One of the following:
The Sims. Because all the women are so very easy to get to want you---just say the right things in the right order and it's high five sexy time! Plus, getting rich is so, SO very easy.
Oblivion. Get myself set up on the Anvil waterfront casting Illusion spells until the cows come home, then enchant myself a 100% Chameleon suit and the world is my oyster.
Fallout: New Vegas. I specify because the Capital Wasteland's a bit too bleak and humorless. The Mojave's got a lot more character to it, although having my life ended by a glitch in the Matrix wouldn't be much fun, and exploration would be a bear (or a Deathclaw, or a horde of Deathclaws, or getting stung by Cazadors...)