Probably the most fun I've had being terrible at a game is with the battlefield series.
Remembering BF2, I was pretty excited to get this game (now that the price has come down slightly). After the unexpectedly long install time, even for a PC game, I jumped in to a march that was just starting and after 30 minutes of play time, I had killed one enemy, crashed several aircraft into buildings and been stabbed in the back repeatedly.
I thought about how I felt about the game vs the price as I reviewed my terrible score and realized I actually had fun anyway.

Knowing that BF2 took me some time to get the hang of, i know heilos and jets take plenty of practice to master. Since that first round I have gone on a few killing sprees and had a couple of heroic, tank-annihillating moments.

Im stil mostly a detriment to my team for now and nowhere as deadly as say, blackops, but for this first week of playing its been fun.

Same problems with gameplay from 2:
Teamates who grab up vehicles and leave you stranded in the desert,
Randomly spawning under the treads of an M1A1, forgetting which button you mapped your parachute to after bailing out of a burning heilo at 1,000 feet.

Same old fun,
New guns and toys, prettier scenery.