personally , I think that Logan loved Rory more than she did him , just like Matt said . Otherwise , he would have not flown all across the ocean to surprise her . However , all he wanted was for her to say I want you , I choose you and she did not . Why does it matter if she loves him or not unless she shows it the way he needs her to show him . After being rejected once , I do believe that most people would not be that willing to throw it all away and let the other person know that they can stump over their heart again . Just like Lorelai , Rory is sort of a independent woman , the one that gets away and that you never forget , but Logan is not Chris and they are both at different period in their life so . just upsetting and heartbreaking and tragic and every other word along those lines .