Latest humor involves silly "opposite" scenarios like if it's raining and cold, or too late at night: "Hey mommy, let's go swimming!" Then I say, "Okay! Go get your swimming on. Let's go!" And she goes to pretend to get ready. It all started during our nightly "game time" and it was a game that I lost badly. It wasn't even close. But I announced, "Hey, it was SOOO close!" It took her quite a pause to figure out I was joking and to process the layers of the joke. Now we've branched out to using that humor in many situations. It's a step toward helping her understand nuances and take a step out of her literal world. The little game is fine with me for the meantime. It hasn't gotten on my nerves...yet.
Also, she's using some humor tactics to respond to the little jerk who plays friend one minute and bully the next=frenemy. The little jerk likes to say, "I'm not your friend" and wait for Little Squirrel to react with tears, then say, "I was just kidding!" over and over and over. All.day.long. Now when she says it, Little Squirrel says, "You're hilarious" or "Who cares?" with the perfect tone of voice (we had to role play it again and again). She seems to be feeling more confident now, finally, now that the school year is almost over!