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how do you get Logan's Heart if you don't encourage him?

You SHOULD NOT encourage him, and then choose to chase him in Werewolves attack on Bershade. It will give you the first heart. 

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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.