How to be Prettier: If you are a small person, you must carry a small bag. If you are big person, you can get away with a larger bag. Keep things in proportion.
How to be (less) Awkward: Instead of saying "thats dumb" or "she's stupid," try "silly." "Thats silly he dumped you for someone else." "What a silly girl to not know that." It seems less harsh and abrasive.