Hey now, what do you have against the hobo. He ain't fucking anyone's girlfriend (much to Joshy92's chagrinAs for the second, even though that happened on every path, Joey would still be competing against Chris, the hobo, the bar customer, some more random sleazy dudes, and above all BEN. He can still be safely be given the award of "Most decent male character in Long Story Short."
I'm also not sure about Chris -- aren't all his dealings with MC basically upfront? I don't play the NTR path so i don't know, is he aware if MC tells Ann that he wants her to stop seeing him?