hello. i'm about the same too, always dunnoe where to go.. so
here's what i usually do with my buddies.
1. mt faber, it's very nice up there, very relaxing.
2. geylang, many interesting stuffs there... good food too!
3. changi village? even more interesting stuffs. no food, got
7-11.
4. sentosa.. need to pay to get in.. strange though... that time
security guard wanted me to pay and its 3am in the morning!
5. try taking a walk at those cemeteries at lim chu kang... might
see something extra! 
for supper/drinks
1. s11 at fort canning.. see cars vroom vroom..
2. simpang bedok.. prata, nasi lemak~
3. La Salle a Manger cafe at paya lebar, opens till 2am
4. one fullerton, lotsa cafe. embassy is really cool!
5. jalan kayu, prata again~
does anyone know how to get into the marina sq area where you can
see the city view of esplanade and the merlion? there's always
filming there but i'm not sure where to enter from.
