The original post was getting long, but I wanted to include some other thoughts.
Originally my idea was for my girlfriend to eat something at all six restaurants AND do the chugging, but she said I was insane. Returning to a restaurant multiple times also means potentially having to explain why you were back for a second or third (or fourth) meal. For someone brave enough to commit to six menu items, go for it.
We crunched some numbers, and if we did the math correctly, there’s a 98.5% chance there will be a repeat roll and a 1.5% chance of rolling all six restaurants. There’s a 23.1% chance of rolling five restaurants with one repeat. There’s a 31.5% chance at least one restaurant will be rolled three times. There’s around a 5% chance that a restaurant will be rolled four or more times.
We haven’t really considered what to do if a restaurant is rolled four or more times. Maybe that’s when you return to the restaurant and live with the embarrassment. By the time you’re rolling a restaurant a fifth or sixth time, you’re (likely) rolling a restaurant you’re currently at anyway, so you can just order another item.