Rory Gilmore-Hayden has a wonderful life with a steady job,crazy friends and a wonderful mom and dad who adores had everything she had almost achieved everything she had dreamed of. She is living in Hartford and is a features reporter at Hartford Gazette. Everyone who knows her loves her and are surprised by her achievements at such tender age.
The only thing she is lacking is a boyfriend, it's not like boy's are not interested in her. Most of the guys see her as rich heiress and try to take advantage of her. That's the reason she is very picky in boyfriend department. She dated a few guys but the relationship didn't. She is having these troubles since her big break-up with Tristan Dugrey during his graduation.
They were together since their chilton years and broke up in her senior Chilton year when he cheated on her. They parted their ways by Rory going to Yale and Tristan going to Harvard. After a year and half, Tristan came back to her apologised and begged her to take her back. She took him back after consulting her mom for advice. She forgave him and they started dating again. Even though it was long distance relationship it went well, in her senior year at Yale Tristan proposed and she said 'Yes' to parents and both set of her grandparents were ecstatic about this wedding. This was supposed to be the biggest society event of the year. But all this came crashing down when she visited Harvard for his graduation, she came to know about his bed-bunnies in Harvard.
She broke with him and the wedding was called off. It took her six months to recover from the break-up. She resumed her normal life and got a job at a local paper. After two years of working her ass over there, she finally got a job at Hartford Gazette,the best paper in the State of Connecticut. She loved working there, since it is close to both Hayden's and Gilmore grandparents:it is even close to Starshollow where Christopher and Lorelai lived since Rory was born. She loved everything about the town and tried to lead a normal life in that town even though she was rich.
She is working at the Gazette since three years and had won some journalism awards and is living with Paris who is practising medicine at a clinic in Hartford. She was setup by Emily and Francine a lot of times by different boys in the last five years hoping that she may find the one but in vain.