As for the silliest thing that's ever happened to me in game, well, this isn't strictly silly, but it's a story I laugh about heartily in hindsight. When I was a wee druid, at level 14, I got the quest for swim form. You needed to collect two halves to an amulet, both of which were underwater. The amulet's first half was at the bottom of the lake in Moonglade. Easy peasy, that's where you got the quest!
The amulet's second half was at the bottom of the sea off the northwestern coast of Westfall.
To get to Westfall from Moonglade at level 14 in Burning Crusade, you needed to do the following: fly to Rut'theran Village, take the boat to Menethil Harbor, run through the Wetlands (mobs were double your level), run through the pass to Loch Modan (patrolled by level ? Dragonmaw orcs), run through Loch Modan, run through Dun Morogh to Ironforge, take the tram to Stormwind, run through Elwynn, run through Westfall, and then locate the amulet half at the bottom of the sea, which was not marked. It also turned out that the item was beyond the max reach of your breath timer, and you needed to find a bubbling vent to regain your breath if you didn't want to drown. (I drowned.)
After hours - HOURS - of searching, I finally found the amulet half. In a euphoria, I hearthed back to Moonglade.
And realized I had not collected any of the flight points along the way.
What's the silliest thing you've done in WoW?