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Actually I want to know what you haven't done with him. But you can check in Relationship logs instead. Like this

Oh. I've done everything, its all ticked off and belly fun option isnt even there

The requirement for this event is Bandit's camp morale more than 25, and in Northcrest quest, you need to do in the green way which Bandit's camp doesn't get rid.

Morale is like 43 and I did do that during the Northcrest quest

That kinda weird, if you ever have sex with him by rent him a night and got enough like, there should be Belly fun in conversation to talk.

How do I get his like up more?

Have you tried to help him work at his bar or rent him a night (ask him to accompany when you rent him a room)?

Yes, I've rented him out a few times. His current like is 35

I think you have enough like for him. If you said you have camp's moral (not Bandit affection, it's not the same thing) more than 25 and Green ending in Northcrest conspiracy event, there should be Belly fun appear in talk option.

Bandit camp morale is 90, I have the green ending on the Northcrest Conspiracy, Harold at 35 like and. . .no belly fun option even after sleeping with him again. I'm so confused

I just noticed, your Like for Harold is 48, mine is permanently stuck at 35

If I remember correctly, I got his like for some event like Rat's problem and some from repeatable event with him. But I'm not sure how much each.

I guess all I can do is keep trying? I mean, I did Rat Problem and I'm doing entertaining guests but it doesn't seem to budge. . .