Writers Block and First Dates

During a 2015 interview Peter Mark Richman - author and actor who rocked the latter half of the twentieth century - was asked what he did for writer's block. His answer was to take two very different people, put them in a situation together, and let them talk. Take a rich girl and a poor man and put them together in a mechanic's shop for instance. His reasoning was that two very different people in a strange situation is going to create interesting interactions. 
A less formal and articulate version of that concept is trending around the internet today in the form of #BestFirstDateQuestions. The goal of this meme is to create a single question that gives the reader a (preferable amusing) description of the two participants of the date and the situation, all in one sentence, without referencing any of it. Two people, at odds, in a new situation, 
The wisdom of the elders is not reduced to amusing tweets.