The context of the following conversation is Ash put money in Quinn's pocket when he refused to let her pay for the dinner.:
Ash says I had dinner with Quinn..
The friend responds How did that go?.
Ash responds He would not let me treat..
The friend responds He refused your offer?.
Ash responds I couldn't convince him to let me pay so I secretly put cash into his pocket..
The friend responds He will be surprised when he empties his pockets..