Madonna isn’t always easy to love, even if you happen to really love her. But why should she be? She may not always give people what they want, but she reliably gives people what she wants, which is just as admirable. Her legacy at this point is untouchable—though her position in popular culture circa right now is a weirdly untenable one. Were she to abandon making new music and simply play the hits, she’d get called out for finally having become a nostalgia act. When she makes new music now—having already recorded a gazillion iconic singles—she gets shit for it, regardless of said music’s quality. Part of what infuriates people about Madonna is that, despite all of this, she remains unbowed. And this, of course, is why gay men love her.

Gay fandom is a complicated phenomenon and one, quite honestly, that I don’t always understand. But what Madonna means, particular for gay folks of a certain age, is something that is not to be taken lightly. These days it’s de rigueur for pop stars to support, embrace, and court a gay fanbase, but back in the '80s that was hardly the case. At a time when an entire generation was being lost to AIDS, Madonna was one of our biggest advocates. (She’s actually the first person I remember ever seeing utter the word "condom" on television, via her MTV safe sex PSAs) At a time when representations of gay people in mainstream media were few and far between, seeing Truth or Dare—a film that matter-of-factly depicts gay friendships in a way my teenage self had never before seen—was an unexpected lifeline. For a lot of gay kids who felt adrift in our secluded, pre-Internet teenage bedrooms, seeing Madonna cavorting with her gay dancers and actually celebrating their queerness felt like evidence that there was indeed a different kind of life out there for us—a club that might actually want us as a member.

I couldn’t stop thinking about all of these things while watching Madonna do a writhing version of "Like a Virgin" some 20 feet in front of me, a bizarro "I made it through the wilderness" moment that apparently a lot of the people in the room were also having. Aging along with your heroes is often weird. Some people—David Bowie, Patti Smith, for example—make it seem easy, cool even, while others (George Michael, I’m looking at you) make it really uncomfortable. For me, Madonna exists somewhere in the middle of those two extremes. Given that her whole career has been defined by pushing back against the status quo, it makes sense that she would continue to do so now. If she bristles at the mention of retirement (as she did when I talked to her), it’s totally understandable. People have been asking her about "aging gracefully" since she entered her thirties. Her career begs the question, at what point is anyone expected to give up doing what they love? And at what point is it considered necessary to give up on your idols and surrender to the tyranny of coolness?

As I get older, I increasingly hope the answer to those questions is never. Singing "Who’s That Girl" along with several thousand other gay men at the Montreal show proved to be surprisingly emotional for me, a rare instance of feeling part of some shared, mainstream gay experience. Watching Madonna medley her way back through the past three decades, I kept thinking about the guy in the lobby I’d seen earlier wearing a Keith Haring t-shirt and how Madonna herself had gotten choked up talking about Keith, as well as the countless other people who supported her career early on and were lost to AIDS. At some point during the show—maybe around the time she pulled out Erotica’s "Deeper and Deeper"—I scarcely noticed when my own cynicism about the whole thing evaporated while I danced. As a person who works in a culture that gleefully encourages snark and bitchiness and in which expressing admiration in a non-ironic way is often seen as a sign of weakness, it’s nice to be reminded how refreshing it is to simply love something because it makes you feel alive.

As Madonna neared the end of the show, it was nice to see that she too seemed genuinely moved by the feeling in the room. She gave up her tightly rehearsed performer posturing for a few minutes and simply became human, smiling and pausing to address the crowd. "Thank you so much for sticking with me all these years," she said. As me and my boyfriend started to drunkenly applaud, we were drowned out by the queen behind me who seemed to sum up everyone’s feelings by screaming out, "That’s right, bitch! Somehow we’re all still here. Aren’t we lucky?"