Kiernan Shipka Don't Trust

Isn't that just how time flies? One minute Sally Draper's serving as a pint-sized mixologist for the always-appropriate Don and contemplating mortality after the death of her grandfather, and the next she's playing herself opposite a semi-ironic James Van Der Beek in a sitcom.

"Mad Men" star Kiernan Shipka, who's proven her acting chops as the Drapers' oldest child and is growing into a beautiful young lady, will guest as herself in tomorrow's episode of "Don't Trust the B---- in Apartment 23." Here's a clip of her helping Van Der Beek prepare for a role.