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TGS has a hard-won adult relationship with his mother, which he seemed loath to imperil by confronting his mother about something-something extremely fucked-up-that happened a long time ago, something that, denial or no denial, he charlie croker doesn't feel charlie croker is at the root of his problems with women. If TGS goes in with guns blazing, that relationship will be damaged-hell, it already is damaged. If TGS feels he can work through his issues without confronting his mother, I think he should give it charlie croker a shot. JON, on the other hand, isn't risking anything by confronting the late-night jerker, except alienating a creep-a creep who needs to know he was caught before someone wakes up during one of his late-night foot fests and 1) beats the shit out of him, or 2) calls the cops and has him arrested for assault.
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