Pokemon Ruby. I just beat the second gym leader, travelled to the route with the cycling road and I was stumped. I was supposed to get to the city with the 3rd gym leader but I didn't have a clue to how to get there. I wondered around, overleveled my pokemon team. Got bored, started a new game and got stuck at the same route again.
I was stuck at this point for literally a week. Then I was just running around aimlessly and then I found out you were able to go under the cycling road bridge. That may not seem like a big deal to you but in the previous pokemon games, you couldn't go under buildings and stuff so I had no idea. I got owned by a freaking bridge. A FREAKING BRIDGE. Not even Norman or Steven were as much as a pain as that bloody freaking bridge.