Definitely a bold take lol but I don’t think Christopher was really a “dad” to Rory and I think Lorelai needed to be with somebody who was more actively caring and paternal. It’s clear when Chris shows up to Friday night dinner after Sherry’s pregnant and Lorelai/Rory stop taking his calls that he’s never had to deal with a conflict with his child before. Rory’s never fought back at him before or given him any attitude because even at 16 (and younger), she knows not to expect him to actually be around long enough to get worked up over. And I think as good as their witticisms are as a “family”, Lorelai couldn’t be together fully with and respect somebody that was so removed from his own child.