Hahahahaha, you know what dude? Dont you think I say that to myself everytime I put on makeup? If only I could have the makeup on permanently, we would all be in heaven.
For myself, having makeup on definitely increases my confidence, by .........ALOT!!! Im almost a completely different person.
Well even if their is waterproof makeup, I wouldnt have it on all the time, cause I would never sleep with makeup on. Its bad, you need your skin to breathe.
Mystikins, have you tried those mineral makeups? Like Jane Iredale, or Bare Escentuals. I think they're supposed to be waterproof. They can be kind of expensive though. I've tried Jane Iredale, and it was okay, but it settle into the fine lines under my eyes.
Another is Clinique Almost Makeup. It's sheer, so you might need to dab concealer on a couple spots, but it is waterproof, and it also has SPF 15, which you'll need anyways. I've never tried it, but I hear its good.
I hope this helps, and I hope you have a fun summer!