How to be Smarter: The best site I've seen for online appointment booking and deals for spas and salons, customizable to your city. How to be Prettier: I find that most people don't wear heels everyday--it is just not practical. But most people tend to have lots more pairs of going out shoes than everyday shoes, so they have 6 choices of shoes to wear on a Saturday night but wear the same pair of flats everyday. Spend your money where it makes sense--on the everyday shoes you wear, not the ones that, while pretty, can only be worn once or twice a month.
How to be (less) Awkward: People that say things that are mean or have a biting tone tend to be because of their insecurities, rather than your failures. Instead of getting defensive, just say "ok," and be happy that you wouldn't trade your problems for theirs.