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  1. I'm wondering what kind of things you ladies wear on dates. It can be any kind of date, I just want answers. Even though I've never actually been on a date of any kind, as of this year I have been planning out what I would wear, and building a small wardrobe of date-worthy pieces (because I don't have many). I have a couple of skirts that are like this: Yes they are that short on me but I would be wearing shorts under there ( I would not wear a skirt of any length without safety shorts), but do you still think that would be inappropriate and send the wrong kind of message? I want to look cuter and different than I do on a regular basis (what can I say? I dress for comfort 99% of the time). If it were a date to someplace like the movies would you even wear a skirt/dress and heels? Would that look like trying to hard?