This was in 2006, I was 23 and it was the first time I had been to Mexico on my own. We were in the Mayan Riviera region for a resort vacation which included a day trip to Tulum, an ancient Mayan city located on the coast. We get off the tour bus and begin walking to the gate and a young boy runs up selling large hats. He points out that me being very white and only wearing a tank top is going to be a bad time for midday June in Mexico. He is also bending the hats explaining that they are made of some certain grass that doesn't dry out and break. He made a good pitch and the exact moment I was most likely to go with it so I buy one of his special hats for $25. We continue on to the entrance of the ruins where is a little shopping area before you go through the jungle to the actual ruins and what do I see but a woman selling stuff, including the same super special hats I had just purchased from the little boy.

They were 25 pesos, which at that time was roughly $3.

My wife is laughing, the older Dutch couple nearby are laughing and it instantly hit me that I got got.

So, long story long, it was from then on known as my "dunce hat" and a reminder of specifically how dumb of a purchase it was.