Gameboy, I've never held a Game Gear I guess.
Nathan Drake or Ezio Auditore?

Ezio. He's cool without trying too hard.

G1 Transformers or G1 GI Joe?

Transformers

Halo or CoD?

20 million now because I could just put it in the bank and make 400k in interest every year.

Simpsons or Family Guy?

OMG, are you serious? Do I really need to answer that?

being single or taken?

Hmmm...single, because it's more fun.

Bear Grylls or Ray Mears?

Hamburgers, love em both though.

Orange juice or Apple juice?

most time orange juice but sometimes i like apple juice more^^

5 years normal sex life or 1k dollars every month for 5 years without sex

Apple juice because it is tastier and more refreshing.

EDIT: Your question doesnt make sense... Anyway, I choose 1k dollors for 5 years.

EDIT 2: I choose normal sex life for 5 years because $1k isnt alot of money.

Herpes or Gonorrhea?

too late mate