The silent treatment. Keep quiet and he’ll want to be the one to spill.
A good tease. Just don’t touch on a sensitive topic. Instead, rib him in a flattering way, like poking fun at his heartthrob days in high school whenever they had soirees. He won’t be able to resist your teasing.
Competition. Challenge him to a high-stakes game of Texas Hold ‘Em Poker and he’ll suddenly be endeared by you.