Dean
Dean Forester. The fairy tale first boyfriend. Dean set the bar for what a perfect boyfriend should be, and many guys have not met it. He was always there for Rory and was always doing the most romantic things. He even built her a car! But despite all of these Prince Charming qualities, he was still never the right guy for Rory. Rory's brilliance and drive were too much for his small-town personality, so Rory made the right decision by deciding to let this one get away.
Jess
Jess Mariano. The classic bad boy. His unpredictability always kept you on your toes, and it was a much more interesting relationship to watch than Rory's first one. His attitude of seeming to hate everyone besides Rory also seemed kind of cute (at first of course, then it just got kind of old). He may have had the brains to match Rory, but he definitely didn't have the drive. Rory was smart to finally let him go. Jess was more suited to be a close friend.
Logan
Logan Huntzberger. The rich and mysterious guy. He started off as being the worst. He was a lazy player who came from a family with money and was always getting into trouble. But somehow, he ended up falling for Rory. At times, he made her make the worst decisions; but he also helped push her out of her shell. Rory never seemed to have her head on straight while she was with him, so choosing her career over him was also the right choice to make.
The Final Verdict
The writers of the show made the right decision to have Rory end up with none of them. Although each of them had their good qualities, no guy was truly THE PERFECT match for Rory. They were each holding her back in one way or another. By choosing to pursue one of her dream career opportunities over a guy, she helped give the lesson that every teenage girl should know: always choose what's best for you over a guy. Fans are always disagreeing over which guy Rory should have ended up with, but I think they forget that the main point of the show is about a young mother raising a daughter on her own successfully. The show showcases strong and independent women, which is why it will remain a classic show for years to come.
