She creates conversations between opposing characters that, depending on your politics and preferences, irritate or seduce, as if one had wandered into a stylized art-house dream (or nightmare) with Socrates, Freddie Mercury and Virginia Woolf as hosts. “I am an evangelical transsexual,” she slyly jokes in one video. Wynn’s mission mirrors our technological, gender-restless, self-revealing culture. Her videos are as transparent as they are clever, tracking not only the evolution of Wynn’s ideas and production aesthetic but of her insecurities and transformation from a young man in a flannel shirt to a decked-out philosophical diva with hormone induced breasts and feminization surgery that reshaped her jawline and removed her Adam’s apple.

“It’s the big question mark in my life,” says Wynn, whose most recent video explores gender dysphoria, identity and beauty. “How do I handle the fact that I have two different gender identities that are immortalized on the internet? It’s what makes this channel so bizarre. I feel trapped sometimes by this old self I have represented online.

The whole process of transitioning is so difficult and awkward that I don’t watch my videos. Her earlier videos suggest a vulnerability while she navigated toward a moment of change.