A lot of Chris' attachment to Tiffany Gowen comes from the association he made with her resembling Patti Mayonnaise from the Nick cartoon Doug. It's safe to assume Chris identified strongly with Doug and viewed his fictional crush Patti to be a symbolic sweetheart prophecy, animated just for him by a God who wants Chris to follow blatant clues right in front of his face to a guaranteed gift of female carnal love. It's funny that Chris acknowledged that he fucked up that clue and missed out on Tiffany. She was looking out for him in a motherly way though, like he was a little boy in her care.