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I'm not sure about Harold the bartender but for Logan the lumberjack it's absolately possible as I have him around 65 and 1 heart.

can you give me a hint on how i cant seem to progress him further

(1 edit)

There is not much to do to get his Like up. All I did was his jobs especially "a person to rent" buy drinks from him and I think staying with company also increases his attitude towards you. With the lumber jack I think it depends on what you chose during the bandit camo quest and werewolves.

thanks