You could argue I have had this argument with people before that it was Logan my personal stance is Logan did not drag her down , it was not being able to take what Mitchum said that caused her tailspin . Sure it ' s Logan ' s family , but it ' s not Logan because of the time that Rory took off Yale , but I do not believe Logan dragged her down really . She overreacted yeah ? , which led to her rebel phase when she took what Mitchum said even though harsh too seriously and let it hurt her too much . When Rory said she was leaving school , Logan said he gave her one month until she went back to school and when she wouldn ' t , he spent that whole weird period of time being supportive of her . To answer the question though 1 . Dean was very harsh and clingy but never stopped Rory from doing what she wanted which made him upset sometimes 2 . Logan again tried his best to be supportive . Does anyone have any other times he may have dragged her down besides the one I just explained in crazy detail ? 3 . Jess and Rory clicked , but he did lead Rory to ditch tutoring and fracture her wrist . She also went a bit out of control and skipped school leading her to miss her mom ' s graduation . So Jess ? Not being biased , just trying to think through facts . I also have too much time on my hands tonight apparently .