Let’s face it, Rory Gilmore’s love life was far from interesting throughout the span of seven seasons. She only had three real relationships, a few dates in between and then, of course, a few unfortunate men who tried to date her and failed. We’ve compiled a list of all Rory’s love interests, which includes relationships, blind dates and unrequited love and ranked them all from worst to best!
These two never really dated, but simply went on a date together. It was an arrangement set up by Emily Gilmore, Rory’s grandmother, so they were doomed from the start. Emily never has good judgement on what Rory needs when it comes to her love life. All she takes into consideration is their family linage and what their bank account balance is. Graham was initially really nice, but when he invited her to hang out later he took her to a sports bar where he proceeded to get drunk and be obnoxious with all of his friends. Rory was extremely uncomfortable and he showed no interest in actually getting to know her. This date ended wit her calling her married ex-boyfriend, Dean, to come pick her up and bail her out of this awful date.