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[GreatWyrmGold]

Recently, I lost my fortress to invaders for the first time.
They were kobolds. Granted, this was after a necromancer sent a few undead which killed a bunch of dwarves, and before I could get past my aquifer, AND they sent a squad of bowbolds and one of spearbolds, compared to my lack of a militia at all, but still...kobolds.

What's something embarassing that's happened to your fortress?

[ClkWrkJester]

The fort I reclaimed 14 times.

5 aquifer accidents.
4 croc attacks.
1 -named- croc attack.
2 sieges.
1 time forgetting to bring food.
And finally the most badass kobold thief in history.

[NRDL]

My two person military, both armed with crappy copper short swords, and with only novice in swordsmanship and dabbling in a lot of other stuff, were wiped out by a single goblin thief with a knife.

This triggered a tantrum spiral.  I'm starting to guess that the goblin was an anarchist, sent to soften up a fort before the sieges and ambushes were sent.  True enough, a few seasons later, a siege shows up. 

[Urist McScoopbeard]

Accidently flooded my own smithy which was like 9 z-levels below my brook, eventually I blocked the hall and it made a nice pond, but the hall was forever lost.

[Krantz86]

carefully planned and totally controlled cave-in which wasn't as controlled as i expected.....

...doh!

[Blizzlord]

The fact that I haven't lost the game yet.
Jokes aside, I have never played enough of the game to have some Fun; or even to get enter the first cavern layer, yet I know most things you could know about it.

[Hammerstar]

Setting up an indoor moat from the nearby river. Forgot about pressure, and shut off the floodgate too late.

My drawbridge is now a giant floodgate.

[slothen]

watching an off-duty militia guy trip over a theif and get decapitated in one swing by the knife.  Once I locked the door to where the tame birds were to prevent egg collection.  A giant raven went wild, killed all the other birds, some exotic, killed two peasants, and then flew away.  For years my animal-catching attempts were thwarted by a group of thrips people that never left.  Once my legendary hammerdwarf militia commander, destroyer of sieges all by himself, went and dodged off a bridge because of a theif.  He fell 2 z-levels and landed right on his brain.  My prized ballistae battery fired a bolt that went sideways so far that it passed through fortifications 70 tiles away and killed a marksdwarf that was actually shooting at the same targets the ballista operator was supposed to be aiming at.  I once released an armed goblin that killed half the squad of trainees assigned to beat him up.  One time I was greatly embarrassed to be wearing tattered clothes.

[Ross Vernal]

Digging the input for my indoor waterfall at the bottom of the lake.

Watching a Kea steal an artifact wood ring.

Accidentally pulling THE LEVER instead of pulling the lever and melting the entire bottom half of my fort and 120 dorfs. @________@

[rtg593]

Trying to figure out why all my dorfs were being found dead. Finally, I located a very brief combat log identifying the culprit:

A named racoon.

[Loud Whispers]

I still refuse to accept the raven bomb disaster happened.

_{So many ravens...}

[Putnam]

I lost a fort made up entirely of SUPER SAIYANS to kobolds.

Probably has something to do with the fact that they all came riding on LFR's megalania, which are larger than elephants...

[Lordraymond]

So far dying to first level cavern creatures a total of four times, two due to troglodytes, one due to a crundle who sent dwarves dodging off a staircase to their death and one to a blind cave ogre.

Haven't lost to the cave ogre yet, I savescummed because I'm trying to get carts working and the autosave had triggered like five minutes prior, from now on I'm just walling off caverns instead of trying to build an impassable door.

[thegoatgod_pan]

Training militia in first ever fort.  I carefully moved a cage containing a lasher to the central barracks in the fort, checked on the forums for how to wire a cage to a lever, did so, released the lasher and watched it devastate my militia.  I panic draft everyone and toss them at the lasher.  He puts down everyone with minor broken bones and dances around them causing painful but not life threatening injuries (this was before combat aiming).  It took days before it was over

[Count Dorku]

Probably the time I decided to mass-designate multiple levels of my drop trap to be channelled out, leading to two miners falling and breaking their legs.

This was when I only had two miners, and a population in the low double figures. And no decent diagnoser.