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Why did Dean have to tell Rory he proposed to Lindsay?

General Discussion

I know this has probably been discussed to death, but I'm doing my yearly rewatching of the show and found myself puzzled. Warning, early morning nonsensical ramblings below!

The timing of his proposal was off, considering the night or two before he started a fight with Jess over Rory - especially not actually knowing the reasoning behind her being upset.

Did he actually love Lindsay? Why did he feel the need to tell Rory? Was he wanting her to object and beg for him back in some tragic epiphany? Why was he angry at her reaction even though he's all top aware of how she views the importance of studying/future/college?

All in all I'm not a fan of Dean in the slightest, but i still question the mentality and motives behind telling her.

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Thinking Snoo

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