridge had a guinea pig–themed café of an acting career. She was temping, auditioning, getting no roles. “I think I felt like the most important thing was how I looked—especially in your 20s, when everyone’s like, ‘Cash in on it now because you haven’t got a lot of time!’ ” Waller-Bridge recalled. “Hair was everything.” Obviously, Waller-Bridge, as a beautiful, privately educated white woman, had a lot, practically everything, going for her; she has acknowledged that it is “absolutely probably true” that she had opportunities others didn’t. Still, the need to appear perfect kept her from accessing deeper forms of expression. “I had to remember how to be free,” she continued. “I was always trying to please, to do the right kind of acting.”