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Gotcha - that first selfie icon is still grey on the end of the reunion report for me - but I do have the picture in the rewards/email section.

Ah that one, if you give Haily enough sexy photos she will send you her sexy photo

Ah, okay.  One last thing on this thread - I found that if you pick too many things to update Haily on, and don't select the "That's all" selection, the corruption won't trigger.  That might be intended, but I just wanted to mention it in case it wasn't.

Checking through I believe just some of the things you can say are a hard exit to the scene because of what they do the the girl.