Ask Dr. Smartypants

In Ask Dr. Smartypants, players take on the role of an advice columnist providing “help” to a bunch of hapless questioners.

What You Need

  • A few full-sized sheets of paper.
  • Many sheets of note-paper.
  • One pencil per player.
  • A four-minute timer.


Give each player one sheet of blank white paper, roughly 5 1/2″ x 8 1/2″ in size. (In other words, cut some 8 1/2″ x 11″ pieces of paper in half.) Draw a picture on the top half of your sheet, and then pass it to the player on your left. When you receive a picture from the player on your right, examine it, and then write an advice-column-style question below it. It’s probably best if your question begins with “Dear Dr. Smartypants”, and ends with some kind of signature. When everyone’s done, shuffle all of the sheets into a face-down pile. Give each player a healthy supply of blank note-paper.

Generating the Prompt

At the beginning of each round, the current Judge selects one of the sheets of paper at random, shows everyone the picture, and then reads the letter aloud.

Writing the Entries

You now have four minutes to write as many responses as you’d like, in the voice of Dr. Smartypants. Write each entry on a separate piece of paper. When the timer runs out, you’re allowed to finish the entry you’re working on, but you’re not allowed to start another one. Shuffle everyone’s entries into a face-down pile.

Judging the Entries

The Judge selects one player to read all the entries aloud. After hearing them all, the Judge picks two favorites, and the respective creators receive one point each. If the same player created both of the chosen entries, that player gets both points. Use the two winning entries to track the points. After each player has been the Judge once, the game ends, and the player with the most points wins.


  • Game Design—Kory Heath
  • Playtesting—Jacob Davenport, Rich Potter, Chris Welsh, Liam Bryan