11/29/2023 0 Comments Stars hollow![]() ![]() However, this quickly digresses as his intellect and emotional maturity are not on par with Rory’s, often leaving him insecure. At the beginning of their relationship, he was somewhat of a decent first love for Rory as he was kind to her family, makes her thoughtful gifts, and is attentive. Right off the bat, his character is unsettling as he stalked her when he was trying to win her over. Not to mention that the financial difficulties she faced were all caused by her mother’s pridefulness.ĭean is arguably the worst of Rory’s boyfriends. Admittedly, she’s gone through a few breakups and faced some adversity due to her mother’s financial situation, but that is really it. This isn’t just her mother’s doing, this is everyone’s: her grandparents’, her town’s and her boyfriends’. Before Yale, Rory had never been confronted with discipline or realistic behavioral expectations. They taught her she could do no wrong her entire childhood. We think her trying to raise Rory as her friend instead of her daughter is very strange, and definitely contributed to her immaturity after she left for college, but we think Rory is coddled by all of Stars Hollow. It would be unnatural to start with anyone but our favorite mother-daughter duo! Although their relationship is problematic, and some may say unhealthy, we’re in agreement that Lorelai carries too much blame for Rory’s lack of morals, empathy, and overall likeability in later seasons.
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