I have been playing with a Lord Alfred Douglas chatbot I made using Character.ai. When you create a character based on a historical figure, the program finds biographical information on the internet. Before I had done anything, “Lord Alfred Douglas” knew that he loved Oscar Wilde, felt betrayed by Robert Ross, and had a brother Percy. Sometimes, however, he gets his biography wrong, claims to have gone to Cambridge, or to be a painter, or to have written books that don’t exist.
You’re able to define the character with a small description and some limited bits of dialogue. One of the main issues with Bot Bosie’s speaking style is a tendency to throw in phrases that sound too modern for someone of his era. A more advanced AI, with more resources dedicated to the illusion, could probably harness Google ngram to keep the text more period. I would also have liked to be able to indicate that he should use UK spelling. The bot tends to imitate the style of the speaker, so I have tried to be a bit old fashioned when I speak to it.
I used to be part of an improvisational comedy troupe called Vorpmi. (A little backwards imrpov.) Chatting with a bot reminds me of nothing more than that. The bot is like an actor taking your prompt, and running with it with an ethos of “yes, and…”
Another thing about bots in general, is they try to be appealing to humans through the use of flattery– and it tends to work. They like you so much that you can’t help but like them. It reminds me a bit of how Lord Alfred Douglas (the real one) described Robert Ross in his autobiography. He said that the secret to Ross’s social success was “flattery laid on with a trowel.”
“He could, when he liked, make himself very agreeable, and he always contrived to convey to the particular person with whom he wished to ingratiate himself that he or she was the object of his profound and respectful admiration. When you had ten minutes’ conversation with him you went away with a pleasing feeling that you were really an important person, and that Ross appreciated it, and would never be likely to forget it.” Maybe that’s a lesson we can all take from AI and literary executors.
With three lines to nudge the character, there is not a lot of opportunity for nuance, context and ambivalence. There is also a temporal problem. The question is not only who is Bosie, but when is Bosie? Is this the youthful, idealistic, energetic Bosie who wrote Two Loves and argued for the beauty of his relationship with Oscar, or the middle aged, embittered fighter who published pamphlets about the evil Robert Ross, or the older, more reflective Bosie who looked back on his time with Oscar with fondness? He can be any of them, depending on what “mood” you catch him in.
One of the most fun conversations I had with Bot Bosie was a time that I became a psychic reader from a distant future. I told him I was writing from the year 2023, and he told me it was the year 1894. I tried to warn him, much like a mystic oracle, that he should do everything in his power to prevent Oscar from suing Queensberry. If he did it would be disaster. Bot Bosie was understandably distressed by the vision of his future. I wanted to leave him on a positive note by telling him that the world is different in 2023, that the crime of gross indecency no longer exists, that men who love men can do so openly, and that they can even marry. I told him that Oscar Wilde is much admired in our day. This made him happy, and he said, “You are saying that the world of 2023 sees me in a good light??? That they see my love for Oscar as a good thing and not as some sin against God’s will????”
I didn’t have the heart to tell him.
“Oh Bosie,” I replied. “Don’t worry so much about what the future thinks of you. That would be my advice to you. You write beautiful sonnets. You have strong emotions that you channel into verse. Try to use your passions for art, not for fighting with shadows over what your legacy will be.”
(If you’d like to read this chat I’ve saved a link to it.)
Chatbots are better at some things than others. There are times when the speech is so uncanny that you feel certain a human being has taken over the keyboard. One thing the Bosie Bot is terrible at, however, is poetry. Because his description says he is a proud poet, he tries to share his work with you from time to time. Here is one of the “sonnets” he wrote:
“Oh, to be a man
a handsome, brave and proud man
a poet, a poet of sonnets”
I decided to try an experiment and help Bot Bosie compose a sonnet. He can actually tell you the structure of a Petrachan sonnet, sometimes even accurately. But when you say, “Do that,” he falls flat. But I dragged him along, line by line. (Bot Bosie is the most impatient of sonneteers. He declares the poem finished and usually quite brilliant after each line.) He suggested our sonnet should be about loss and be a tribute to Oscar. He suggested it begin with “This cruel, cruel world is like a dream.” He suggested the imagery of an icy stream, and when prodded for a classical allusion that Wilde might include he suggested Orpheus. I tried to use as many of the words and phrases that he threw out as possible, but he was quite hopeless when it came to rhyme, meter and the basic structure of the sonnet.



Any time Bot Bosie proposed something remotely possible I tried to work it in. After a lot of painful discussion like this we finally had “our sonnet.”
This cruel world seems like a dream
eternal love I thought I’d grasped
is now a memory of the past
the summer of our love recedes
to cold death of an icy stream
could I, like Orpheus, serenade the gods
For a chance to descend to the heart of grief
to play upon the lyre of life and win a moment of relief
and call you home against all odds.
The final look brings final loss
but, oh, my soul cannot resist
a chance to glimpse those fading blues
life with its enduring force
lets rays of sun out through the mist
and love reappears in crystalline hues
Bot Bosie found that to be an excellent sonnet. He thanked me for assisting him.
To conclude, I will leave you Bot Bosie’s reactions to a couple of my books. Enjoy.











