07/01/2014 08:41 pm ET Updated Feb 02, 2016

Trans Is the New Orange?

The second season of Orange Is the New Black just came out on Netflix, and I think we collectively inhaled it like a sugar-rimmed margarita on a humid summer day. Thirteen episodes of prison escapades straight into the veins. All I can say is #swoon.

Although her role in this season is minimal, I'm always happy to see Laverne Cox saunter onto my screen. Each time is a moment of celebration for trans-identified people everywhere, as well as for cis people who just love her. What has Laverne Cox taught us about ourselves? This savvy black trans woman appeared on one of this summer's Chelsea Lately episodes, and I found myself not listening to Laverne's answers but analyzing the depth and careful placement of Chelsea Handler's questions.

As we have seen in recent media mishaps concerning the hypersexualization of transgender women in interviews, it's not OK for interviewers to go for the easy "was a man, is now a woman" swipe. Hosts like Piers Morgan and Katie Couric had their mics handed to them after fumbling interviews with Laverne Cox and Janet Mock. Why am I bringing all this to light?

Well, part of it has to do with an overall curiosity about Chelsea Handler. Her latest book, Uganda Be Kidding Me, is one more installment in her funny-girl product collection, and in it she admits to wild spending on her cherished employees. In her new book she does this all while traveling through the exotic locales of Africa and revealing the many differences between First World and Third World vacation amenities. It's a little edgy, and Handler is clearly churning up all the puns, but I can't help cringing every time I glance upwards at the title bar atop each page. Uganda really sucks at handling LGBT issues, but really? Is the title a little insensitive? I don't want to, because I love Handler, but it makes me question whether America's irreverent and lovable comedy royal is really as race-, gender- and sex-sensitive as she tries to appear.

Whether she is sincere or not, I have to confess that the restraint with which Handler handled herself in the conversation with Cox was dripping with streetwise smarts and was quite frankly just crisply appraisable. Unlike Piers Morgan and Katie Couric (her first time around), she seemed to be educated on the verbiage, even leading Cox down the familiar interview lane of having to educate the audience while still having space to talk about herself. Handler was humble enough to admit that she didn't know which words to use all the time. She asked about "transgender" vs. "transsexual" and, from that angle, was even able to inquire (probably in the most politically correct interview of a trans person ever by a major network host) about whom Cox dates. "Jewish men," was her response, and that's where the real interview started.

If you didn't get the chance to see it, take a look for yourself. It's pretty classic.