Hahaha! If we are going there some of my friends were Team Hobbit!
Agree that there is potential controversy in the question itself, as IK and others point out. But I decided not to take it that way but to explore the idea of pretty itself for me.
Here's the thing; I feel women often tell other women they look pretty in the same way we will say "You look thin!". It's an unspoken given in our culture that thin and pretty are always better than the alternatives. NOT here at YLF where people are more aware of different style goals and body positiveness, but Out There.
And often it is a generic compliment because let's face it, who is going to say "wow, you look like you could handle an apocalypse with ease!"
Let's say I was aiming to look truly androgynous and NOT pretty, and someone said to me, "You look pretty!".... I wouldn't be insulted but I wouldn't feel I'd accomplished my mission. On the other hand, if as Angie says, pretty can stretch all across the spectrum then how can I measure it?
Does anyone remember the episode of Seinfeld with the ugly baby that the hot male doctor calls "breathtaking", after calling Elaine the same thing, and she's all offended? Not only is pretty in the eyes of the beholder, but the MEANING of pretty as well - and that is where I suspect the disconnect arises.
MaryK, I feel you are the definition of pretty as YOU define it! Being a small Asian female means always being underestimated. And you inspire me to carry on and prove them all wrong.
Beth Ann, I am dying to hear more from you. I never thought of pretty as having an expiration date. Look at Jessica Tandy - pretty/beautiful always....
And Greyscale, can you ask your transgender friends that question? Have you read "She's Not There" by Jenny Finlan Boyle about transitioning as a middle aged college English professor, male to female? She talks about shopping for women's clothes and being just as dowdy (las a woman as she was when a guy... I kind of appreciated that perspective. Not everyone has to transition to Jessica Rabbit!