Another vote for Gran Turismo 5.

I met up with ibmx2 ("Hi, Dude"!) one night and he gave me TONS of great advice and instructions, but I'm not very good so I just didn't have the talent to excel. That doesn't diminish the fact that I sure do enjoy it, but apparently the advanced stuff is beyond my skill level.

Also, I had regular weekly races with with a group of fellow newbies and we always had an absolute blast over the voice / video system. There was a lot of semi-serious competition... and encouragement... and joking around. LOTS OF FUN!