How to be Smarter: Whether you want to change careers within your current industry, break into a new industry, or just feel excited about your present job, I can't recommend the benefit of going to an industry conference more. Spending a day hearing from speakers, mingling with other inspiring people within the industry, and just breaking out of your day-to-day job routine to remind yourself of how many options there are within your career field is immensely helpful. How to be Prettier: Even if your date is being planned by the other person and is a surprise for you, it's okay to ask them what you should wear (jeans? a dress? something fancy?). In hot weather, also bring a light cardigan to account for indoor air-conditioning, and a pair of glasses if you need them for movie-watching, just in case.
How to be (less) Awkward: People that are appreciative are often the best-liked in their peer group. The quickest way to make someone feel appreciated is to simply say "thank you." In a note, in an email, outloud in the hall at school or work. I've heard people complain about not being appreciated, but I've never known anyone who complained about getting a genuine thank you from someone else.