Rory Gilmore goes a long way over the course of the original Gilmore Girls series. The pilot episode sees her as a fresh-faced student, about to head off to Chilton and get the best education she can, so that she can go to Harvard and become a journalist. Of course, not everything goes to plan.
Instead of Harvard, Rory ends up at Yale (by choice), drops out, goes back, and then does manage to end the series about to go cover Barak Obama's campaign trail. It's a fantastic end, that seems like all her dreams are coming true. However, in the revival (A Year In The Life), Rory is seen floundering. If that young Ms Gilmore from episode one saw where she ended up, what would she love (and what would she hate) about her future self?
Hate: Being Broke
Rory declares that she is 'broke' in the revival - and she's also technically homeless, as she gave up her New York apartment to couch surf while she tried to figure things out. (A fact that utterly appalls her grandmother, but which makes a certain amount of sense - New York is expensive!) This might not be a rarity for college graduates, but first episode Rory would no doubt be shocked that her future self isn't more financially secure.
Proud Of: Still Connected To Her Hometown
Rory has always had an amazing connection to Stars Hollow, and makes no secret of the fact that she adores it and always takes part in the town's various madcap festivals and events. The town's sendoff for her in the finale proves that they feel the same, and while she no longer lives there full time in the revival, she's still deeply connected to the place and the people there.
Hate: How Little She Sees Lane
In the first season of Gilmore Girls, Rory and Lane are absolute #BFFGoals. They both have big dreams, and are ready to go off and conquer the world, Rory as a journalist, and Lane as a rock star. By the revival, though, they rarely seem to see each other. They are still friends, of course - Rory comes to stay, and keeps some of her 'boxes' at Lane's place, but they also reference how much they need to catch up, and how little they see each other.
Proud Of: Wrote For The New Yorker
At the start of the revival, it seems like Rory does have her life together - and everyone in town is incredibly proud of the fact that she wrote for the New Yorker!
This is a long-time dream of hers, and Luke even laminates the article for the back of his menus. No matter what happens with the rest of her career, Rory would be incredibly proud of herself for this achievement (as she should be).
Hate: Lack Of Direction
Of course, her article for the New Yorker seems to be the pinnacle of her career achievements, and the rest of the revival sees her struggling. She tries to take on an article for Conde Nast, but fails to really connect to the subject matter, she tries to write a book with a celebrity, but that relationship crashes and burns, and she thinks she may get a staff writer job with a website, but tanks the interview. Season one Rory was incredibly driven and sure of her path, she would hate to see how that has changed.
Proud Of: Keeping The Stars Hollow Gazette Alive
As Rory struggles to find work, she discovers that the Stars Hollow Gazette is going to go under - and takes on the (unpaid) job of editing it. It's far from an ideal situation, but she does it out of love for the paper that she grew up reading, and her younger self would be thrilled that she was keeping it alive. (Possibly less thrilled about her taking the job for no pay, though.)
Hate: Wookie Sex/Forgotten Paul
Rory was always a romantic, and while she struggled with staying monogamous (cheating on Dean, with Dean, with Jess, and eventually, with Logan), she wanted to find a great, loving relationship and stick with it.
However, in the revival, she is definitely failing to do that - she has a boyfriend that she continually forgets about (and cheats on with multiple people, no surprise!), and she has a one-night stand with a stranger in a Wookie costume that she immediately regrets. To be fair, revival Rory is unimpressed with these decisions too.
Proud Of: Never Settling In A Bad Relationship
Rory may be a romantic, but she's not willing to sacrifice herself in order to be in a relationship. From the start, she refuses to be pushed in relationships - whether that is not being pressured into telling Dean she loves him, calling Jess out on his behavior, or turning down Logan's proposal when she feels like she's just not ready. She would be happy to see that no matter what, she refused to settle.
Hate: Having An Affair With Logan
One of the most contentious aspects of revival Rory was her ongoing affair with Logan. It was not explained exactly how this one came about, but Rory and Logan were definitely having an ongoing relationship, despite the fact that he was in a serious relationship (and his partner moved in with him). Rory does end it, eventually, but there's little doubt that her younger self would have been seriously judgemental about this one.
Proud Of: Still Having An Amazing Relationship With Lorelai
And of course, at the heart of it all is the relationship between Rory and Lorelai. Despite their ups and downs, the time they didn't speak because Rory dropped out of school, their occasional fights... Rory and Lorelai have one of the closest mother/daughter relationships on TV. Young Rory would probably forgive her older self everything, as long as she stayed close to her mom, and while they don't get to spend quite as much time talking as either would like, they are just as much besties as they ever were.