Need advice for picking UChicago essay topic?

Right now i’m stuck between two prompts. With the first one, I could write more about my personality, but the topic would overlap a little bit with my common app essay but it still wouldnt repeat anything i already said. However, I wouldn’t really be taking a risk with my writing/showing my quirky side, which I think they would want to see in their students. The second prompt asks for a short story, which I have a pretty good idea for. I would also be more quirky with my language/take a bigger risk in the second prompt which i know UChicago would like, but at the same time it would only be a fictional story where i dont even talk about myself or get to show other parts of my personality.
Would it be better to do the first prompt where I would talk about a topic slightly similar to my common app and not take a risk with my writing, or do the second prompt which would be a more interesting fictional story but not really show any details about me?

Everything you write reveals a bit about yourself–including the way you approach a short story.

My advice to you would be to write both essays, and submit the one that you feel speaks to you. I was in a similar situation, and having the ideas for both on paper really helped me choose.

It hard to tell when a quirky essay falls flat so definitely get a few people to read it. I’m not thrilled with the topic of my sons first go at it but I haven’t read it yet. He’s going to get his Eng teacher from last year who is in her 20’s to read it before me since she’s more hip to the quirky. The essay can make you at Uchicago though so worth investing time in. My son has a friend who got in based on a really amazing essay about a silly home improvement project and he didn’t get into any of the lower statistics but stuffier schools he applied to.