Basically I completely wiped on my rival in Pokemon: Sapphire right after the Houhou tower (whatever its called). Devastated, lost my starter and all the guys I cared about. All I had left was a Magikarp and a Zubat. Damn. But how I came to love that Zubat. When it turned into Crobat I was ecstatic! <3
I was able to slowly rebuild my team. But then half my team got wiped by a silly Sudowodo (who I didn't know was rock type, it looks like a plant!) and the deer pokemon (had some cheesy stomp move that critted everything). Damn.
Luckily I still had my Crobat and I forget if I had the magikarp from before or caught a new one. But I grinded and battled and made my way to the dragon gym. I was stupid and drunk and decided that my Gyarados with Ice Fang would be able to take out all the dragons even though he was a bit underleveled. I was half right. Then the gym leader threw out their highest level poke, Kingdra. FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF. Water + Dragon meant that the icefang wasn't super effective anymore. I wiped. Saddest week.