My memories of My Fair Lady were of an exuberant show that propelled me, at age 17, breathlessly through senior spring: Kelly Pavlak dancing all night, Mike Marier swinging on lamp-posts, Jon Richter getting dressed for the ball and Amy O’Gorman for the races—and me, as Col. Pickering, jumping on an armchair during “The Rain in Spain” to win five dollars from Kelly’s dad in a bet. All this happened while, it seemed, 12 grades’ worth of students looked up in awe at us: grown and sophisticated, ready to take on the world beyond our little Catholic school in St. Paul.

When I recently saw My Fair Lady at the Guthrie Theater—my first time seeing the show since high school—I was surprised at how bleak it actually is. The transcendent songs are all there, but they have layers of cynicism and irony that were largely lost to me as a bright-eyed teen attending a high school where traditional gender roles were seen as what God intended. At St. Agnes, a lot of Higgins’s misogyny—cartoonishly exaggerated even by mid-century standards—played as simply Men Are From Mars, Women Are From Venus.

In high school, I’d also never been in a relationship—even a teenage fling—and so the dynamics of resentment and manipulation that play out in the musical taken from George Bernard Shaw’s Pygmalion were as foreign to me as the drunkenness I’d tried to ape when I played Tevya hitting the samovar in an earlier high school show. As a teenager, I saw the daringly ambiguous, almost anticlimactic, closing scene of My Fair Lady as simply a happy ending. Now, the whole show seems not so much misogynist as outright misanthropist: the virtuous are punished, and the wicked are rewarded.

I was cast as Pickering, I assumed, because I was a confident actor who couldn’t carry a tune. (I had to argue for the right to actually sing during “The Rain in Spain,” my character’s one song, instead of lip-synching.) That probably explains it as far as the casting director was concerned, but watching Pickering from the outside, I saw how uncanny my casting as the doddering linguist was. Pickering’s was the role I played with girls and women in real life for years: always the friend, always the protector and supporter, never the lover.

In the musical, Pickering is removed from the romantic equation simply by being an old man—but his character’s impotence is about more than a lack of Viagra. Though he’s a little insensitive at times, he’s a paragon of gentlemanly virtue in comparison to the musical’s other two characters: the cruel Higgins and Eliza’s philandering dad.

Eliza says as much to Higgins’s mother: “I should never have known how ladies and gentlemen behave if it hadn’t been for Col. Pickering. He showed me that he felt and thought about me as if I were something better than a common flower girl. You see, Mrs. Higgins, the difference between a lady and a flower girl isn’t how she behaves, but how she is treated. I’ll always be a flower girl to Professor Higgins, because he always treats me as a flower girl and always will. I’ll always be a lady to Col. Pickering, because he always treats me as a lady and always will.”

In a cunning twist by the playwright, though, the most savage tirade against the mistreatment of women comes from Higgins himself, who’s perversely convinced that the meek Freddy—Eliza’s besotted suitor—will turn into an abusive monster once Eliza’s married him. In other words, cautions Higgins, men are dangerously manipulative. Professor, heal thyself.

And yet, who gets the girl in the end? Spoiler: it’s not Col. Pickering.

Eventually, in my own life, I did enter the romantic fray, and I’m now in a happy relationship. It’s tempting to think of my life story as Pickering’s revenge: to think that I’ve remained the guy whose yearbook is adorned with bubbly cursive reading, “Stay sweet!”

I certainly don’t think I’ve turned into an asshole, but what makes My Fair Lady feel far less comfortable than most musicals is the suggestion that everyone thinks of himself as the Nice Guy. We don’t meet any of Pickering’s lovers, but it’s easy to imagine a Higgins-like scene playing out back in Pickering’s office in colonial India, with a woman (or man) storming off into the arms of a South Asian Freddie after tiring of this mustachioed scholar who thinks he knows everything.

My Fair Lady is one of the most beloved musicals of all time, but it’s also a kind of poison pill. Is that why the world continues to love it—as Eliza continues to love the condescending, charismatic Higgins? Or do we love My Fair Lady because of Pickering: the character who gives us an out, who can convince us that Shaw, Lerner, and Loewe knew how true ladies and gentlemen behave? Is Pickering a wimp—or a wink?

As for me, I don’t know if I’m still a Pickering…or if I ever really was. I do hope, though, that I still know enough to sing a song when it’s given to me—and to jump on the furniture a little bit while I’m at it.

– Jay Gabler