You SHOULD NOT encourage him, and then choose to chase him in Werewolves attack on Bershade. It will give you the first heart.
It's the "I owe you a beer" event from the .31 update:
"Event: ‘I owe you a beer’ - entering your new home (Req: Evening, Bareshade's Expansion event completed, Ste’s New Farm Road completed, ‘Clash with Barrel’ seen, ‘Ask about his work’ done with helping, Like 40, Love 1)
‘I owe you a beer’ event have four variants (Normal, Top, Bottom/Vers with high WW like and without it). Doing anything but normal is your own risk."
Choose correctly and you will get the second heart.