Dearest Rory,
I have stopped myself from writing this letter a number of times because I don't want to do it. I don't want to have this talk, but since catching up with you, I can't help but have some things to say. I like you, Rory. I do. I did? I kind of do.
When we first met, I couldn't help but love your love of books. As an avid reader and writer myself, I found great joy in hearing you passionately talk about the books you were reading. I even put some on my own list after your recommendation. I thought your amazing relationship with your mom was admirable and was envious of your big part in the community of Stars Hollow. Sure, we disagreed sometimes. I found your taste in boys questionable and there were times when I thought you had to check your privilege but we got through it all. Then we parted ways and you came back 32 years old going on 13.
First of all, you're cheating on your boyfriend with a man whose proposal you turned down and is now engaged to another woman. There are so many wrongs in that sentence alone and yet whenever you have to say goodbye to Logan, you pout like you're the victim. I don't care if your current boyfriend doesn't like breakfast food (although I do find that absurd) and I don't care if you and Logan are in love, it could be written in the stars for all I care, you are a cheater, Rory Gilmore. And I can't excuse that.
The second topic of conversation is a little trickier. You're a freelance writer. I get that. I get that so much because I, too, am a freelance writer. I understand how hard it is to make it. I definitely understand how a few solid articles don't promise you a career. But this is the path we've chosen, right? The difference, Rory, is that if I were to have a website calling me nonstop, no matter how big or small, I would take the interview. And when I showed up to that interview, Rory, I would have been prepared. You actually threw a tantrum on the phone with the woman because she didn't give you the job. Did you really expect it after that disaster of a meeting? Remember when I told you that sometimes you have to check your privilege? This is one of those times.
Oh and remember when you decided to be bold and take that piece about lines in New York City? I was proud of you. That's the Rory who doesn't sit around and wait. Except then you fell asleep in the middle of an interview. I don't care how tired you are. We're all tired, Rory. Aren't you the one who has coffee running through her veins? Drink a gallon and do your job.
I guess what I'm trying to say is that I'm disappointed in you. I'm not disappointed that you're back in Stars Hollow. I'm not disappointed that you don't have a killer career and I'm not disappointed that you're single. I am literally in the same boat as you, Rory. I am living in my hometown with a job that is far from my dream and I am single. The difference is you. I complain. We all complain. But you have decided to make a bed out of your complaints to sleep in.
Rory, when I first met you, I found you unstoppable. You were passionate and intelligent and determined. You were also kind and understanding. When you decided to write a book, I cheered victoriously for you... Then your mom told you she was uncomfortable with the idea and you stomped your feet in a cemetery. The mother who has literally been your day one and has given you everything she could possibly give and that's how you treat her. And to apologize, you offer ice cream from her own freezer and tell her you wrote three chapters anyway.
I've been lost before. A lot of people have. And you have every right to be lost, confused, angry, and frustrated. I just wish you could remember the girl before the Yale diploma and "The New Yorker" article... Because it seems like you believe that that girl deserves to be handed the best when she only became that girl because of the grounded and hard-working Rory I once knew. That girl deserves better. I hope one day you wake up and realize it.
Oh, and you're still a cheater.
