I am also wondering just how much of Chris's new found judgement and restraint regarding his Internet use has to do with Anna and / or other enablers /ass-patters. I'm willing to be that even Anna has her limits, and may just throw up her MANOS at some point and say 'fuck it'. I don't know about her, but I'd eventually grow weary of Chris's almost constant need for validation and general whining, pleading for advice, expecting people to fix his problems for him etc.
Anna may, at some point, find herself involved in a relationship with a significant other, leaving her less time for Chris. (It could happen.)
Not exactly sure where I'm trying to go with this, so I'll stop here.