Season 3
I have a feeling no matter what you option is in season 2- episode 5: kill Kenny or jane. I doesn't really matter, because telltale is going to screw your choice up somehow and piss us off. Like with Luke, Bonnie, Mike. I had feelings for them and they fucked them up. Now watch me have feelings for Jane or Kenny staying with me and they die a stupid gay way and I just say screw it idc what happens anymore... But hey that's just my 2 cents.
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