|He feels your pain.|
Didn't any of these contestants practice these at a dinner party first? Didn't any of the blank stares or slow responses of "Okaaaay ....?" tip them off?
Since these hanging, Asperger's-esque stories are a hallmark of the show, I'm guessing that everyone has been given strict instruction to tell very specific, but dreadfully dull things about themselves. They've maybe even been promised bonus points if they put on a look that says, "Oh, you're gonna love this one!". It's like the Jeopardy producer in charge of this segment is on a mission to maintain America's perception of nerds.
You know what would make a good trendy-thing-for-a-day Tumblr blog? One that transcribes every dull and random Jeopardy story. Like this (from Thursday's show):
If you're bored, tell me your own crappy Jeopardy story. Let's share our mediocre moments!