He feels her shoulder's sag and he's guilty that his one experience with this is... is not great. He's not a good person, not at all, not like she thinks. And it's partially because of how he grew up.

"I grew up with people comin' an' goin' all the time. I wasn't allowed to get attached to 'em. Wasn't allowed to be sad about it after, either. What was the point, y'know? They was goin' anyay."

So he knows that maybe his advice isn't the best, when there was a constant flux and repositioning of slaves so they didn't have time to organize. He just didn't give a damn like he should at one point. He just wants to know Madoka will still be able to do that.

"You're pretty grown so I guess you got a good idea of you. But I still think it's okay to be a li'l' upset about it."