Photo courtesy Matt Peyton/Comedy Central

In the lead-up to Tuesday’s Season 3 premiere of Comedy Central’s Inside Amy Schumer, critics have been competing to lavish the show—which features Schumer in a winning mix of sketch, stand-up, and interview formats—with the most glowing praise. And with good reason. Schumer is one of the funniest comedians working, and her particular gift for sending-up sexist ridiculousness (from men and among women) is a joy to behold. My Slate colleague Amanda Hess identified the mechanics of this skill in her review: “Schumer’s sketches … resist the obvious target and find humor in surprise.”

Right on. So imagine my surprise when, in the premiere’s final interview segment called “Amy Goes Deep,” Schumer facilitated one of the most clumsy, contextually clueless, cringe-inducing exchanges on transgender issues I’ve ever witnessed—and this, after a period of trans emergence in the media during which someone of Schumer’s intelligence and curiosity should have learned to do better.

Before I jump into why it was such a blunt-force mess, I have to acknowledge that Bailey Jay, the self-identified transsexual who Schumer interviewed, seemed more or less fine with the often wildly invasive lines of questioning that the host pursued. I am definitely not here to tell Jay how to present herself or how to feel regarding the intense focus on the fact that, as Schumer puts it at the beginning of the segment, “you have a cock.” The thing is, Inside Amy Schumer is a hugely popular show (and ostensibly a progressively minded one at that) and it does not take place in a vacuum. Jay may be totally comfortable with prurient queries about her genitals and sex life, but that’s exactly the kind of scrutiny that the majority of trans women are fighting against.

The segment’s first and perhaps largest mistake was in not making clear that Bailey Jay is, among other things, a porn star rather than merely, as Schumer introduces her, a “transsexual.” That’s not to demean sex workers in any way, but only to point out that the perspective of someone who happily makes a living off the fetishization of her body probably doesn’t apply to most individuals. Presenting Jay as simply a trans person rather than a trans porn star is misleading in terms of what sort of experience the interview is trying to represent.

From that initial misstep, the segment stumbles down all the roads prominent trans voices like Laverne Cox and Janet Mock have patiently and not-so-patiently asked cisgender folks to avoid when discussing trans lives. “Did you ever think about snipping off … your penis?” Schumer asks with characteristic (and here tone-deaf) bravado, playing right into the genital fixation that is the bane of many trans people’s existence. And then, regarding Jay’s husband: “What was it like to watch him enter this situation. … I’m assuming he’d just been straight before?” To her credit, Jay quickly clarifies that her husband, being with a woman, remains straight, but Schumer has already reinforced the false connection between gender identity and sexual orientation that we all need to get past. Finally, there’s much talk of Jay’s being “gorgeous,” an interview theme that only makes sense if you are somehow working on the notion that trans people normally aren’t, and one that sets up a damaging division between those who have the resources, luck, and inclination to be conventionally attractive and “convincing” and those who don’t. Again, Jay does attempt to explain that her relatively positive life experience might be the result of an unfair beauty bias, but the interview editing and Schumer’s cavalier attitude cause any nuance to get muddled in innuendo that Joe Biden might enjoy women like Jay.

The most dispiriting thing about all this is that you get the feeling that Schumer wanted to do something good for the trans community with this segment—but unfortunately, the care and insight she typically brings to feminist issues just weren’t present here. At one point, she asks Jay “What do you think the biggest misconception is about someone who’s trans?” apparently not recognizing the painful irony that the very interview she’s conducted has trafficked in the worst of those misconceptions: that trans people are defined by their genitals and their sex lives, that their worth depends on their ability to “pass,” and that they should be comfortable discussing the most intimate aspects of their lives or risk being seen as unfunny or not cool.

Of course, you could argue that Schumer was deadpan dancing around all these pitfalls as a way of subverting them. But I am not convinced that the larger viewership is sophisticated enough on trans issues yet for that kind of subtle comedy (after this, I’m not even sure that Schumer herself is), nor do I think that this sort of segment allows for the nuance required in these discussions right now. For evidence of that, just look at the Daily Beast's Kevin Fallon, who called the exchange “the most illuminating interview with a trans woman that has ever aired on television.”* It’s true that the interview may have taught us something about Bailey Jay. But to imagine that it says anything about trans women more generally is absurd—and, worse, suggests that we are still in urgent need of reevaluating why, exactly, we want certain things “illuminated” in the first place.