1. Point to the drink glass in front of you
2. Ask friend if they think the circumference or height of the glass is larger
3. Friend will invariably think that height is larger
4. Wager for a drink that that's not the case
5. Use a straw to measure the circumference and then height
6. Enjoy your free drink
Unless you've picked an a Champaigne flute you'll always win. To make it even more fun, for (4) wager that the circumference will be two times the height to make it sound more incredulous. For typical glasses you may go up to three!
I learned this trick from Things to Make and Do in the Fourth Dimension (https://www.amazon.com/Things-Make-Fourth-Dimension-Mathemat...), overall good book.