When you fuck up something that's hard to fuck up.
Chris was really "pulling a Caleb" when he could barely walk across the room without falling over.
"accidentally" touching someone's boob while in conversation with them.
"sorry I think I just touched your boob"
"argh you're always pulling a Caleb"
Typically associated anytime the words "Why the fuck would he do that?" could be used.
Looks like Todd pulled a Caleb by inviting himself to our house and inviting his own friends too. What a piece of shit.
Pulling a Caleb does not make you many friends.
When you date two separate woman and you ruin them to the point where they end up dating each other.
Both his exes hate him so much! They’re together now! He's pulling a Caleb man!