In regards to looking for people where it says they'll be in the evenings: it won't just pop up on screen saying who's there, you have to go to the 'People' menu on the left side (Under Character, next to College) and it'll show a list of people nearby. If they're not there try waiting a little longer, usually by 8pm or so they'll be there.
In regards to the best friend thing: Visit the quad party every Friday and raise your party popularity by dancing, making out with other people, etc. It should trigger an event that will change your relationship with your BFF. If you've already tried that try hanging out with her platonically, but doing little things to raise her romance and lust meters (wear revealing clothing to the gym or arcade, pay for dates to the restaurant or movies, etc) and keep talking to her about sex every night.