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Some of these bonds are intended to take you into uncomfortable territory, it's true. But there's also a mechanical incentive for pursuing those, so I always recommend taking it as far as possible.
BondsI stole something from _______________.Tiernon has my back when things go wrong._______________ knows incriminating details about me.Brandon and I have a con running.
I don't have ideas for what, but I'm fine with either knowing incriminating details against you or having a con running. Brandon wouldn't do robbing, stealing and that side of illegal, but, like, selling supplies saying it's something it's not
I don't think he would on his own, but he could be roped into it.
I'd go for the "Tiernon has your back bond." As a hedge wizard, there was a time when Tiernon had dealings with Bug and may have helped him out of a scrape -- maybe rescuing him from a village and getting into trouble himself with the villagers for it.