I dunno; I think that the threshold for comment where Ian is actually sympathetic about Perry's situation is set too high. You need to have 8+ relationship with him, which effectively requires to never ever do anything that'd upset Perry. Otherwise you get the middle/neutral comment which covers whole range of 3-7 and is pretty meh:That part fits, he's only really snide when his relationship with Perry is very low.
Python:
if ian_perry > 7:
$ fian = "sad"
"I felt bad for Perry, but at least he had been true to himself. I hoped things wouldn't turn awkward between them from now on..."
elif ian_perry > 2:
"That sucked for Perry, but he knew he was fighting a lost cause. He played his cards terribly, and this was the result..."
else:
"Perry's self-centered ass got what was coming to him. Did he really think Emma would return his lame feelings?"