Jack Kerouac is primarily lauded for his keen understanding of male friendship. The female characters of On the Road or The Dharma Bums never really achieve the reader’s interest the way the males do. But Kerouac is also a writer of exquisitely sad love stories, with complex and fully realized women: The Subterraneans, Maggie Cassidy, and Tristessa. In these tales we find to our surprise that Kerouac was one of the most romantic of American novelists.
The most doomed of these three stories takes place in Mexico City, where Kerouac the narrator finds himself in love with a beautiful girl, an “Azteca, Indian girl with mysterious lidded Billie Holiday eyes.” The problem with this love affair is that she is addicted to “junk.” In some ways she is like the part of Mexico City that Kerouac experiences: sick, dangerous, and poor. But that appeals to the writer in him, and the potential redeemer. He doesn’t try to convince her to stop taking the drugs, but thinks perhaps his love alone can save her. This is a theme that echoes through the history of literature, profoundly romantic and profoundly foolish in the most tragic way. In Tristessa Kerouac brings that theme roaring into the modern age.
Jack himself, of course, is an addict, and he can understand her pain and joy. He says, “I wail on my cup of hiball so much they see I’m going to get drunk so they all permit me and beseech me to take a shot of morphine.” He does, diving in Tristessa’s paradoxical world. He tells us, “Tristessa is a junky and she goes about it skinny and carefree, where an American would be gloomy.” Then he immediately contradicts this and tells us that she complains all day. This complex girl, both magnet and poison, cannot be fathomed, much less rescued.
After leaving Mexico and living the adventures of The Dharma Bums, Kerouac returns to Tristessa, finding her shacked up with his friend Old Bull, a veteran addict himself. She is sicker than ever, and he knows he is too late to save her. She starts to hate him because he is not a junky, and he realizes that to love her he would have to become one. There is a third person in the love triangle, but it is not Old Bull, nor the Mexican “cats” so attracted to the waifish girl. No, the third side of the love triangle is morphine. Bull preaches the awful truth to Kerouac: “She don’t want love — You put Grace Kelly in this chair, Muckymuck’s morphine on that chair, Jack, I take the morphine, I no take the Grace Kelly.”
With this knowledge Kerouac leaves Mexico City, destined never to find true love. Was he not brave enough, as he claims? Was he unable to reconcile his romantic ideals with cruel reality? Or was he looking for love where it could not be found? We are left to wonder, and left to mourn, as Kerouac does, the loss of the unfathomable mystery of a young girl named, appropriately, Sorrow.