Before we start getting into all of the many confusing aspects of Rory Gilmore's love life, we will say that we love Rory to bits. The entire Gilmore Girl series is a real masterpiece and that's largely due to how amazing Lorelai and Rory were both written and played. That being said, the more we rewatch this show, the harder it becomes to ignore all of the issues surrounding Rory and her many relationships. While Lorelai has her fair share of confusing romantic moments as well, like ignoring her feelings for Luke for over a decade, Rory has still got her beat.
Today, we will be looking back at all of Rory's relationships over the years and revealing the most confusing aspects about them. It really doesn't matter if we're team Jess, Dean or Logan, because in the end, none of their time with Rory made all that much sense.
15 Her Kiss-And-Run With Jess Was Mean To Everyone Involved
Let's head back to Sookie's wedding day for a moment. Putting Lorelai's issues that episode aside, we saw Rory plant a kiss on Jess (while she was still dating Dean, of course), tell him immediately not to say anything, then bolted and disappeared for the whole summer without a word. What did this accomplish other than hurt absolutely everyone?
14 Dead And Rory's 'I Love You' Breakup Didn't Make Sense And Went On For Way Too Long
This was an insanely frustrating storyline to get through. All it would have taken was a quick 2 minute convo to clear things up and everything would have been fine. It's not confusing that Rory wanted to wait before saying it back, but the breakup was dramatic and sent the whole town after Dean. All of that and then Rory just decided to say it. UGH!
13 Logan Shouldn't Have Been Blamed For Sleeping With Honor's Friends While He And Rory Were On A Break
If Rory had only been mad about how Honor's friends had treated her that day, we would have totally understood. They were the worst. However, to get mad enough at Logan to end things because he had been with a few of them during their break, wasn't right. Logan truly thought they were broken up. Who does she think she is, Rachel Green?
12 Rory's Quick To Accuse Logan Of Cheating, But She Clearly Doesn't Have A Problem Being The Other Woman
This is one of Rory's more confusing traits. She stayed mad for a long time about Logan hooking up with those girls during their break, but she's also proven time and time again that she doesn't really care about monogamy. She was fine being Dean's other woman and then was fine being Logan's during the revival! Not cool!
11 She Loved Jess From The Moment They Met, So Why Stay With Dean For So Long?
It was obvious that Jess and Rory were feeling each other pretty much the second he arrived in Stars Hollow. She would pretend she hated him, but constantly find ways to spend time with him. If she really didn't care for him, why go on that basket lunch? But she refused to break things off with Dean, even when she saw what it was doing to him.
10 Even After Choosing Jess, Rory Still Kept Dean Around!
For a smart girl, Rory really makes poor life choices. After the miserable public breakup that went down at the dance marathon, Rory was finally free to be happy with Jess and they were happy...for like a minute. However, Rory's need to keep Dean around as a friend was obviously going to ruin this. The winter carnival was so hard to watch.
9 Why Did She Think Going To Hang At Dean's Parent's House Would Be A Fun Date After She Ruined His Marriage?
The way Rory and Dean just assumed they could kick their romance off from where they had left it as teenagers was so weird. Dean was married and the way his wife found out about Rory was brutal. It's common sense that his parents wouldn't be huge fans of Rory's anymore, though it didn't seem to occurred to either of them.
8 Not That He Cared, But Rory Totally Used Robert
Rory is really painted out to be sweet and innocent with an excellent head on her shoulders, but the girl does have a conniving side. After Logan told her he didn't want a relationship, she showed up to a party with one of his best friends, obviously knowing it would be enough to get him to commit. Unfortunately for Robert, it totally worked.
7 She Really Didn't Understand Why Her Mom Was Mad When She Caught Her With Dean (Who Was Married)
It was never fun to watch these two fight. While Lorelai can be blamed for some of their tiffs, she was very much in the right during this specific one. Rory lost her v-card to Dean (while he was married) and got busted by her mom. When Lorelai rightfully expressed her disappointment, Rory snapped and accused her of ruining her special night!
6 Rory's Romances Eventually Eclipsed Everything She Had Been About At The Beginning
Originally, Rory's entire character revolved around her being a bright kid with the potential to do anything she wanted. However, as the show progressed, Rory seemed to push all of her goals and dreams aside to deal with her never-ending relationship dramas. Jess finally calling her out on this was one of the best scenes of the season.
