Sheldon may have more neuroses than anyone on the planet, but some how this nerd has no problem doing one of the most awkward things... lending a friend money.
Leonard uses the board to attempt to find the perfect combination of movie theater and restaurant based on start times and Sheldon's idiotic requirements.

The Big Bang Theory Season 2 Episode 14 Quotes

Penny: No, I can't. Sheldon, honey, I don't want things to be weird between us.
Sheldon: Won't it also be 'weird' if I have to say hello to you every morning on my way to work and you're living in a refrigerator box and washing your hair with rainwater?

Penny: Wow, you've got a lot of money in there.
Sheldon: That's why it's guarded by snakes.