Why Rory? Why? - Comments

@Audrey T - Yes, yes to your points.
Dean was like the perfect first boyfriend, but when he cheated on his wife, c'mon that's not okay. And the fact that Rory was okay with it, I wasn't cool with that.
Jess was the dreamy boyfriend every girl wish she could date.
I agree, Logan had his own issues. But the things he did for Rory, like when he would drop everything for her.
I agree, now that I'm older and re-watching I can see why she turned him down. It makes more sense now.
I think this show also had an influence me wanting to become a reporter. Of course, I don't enjoy covering the politics, but Rory was a great reporter.
@Alex Moore - Yes, this is also part of my love for coffee!

I'm so happy there are others that have the Gilmore feels like me.

I followed Gilmore Girls all throughout my teen years. It was, by far, my favorite television show. (And I've been rewatching too!)

I think there was good things about all of Rory's boyfriends but then they all had a pretty fatal flaw too.

Dean was a great first boyfriend but he was endlessly jealous and insecure (and then later on he cheated on his wife to be with Rory which, I thought, was really shitty too.)

Logan could be a good boyfriend, but I always thought he had too many issues of his own to be a good boyfriend for anyone at the time. Like, I could see them getting back together ten years from the endpoint of Gilmore Girls and maybe it working out then. But I always felt like he was too fickle and never really, solidly settled his daddy-issues (something that almost always affected - negatively - his relationship with Rory). I thought that more than a few times he was just plain ol' hateful towards Rory (often because she was using her as an outlet for some other angst he was dealing with) and I just thought she deserved better.

When the show originally ended, I felt like you (like she could have had it all - Logan and her career included), but when I re-watched during college, I started to really see the bad in their relationship. I don't think she would have been able to fully go after her career dreams if she was still hitched to Logan. That boy requires so much attention and his family life comes with so many obligations, I think, without a doubt, that ultimately, Rory's career would have ended up on the back-burner, and Rory worked too hard to let that happen.

I think if she could have ended up with anyone (even if only for a little while), it could have been Jess. I think at the point in his life he was in when the show ended (he had his published career and he had pretty much gotten his shit together), he would have made a better match for Rory. I'm not sure if they would have lasted forever, but I think they would have been a good match for that stage in their lives.

(Oh my goodness, I constantly have so many Gilmore Girl feels.)

I need to go re-watch this! COFFEE!

But now that I'm re-watching, he wanted all or nothing. And I don't know how I feel anymore. God, it's sad.
But she follows her dreams. And that's all that matters.