Shane Michael Singh

In his Twitter profile, Shane Michael Singh wonders if “celibate gay Playboy editor” is enough of a pitch to get him a book deal. It’s definitely not the expected profile of a man in his position. But he and a team of young Millennials are reinventing the iconic brand and may be shifting the idea of a certain kind of masculinity along with it. When he asks What the Future, he’s wondering if men feel like they’re part of the conversation about the future of gender.

Before you get a moment to breath in Ariana Grande’s fourth studio album, the moving and mature Sweetener, she cuts you deep with soprano notes of tragedy. Titled “raindrops (an angel cried),” this opener—a soaring and cathartic 37-second eulogy—courageously sets up Sweetener as an antidote to suffering.

Before Bruce Jenner sat down with Diane Sawyer, before Laverne Cox earned an Emmy nod for Orange Is the New Black and before President Barack Obama appointed the first transgender woman to a senior government position, there was Tula. A striking six-foot-tall British model whose face graced magazine covers and popped up in national ad campaigns for vodka and lingerie in the 1970s, Caroline “Tula” Cossey never yearned to be more than a working model and, someday, a wife.