I would choose to play a grandmaster but lose, that way you can at least learn something.
Would you rather

nah give me a beginner any day.
Playing a GM would be... a very predictable loss, and I think generally uninstructive without a lot of discussion.

Would you rather gain 100 rating points but lose the tournament or gain 10 rating points but win the tournament?
Would you rather play a game of chess or kill yourself?
I would kill myself because chess is the worst "sport"

Or play chess sitting in sh*t that smells like chocolate pudding.

WOULD YOU RATHER METAPHOR-(if "limbo"/"purgatory"/"hell" were 100℅ real and you were to go there)...
Would You Rather spend your never-ending eternity playing chess completely alone & moving both sides of the board so to win/lose against yourself OR spend your endless eternity playing chess with a total stranger who had zero knowledge of the game along with a flat out contempt for the game's entire concept?
Here you can make up would you rather questions and have fun! I will start.
Would you rather play against a beginner and win or play against a grandmaster but lose?