The Saturday before Halloween, the night we had planned to go out and paint the town red in costume, Dan still didn't have one. He had put absolutely zero thought into it.
However, when we were at Target looking for parts of my costume, Dan came across a Waldo Halloween costume. It was just a stripped shirt with a graphic of glasses hanging from a fake pocket. Merely $10. He got so excited by the idea of being Waldo. We went straight to the women's hat section and found him one with a poof on top and he went home and painted stripes on it.
So, that night, we went down to 4th Ave, which can best be described as the restaurant and bar row favored by hippies and recent college graduates. Do you know what is a big hit with drunk people? Finding Waldo. So many people shouted "I found Waldo!" while we walked from restaurant to restaurant. We were even eating dessert, seated by the window, and people were taking pictures with Dan in the background through the glass.
The most fun night was Halloween, though. I had the idea that Dan needed to photobomb all the pictures of the teams at trivia that night. He coordinated with the Quizmaster and the two of them had so much fun sliding Dan into the background of all the pictures. He even Waldoed another Waldo.