Question: When Doug is telling jokes at the dinner, he asks the audience if they all received a number-two pencil. Then he tells a red-haired woman that he is just kidding. Would someone explain this joke?
Answer: It's nothing more than him saying her red hair looks like the red eraser on top of a pencil. He's asking did every table get a redhead.
Pencil erasers are more pink. Is it a common joke for people to think that redheads look like pencil erasers?
There are some pinkish erasers, but a lot also have very red erasers. I don't know if it was common per se, but certainly something someone would come up with off the top of their head in that situation. Plus, he puts his hand on her shoulder to indicate he's talking about her and not just talking to the room.
Question: I don't understand the last scene, in which the man from the paintball place is shown going home, and his wife complains about him buying frozen yogurt. Can someone explain?
Answer: A number-two pencil has long been standard for filling in the little boxes or circles on various paper evaluation forms, tests, and ballots. Doug didn't think he was funny enough to tell jokes at the roast and seems to be implying that his performance will be rated on a scale. For example, the audience would fill in a box somewhere between five for "excellent" to a one for "poor." He quickly clarifies he is kidding.
raywest ★
Also, as for the "Red" part: it's somewhat common for a red-haired person to jokingly be called that, just as a blonde person might be called "Blondie." I don't think her hair color was part of the joke; he just wanted to stop her from seriously looking for a pencil.