Elf

Starting off with F Scott Fitzgerald might not be the best for everyone, truly 

Considering that you like morally gray, flawed protagonists, you may want to try Wuthering Heights by Emily Bronte and if by the end you do not both love and want to throttle Heathcliffe i will be surprised

Wuthering Heights, in a nutshell, is a dark academia, doomed love story (which is honestly more obsession than love) and filled with antiheros 

One Hundred Years of Solitude is the best classic ive ever read. Its what reignited my obsession with reading and i will forever be grateful to it. Its very expansive and follows a singular family over a hundred years. Its magical realism too. Its, however got its set of trigger warnings so might want to search them up 

Jane Austen is also very accessible so any of her works would do.

Shirley Jackson is good! The Turn of the Screw, while I've not personally read it, is what The Haunting of Bly Manor (albeit loosely) is based on. So if you like horror (which, I'm assuming you do, because TMA) then both of those should be good for you!

The Picture of Dorian Gray is fabulous and if you can get past one of the later chapters which is basically a 7 page long inventory of the things Dorian possesses, it ends up being a very dark academia book with flawed protagonists and heavily gay undertones. 

Last but not least, On Earth We're Briefly Gorgeous by Ocean Vuong is not a classic but its got the same feel and language and style that most classics do and it is a stunning work of fiction so you could also start there. But again, trigger warnings.

I wouldn't say Charles Dickens or Maragret Atwood (definitely not maragret atwood for someone just starting out dear god) (im still scarred) or Dostoevsky or Hemingway or authors along those lines. They tend to have books more centred around themes and tend to be long drawn out and wordy 

What most people think about classics is that they are inherently boring and dry which just isn't true as proved by the books i listed. Some classics are even better plotted and more fun than modern day books; its all about finding the right one. That's why i sort of advice you to stay away from certain authors and books as well as they fall into a different genre of their own kind.

So sorry for how incredibly long this turned out to be 

If you have any more questions or want more info about any of the books listed, do PM me! 

Awesome! I think we own One Hundred Years of Solitude so I'll probably start reading that one! And I'll add to others to my TBR list! 

My other main bad experience with a classic was Great Expectations in 7th grade and it was just a nightmare. I'm sure Charles Dickens is a great author, just not to 13 year old me lol.  

Oooh! This wasn't intended for me but thank you!! We own a lot of those, and I've wanted to get more into classics. I will read them