Actually I've got a serious one. Usually when you tell the Stranger you've hurt someone you care about I get Kenny as an option because he's very easy to offend.
But I've noticed on some Let's Play Carley's name comes up, which I never get. Apparently you have to do something remotely hurtful to her for that to happen. Then on one play through Ben's name popped up and I'm like oh yeah, probably hurt him when I let him die in Crawford.
So I got to thinking, can you say you hurt Molly? It is possible to leave her behind at Crawford like Ben. And this can happen right after talking to her about her past. So I go through the whole game trying not to hurt Kenny or Ben and I left Carley behind in Macon so she wouldn't be considered an option.
So I get to Crawford, I'm nice to Molly about her sister, show that I care, then I shoot her, because, you know, I figured that was about as hurtful as Lee can get towards her (even if it is an accident). And for good measure, I lie to Clem about it when I get back.
I get to the Stranger, he asks me if I ever hurt anyone, I say Yes, and when he asks me who my options are Clementine, My Wife, and...Lilly.
Lilly?!?!? That psycho bitch? That doesn't even make sense since I never once did anything that suggested I cared about her on that playthrough. She get's a shout out in the I hurt people question, but not Molly if you leave her behind? What kind of shit is that?
Speaking of Lilly and the Stranger, if you say you've never hurt anyone you've cared about and sided with Kenny in the meat locker, he says "You didn't hurt that girl when you held her back while your friend smashed her father's head in?" To which I wanted to say. "Probably,
BUT I DIDN'T CARE ABOUT HER. So try again."