We will always, ALWAYS guess “box” or “circle” first. Knowing full well that the answer is never box. Or even circle.
Had a friend turn bright red trying to draw “elope”…because he thought it meant “to have a child out of wedlock.” Oops.
An attempt to draw “Charles Lindberg” once resulted in the guess “throw the baby in the washing machine”…I guess we got carried away?
Okay, I have three stories.
Number 1: Pictionary
I was playing pictionary with me and my best friend on one team, and my boyfriend and another good friend of ours on the other team.
The clue we got was Spain.
I drew a rudimentary map, and pointed at Spain. We got it.
My friend drew a circle with hair. And then an arrow pointing down.
When my boyfriend exploded: “How the hell is that Spain???” My friend (who is South American, has long hair, and is sometimes called Spanish) responds: “That was supposed to be ME!”
Number 2: Pictionary
Same game as above. The answer was pebble, and only my boyfriend and friend were doing it.
My friend is, again, drawing. He draws a stick figure with a huge ball on it’s back. He points a lot. My BF tells him to try a new track. He draws lots of little circles, and my boyfriend gets the answer.
When it was done, we asked him what the hell the first drawing was about. He replied: “Well, I’m was drawing Atlas, and was planning on working my way down from there.”
Number 3: Taboo
Me and my best friend (we are the best taboo team EVER) were playing against two really good friends of ours who are a couple.
Their word was ethics.
The guy starts: “Um… okay, if I guy kicked a puppy, what would he not have?”
Girl: “WHAT?? Who would kick a puppy??? What a horrible person! YOU’RE a horrible person! Why are you talking about puppy kicking?”
Guy: “Umm… okay… but what would he not have?”
Girl: “Puppy kicking is just WRONG…”
And so on. She just kept on yelling at him, and never even tried to get the clue. We all almost died laughing. 
Playing Pictionary with my family. My dad sucks at drawing. His word was “beehive.” He drew a big blobby circle-thing on the end of a wide stick that I assume was supposed to be a branch. The stick looked for all the world like a rifle. The circle-thing was not hanging from it, but stuck onto the muzzle end.
Me: Rifle?
Sister: Exploding rifle? Smoke gun?
Mom: Blunderbuss?
And so we continued trying to make sense of a rifle with a blob coming out of it until time ran out…
In a different game, I was drawing “beehive” myself. I drew, basically, this sort of shape, but a lot less detailed, of course. My friend guessed “stack of donuts.” I drew a woman with a beehive hairdo like Marge Simpson’s and pointed to the hairdo. Friend guessed “Marge Simpson - Homer Simpsons likes donuts! Forbidden donut!!”
You guys ever play Claymation? It’s like pictionary only with clay and you have to sculpt things. The first guess is almost always “worms!” or “ball!” It’s really fun. I suppose you could turn pictionary into claymation, just pick-up some Play-Do.
This reminds me of playing Canadian Version Trivial Pursuit with my family. My brother got a question who’s answer was “Graeme Green” - and he had no idea. My Dad tried to help him along by saying “It’s a kind of a cookie, and then the colour of the couch.”
After a few minutes of intense concentration, my brother anounces in a triumphant voice:
“Cracker Forest!”
Reykjavik comma Iceland fullstop.
Yeah, in my circle of friends, we call it “Sculptionary”. 
Fun stuff.
A few years back, my family was playing Trivial Pursuit. I asked my sister a question about a legendary figure of the Old West. She thought about it, then a smug look of enlightenment appeared on her face. “Eyett Werp!”
To this day, whenever we see a cowboy movie on TV, we say, “It’s Eyett Werp!”
My friends and I were playing Hummmmmble, a music game that’s like Trivial Pursuit. You roll the dice, land on a colored square, and pick a card. There are five different colored squares with different genres of music, and each card has five songs from each genre. Let’s say orange is “Children’s Songs.” If I land on orange, I pick the card and look at the song under the orange header–let’s say it’s “Camptown Races.” If I know the song, I hum it for my partner, who has to guess what it is. If I don’t know the song, I have to act it out.
Well, I had to either hum or act out “The theme from Dynasty” for my friend Julie once. I couldn’t remember how it went, and even if I did, she wouldn’t have recognized it. So I decided to act it out. This was one of the best charades I’ve ever done. First, I pulled my eyes up so I resembled someone “Asian.” Julie started yelling “Chickety-china the Chinese Chicken!” which cracked the other team up, but I kept going. I made my hands into a crown shape and put it on my head. Julie put Asian + crown together and yelled, “Oh MY GOD, DYNASTY!”
The other team didn’t even get us on the technicality that we didn’t say “Theme from,” they thought it was the best charade and answer sequence they’d ever seen.
We were playing Taboo at summer camp a few years ago, a bunch of 16-17 year olds, and my friend Garick was at the cards. He began: “I am a …”
immediately, his best friend blurted out the correct response:
“Virgin!”
One time I was playing taboo, and my word was “goldfish” I got them to say fish, and then said it was a kind of carp.
Big carp
small carp
male carp…
I decided to take another tack. I said "the name of this fish goes like this: ‘color’ fish.
red fish
blue fish
green fish
No! It’s an actual fish. It’s a precious metal. the color is a precious metal!
Silverfish
I gave up after that.
The game is actually called Claymania, sigh
Once when playing Taboo my husband had the word “chef” The clue he gave me was “I am…” I immediate rambled off messy, slow, lazy, irresponsable, grumpy, etc. I didn’t stop until I noticed everyone staring at me in shock, including my husband. Oops! :o
Also Claymation is actually a game too. It is loads of fun. You create clay creatures and fight them against each other. The rules can be found in a back issue of Dragon Magazine.
The phrase was “cold turkey”, so I drew a refrigerator and a fat bird with a big feathery tail. My aunt kept yelling out “Refrigerator Chicken! Refrigerator Chicken!” We still tease her about it every time the subject of Pictionary comes up.
My sister and I were playing a few years ago and the phrase ‘Uncle Wiggly’ came up. Struggling to get her to guess ‘Uncle’. I drew an ant and then crossed it out. Her guess was ‘Ant…no ant’. Next I attempted to get her to understand the gender change and the result was ‘penis…no penis’ . I think we lost that round but it’s still one our favorite phrases when we get together.
