Once you get to the LLM judging them, you've given up, and might as well just prompt the LLM to make up funny item co-occurrences. Nothing wrong with giving up

Once you get to the LLM judging them, you've given up, and might as well just prompt the LLM to make up funny item co-occurrences. Nothing wrong with giving up though, it's a hard problem for all the same reasons recommendation engines are.