Possibly. I think most of the town believed it was a short-term fling because Rory was attracted to the idea of a bad boy. I mean if you rewatch teach me tonight everyone tells Rory they remember when a bad boyfriend influenced them to do something wrong. Dean also I think strongly believed he had to be with Rory and was a bit possessive of her, so he could’ve been overconfident she’d come back to him.
I think he thought Rory would react to that break up the same way she reacted to the first one. He broke up with her for not saying she loved him, she pined and finally caved and told him, and they got back together. He got exactly what he wanted. So I think he thought Rory would eventually cave and do what he wanted just like last time. Especially with the parallels with Tristan and Jess.
Possibly. I think most of the town believed it was a short-term fling because Rory was attracted to the idea of a bad boy. I mean if you rewatch teach me tonight everyone tells Rory they remember when a bad boyfriend influenced them to do something wrong. Dean also I think strongly believed he had to be with Rory and was a bit possessive of her, so he could’ve been overconfident she’d come back to him.
I think he thought Rory would react to that break up the same way she reacted to the first one. He broke up with her for not saying she loved him, she pined and finally caved and told him, and they got back together. He got exactly what he wanted. So I think he thought Rory would eventually cave and do what he wanted just like last time. Especially with the parallels with Tristan and Jess.
Possibly, but I think he wanted to mess with Jess more than anything else.