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So today I had flowers delivered to my friend's place of employment with a card reading "congratulations on the baby boy". The reason this is so funny is because his beer gut. I cant quit laughing, wish I could see their faces.
A guy in my office two cubes down turned 32. I sent an email to the office on his birthday saying "Everyone make sure to stop by Tim's cube for cupcakes! And wish him a happy 40th birthday!" He looked just old enough that 40 seemed a realistic number.
The rest of the day was filled with him yelling "No! I'm not 40!"
As senior pranks in HS:
- Snuck in over night and removed all of the chairs from the lunch rooms.
- Dug out "08" into the large hill outside the school everyone saw as you drove by, it stayed there for over a year.
... Earned ourselves 8 hours community service but a chuckle privately from the AP.
We would sift sand all the way to the dust stage in our chemistry lab. We would then pour the dust into the top on top of the heating/fins of the blower with it turned off. The next class would come and and turn the blower on and instant dust storm. We came back to class then next day and you could write your name on the chemistry tables. It took the chemistry teacher a few weeks to figure it was us and he didn't name names, but everyone knew we were guilty as hell.
A friend in high school drove a little geo metro. He was gone on a school function for a weekend so his car was parked at our high school. We jacked his car up, set it on some kind of "dolly", rolled it between two trees where it literally had about an inch between each bumper and the trees, and set it down there.

We did something similar in our HS. Except we didn't have the trees. We just turned the car 90 degrees in the parking spot with cars on either side.
My dad had a story where they let out some farm animals in the school (thinking like 6 goats or something manageable). They put a tag or marker on them (1, 2, 3, etc.) but left out one of the numbers so one was thought to be still loose somewhere for a good amount of time.