Anna's was difficult, so let me know if you think any were wrong. Overall, I think Anna would value a sense of romance/adventure but also fun and loyalty. I think she'd prefer princesses who are more like her, but in the movie she seemed to want to be more graceful (if you remember that funny part in FTFTIF) and of course, family is a huge priority to Anna.
Thanks a lot to all of you who gave me list ideas for this (especially Silverrose for the descriptions). Also, huge thank you to the then-fanpoppers princesslullaby and co. for originally doing this idea and inspiring me. I don't agree with all their rankings but I loved those articles so much (google "fanpop princesslullaby favorite princess list" and some will come up).
Tiana doesn't care about magic or romance, so Anna wouldn't find a princess as realistic and grounded as she is particularly engaging, nor would she care about Tia's dream of her restaurant. Anna would like her determination and loyalty to her family, and probably like the scenes where she sasses Naveen, like in some of Anna's scenes, but otherwise find her uninteresting.
Anna would have mixed feelings about Rapunzel. On one hand, she'd love Rapunzel's quirky, sweet, naive, funny personality. She'd find her easy to relate to personality wise and admire her optimism and how she tries to be more take-charge. She'd LOVE the pub scene and dance scene, where Rapunzel inspires others. But Anna would find Rapunzel a little too rebellious, because she would relate Gothel's hiding them both away for protection with Elsa's ignoring Anna for years. Anna never left or gave up on Elsa, so she would find her decision to deliberately hurt her mother by leaving shocking.
Anna would find what Merida cruel for what she did to her mom and her general personality a bit harsh, but she would cut her some slack for trying to fix her mistake. Other than that, though, she wouldn't find Merida very admirable, but like that she's so spirited and always has adventures.
Anna wouldn't blame her for taking the one chance she has at becoming human, because Anna would connect it with how she took her chance at finding true love at the party. She'd love Ariel's romantic, adventurous side, relate to the mistakes she makes, and like how she never gives up. However, she'd find Ariel a little cruel to leave her father and sisters, though, since family is important to Anna.
Anna would admire Belle trading her freedom for her father's. She'd relate to her loneliness and wanting to meet someone like her. But Anna doesn't care about intellectual pursuits and would find it hard to identify with Belle's cultured, somewhat cold personality.
Anna would like how Mulan, like Anna, is clumsy, a bit naive, and determined, loyal to her family and never gives up even when she has a chance to. She would find her scenes trying to act like a man really funny and think Mulan is heroic. She wouldn't really connect with Mulan's not knowing who she is, but she would admire how she goes out of her way for her family and relate to liking a grouchy, serious guy ;) However, she'd still find Mulan a little too serious and unromantic for her taste.
Anna would love how Cinderella takes a big chance at finding happiness at the ball at the first opportunity she gets. She'd like Cinderella's romantic side, sense of humor, and that she remains humble and compassionate after years of abuse. Anna would acknowledge Cindy as a good role model and love her for beating the odds, but want a more playful heroine.
Anna would admire how Jasmine lets no one walk over her, her quick wit, that she takes matters into her own hands, always tries her best, and how she is sweet and sassy at the same time. She'd love
how she is a romantic who wants to see things and meet people. She would love the instant connection between Jasmine and Aladdin and how forgiving Jasmine is. But Anna would see Jasmine as a little too unkind and judgmental at times when she should be polite and kind to people.
Anna would like Aurora's wit, her free spirit, and how she's so sure she'll meet the man in her dreams someday. She'd love how elegant she is because Anna would like being more that way. Anna would love that she finds romance by pure happenstance, love the romantic scenes between Aurora and Philip, and how she interacts with the animals adorable. She'd also relate a lot to how she yearns for romantic company and wanted to get to know Phillip better.
Anna makes decisions easily where Pocahontas does not, and Anna is more concerned with family and love than finding her destiny, so she wouldn't really connect in that regard. However, she would like how Pocahontas is wild, playful, and loves animals. Anna would like how she also tries to be mature and strong for her people, but is also a daredevil who isn't afraid to take risks. She would be sad Pocahontas let John go, but admire her strength. Anna wouldn't dislike anything about her.
1. Snow White.
Anna would love everything
about Snow White: her deeply romantic, idealistic, spunky personality, her cute scenes with the Prince, and find her really funny. She'd strongly relate to her wanting to be loved badly after being alone for so long, being so sheltered, and probably equate Snow White's domineering the dwarfs' house with getting Kristoff to do things her way. Anna wouldn't find Snow White stupid for believing the apple would make her dream come true; she'd understand why she did it. She would like how Snow manages to be both really fun and child-like, while also graceful. She would see her as a role model for her generous nature, her optimism, and her ability to love and be loved after an unhappy childhood.
Next is... Elsa!
Also planning to do many of the non-Princesses' lists. If you have ideas on them, message me!