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.
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?