Sarcasm is deceptively complex, agrees Elisabeth Camp, an associate professor at Rutgers University who studies the philosophy of language and mind. “There are all these issues [like]… social dynamics and power dynamics,” she said, labeling sarcasm as something “deeply, deeply human.”

It’s the context surrounding sarcasm that makes it function, Goodman and Camp explained. But for machines, that deep framework of past experiences and emotional subtext can be a stumbling block. Porting that level of knowledge into a bot requires far more than writing a few lines of snappy code, Goodman said. And it’s for this same reason we don’t often encounter bots that flirt or understand hyperbole.

Existing systems that marry comedy and artificial intelligence are somewhat effective, Goodman said, but rudimentary. “They usually work based on recognizing or generating very limited templates,” he explains. That’s why a bot might tell a “Yo’ Mama” joke one moment, but be utterly devoid of humor the next. Oren Tsur, a postdoctoral researcher at Harvard and Northeastern universities specializing in natural language processing and network science, built a sarcasm-seeking algorithm a few years back. The program could detect sarcasm in Amazon reviews and tweets, he said, but couldn’t quite banter. Instead, it learned to identify certain patterns in text.

Missy Cummings, an associate professor at MIT studying human interaction with systems, says sarcastic bots aren’t possible with today’s technology. “Robots [are still] having difficulty understanding very clear, distinct commands as opposed to nuanced differences based on sarcasm,” she said. A sarcastic robot is a “Holy Grail,” she explained. “You could do all the machine learning in the world on the spoken word, but sarcasm is often in tone and not in word,” she added. “[Or] facial expressions. Sarcasm has a lot of nonverbal cues.”

Cummings also notes—perhaps sardonically—engineers may not be the best equipped to decipher sarcasm and transform it into code: They require help from comedians. “We need to think more about how to make this a more collaborative process between a lot of different types of researchers,” she said.

It’s an idea John Lutz, the comedian who writes for Late Night with Seth Meyers and played 30 Rock’s dopey J.D. Lutz, is entirely open to. “I know the world is clamoring for the Lutz-bot 4000, and who am I to deny them,” he told me. Besides, Lutz notes, advanced artificial intelligence is already on primetime television. “I think Bill O’Reilly is doing a really nice job,” he said. (Were a computer to read Lutz’s quip, it would likely interpret the jape literally.) Comedian Keith Powell, who also starred on 30 Rock, says robots don’t need to learn sarcasm: They’ve nearly conquered the world already, and done a fine job stamping out interaction, human or otherwise. “I wait in line for coffee, and everyone is looking at their phones,” Powell said. “At this rate, robots will not need to discern sarcasm in conversations because there will simply be no conversations.”