How would you solve this lunch break problem with people after a few failed attempts?

I tried this in Toronto with a friend and we both noticed the same thing: the social part mattered more than the perfect plan.

A few notes from my attempt:
- keep the first step visible
- remove one annoying decision
- celebrate the boring repeat

I had a disappointing first try a surprisingly good second try, and then a third attempt that taught me humility. So, naturally, I now have opinions