How to be Smarter: Wear a suit to work occasionally--it will make your boss think you are interviewing elsewhere, making you more desirable at your current job.
How to be Prettier: Wear the dress you like--not the one your date and your friends like. To paraphrase Hilary Duff, don't dress in yellow if you want to dress in gold.
How to be (less) Awkward: Please don't wall post what should be said in a facebook message. Especially because, sooner or later, your mom will be on facebook and WILL do the wall-to-wall between you and your boyfriend.