The Dating Game is one a lot of people seem to be familiar with. Its one of many “game show” improv games, except instead of the audience asking the questions, like most of them, it is one of the improvisers asking them.
This is a hoop game that requires four to five people (depending on whether you want the MC of the game to be the ref or not). It’s a relatively low energy game, but when done well it can end up being hilarious. Most often, this relies on clever improvised answers rather than playing the game accurately. This game also requires more set up than most people would think. The improvisers need to remember certain rules that make watching it more entertaining. Here’s the way my troupe plays it.
You get four chairs, three for the contestants and one for the person asking questions. The contestants will each have a specific category of suggestion. Contestant One will be a real person. This means they will either be a historical figure or a celebrity. We tend to stay away from politics. Contestant Two is a fictional character. This can be somebody from a cartoon or somebody in a movie (specifically the character, not the actor), but really it just needs to be somebody that doesn’t really exist. Contestant Three is usually an inanimate object, but really this can be anything at all. Of course, you’ll have to get these suggestions while the Questioner isn’t there, as they’ll have to figure out the answers on their own.
You angle the fourth chair stage right and to one side, so the Questioner cannot see the contestants. Typically in this sort of setting you’d want a screen, but that’s a luxury most improvisers wouldn’t have. You don’t want them to be able to see each other because sometimes the way somebody sits can give away their identity. When on stage, you are that person/thing. You want to do more than “answer the question as George Washington would”.
Once everything is prepared, the MC gives a brief introduction, and the Questioner starts asking questions. For example, one can say “Contestant number one. Where would you take me on your ideal date?” The contestant would respond, and you would move on. You can give more than one contestant the same question, but don’t ever give all three the same question. That’s boring. Another thing you want to stay away from is asking them questions in order of one, two, three, one, etc. You can do this initially, but it feels rigid.
the Questioner will probably ask between six and nine different questions, depending on how long it takes to ask and answer them. Each contestant should try to provide funny/witty responses to these questions, but the improviser should prioritizing answering in a timely manner over giving the perfect answer. They should also expect to answer three or four questions. It’ll be harder to come up with questions than you think, but remember you can be silly here. My troupe likes the question “If you were ice cream/a cupcake, what flavor would you be?” but similar prompts get stale after a time. Remember, it’s the Questioner’s job to figure out who these three people are, so you want to ask them questions that will actually give you useful information, like “What are you usually doing around six in the afternoon?” (As a side note, Contestant Three is going to have a hard time giving real answers to many questions, especially if they’re a lawn chair or something. The easiest remedy for this is sticking with answering with lots of puns.)
After each contestant has answered a fair number of questions, the MC should stop the game ans say something along the lines of “Which contestants are you not going on a date with?” The Questioner should respond with, “Well, I won’t pick George Washington because I can’t forgive him for chopping down a cherry tree.” After saying something similar for another contestant, the MC should say “So why did you pick Contestant Three?” to which the Questioner will say “I’m really looking for somebody to relax with, so I think a lawn chair is the ideal choice!”
If the Questioner can’t figure out who one (or more) of the contestants are, the MC (and maybe the audience or even the contestant themselves) can give hints.