I had only an animal handling but it might be easier when PC has talk with animals skill. What worked for me: peaceful solution with owlbear mother, then met cub at gobbo's place and lost the chase but won dice rolls. Cub appeared at camp, at 1st interaction I haven't give it food directly, just threw. He ate meat and ran away. Then, after few nights he brought me some dead animal so I pretended to eat it. Cub was happy. Next time, I think, he showed up with wounds, nature+medicine check. When he arrived the last time I have pet it (don't remember if cub was happy about it and purred or not) and he went back to the forest. My advise is: be careful about petting cub as soon as he shows up at our camp. It's a wild animal after all, PC may end up with wounds.
