Lane’s Date with Todd

LANE: So anyhow, I was wondering if you could talk to Dean about maybe talking to Todd about me.
RORY: I guess.
LANE: And then maybe you could ask Dean to ask him out – for me.

It’s something of a puzzle why Lane doesn’t already know Todd well enough to ask him out herself since they have been attending the same small town high school for two years together. It’s possible that Todd is a relatively new student, starting the same year as Dean, in September 2000. Even so, she’s still had several months to talk to him a few times and decide whether she really likes him, or is just attracted to him. We must assume that Lane’s social skills with the opposite sex are very poor, as the incident with Rich Bloomenfeld demonstrated.