Lorelai has been through a lot of relationship angst lately, and the show now gives her a bit of comic relief in this area when Kirk asks her for a date while delivering a package to the inn. We know that Kirk is very lonely, and has been actively seeking a girlfriend at least since Sookie’s wedding (he is delivering her wedding photos, as a little reminder). It’s a chance for Lorelai and Rory to later joke about Kirk being Rory’s stepfather – this is the second time Rory jokes about Lorelai marrying Kirk.
However, despite plenty of humour at the expense of Kirk’s awkwardness, the situation is handled quite sensitively. Lorelai turns him down kindly, saying that she’s not ready to date anyone at the moment, and would prefer to keep Kirk as a friend. Kirk on his part takes the rejection gracefully, and without resentment. He tells Lorelai that she is the prettiest girl he has ever seen, except for models in pornographic magazines – and although this is a weird compliment from a rather strange person, I think at this point, Lorelai is quite flattered to receive it. She does seem willing to accept compliments from strange quarters when her ego has taken a bruising.
When Lorelai refers to Kirk as her friend, this seems to be the first time she has openly acknowledged him as such, and is a bit of a turning point in their relationship. From now on, Kirk feels less like the town weirdo, and more like Lorelai’s eccentric friend.
The Annotated Gilmore Girls 