A phrase used by youtuber JackSucksAtLife and Rule 1 of Hacker Trolling
"You can't Diddle a diddle boy" or "Ya can't diddle a diddle boy" means
You can't troll a troll, or more specifically you cant troll the Diddle Boy; aka jack
*a staff member of Jack's tries to troll him on his mc server*
Jack: You cant diddle a diddle boy *cute laugh*
Play.skycade.net
12 step recovery jargon referring to someone new who talks about how great life is, now that they'resober. Usually meaning that the person is out of touch with reality.
The new guy seems pretty happy for a dude who has no job, no money and no family. He must be on a pink cloud.