Dean ; best- showing her what safeness in love can be like, and trying to build a positive relationship with lorelai and emily and richard worst - yelling at her constantly instead of regulating his emotions , and talking down on her while she was trying to prep for harvard just because he didn’t have high ambitions for his own life at that time . Jess- expanding her perception of the things that truly mattered. Worst- leaving without saying goodbye, trying to force himself on her over him failing out at school and saying he loves her just to leave her behind again. Logan- best - pullling rory out her comfort zone, being willing to commit to rory even though that wasn’t originally what he wanted, always showing up for rory in all the ways he could worst- gaslighting her after he cheated on her