Pepper knows right off the bat that Jack would make a horrible assistant to Tony. They'd never get anything done. Still, she wasn't against keeping Jack close, and having him as an employee of Stark Industries did just that. Still, Tony had opened a can of worms and she would rise to the bait. "And here I thought you and Natalie got along."

There's a subtle smirk. Once, not too long ago, Pepper had been extremely jealous of the attention that Tony had paid to Natalie, but now that was water under the bridge and something she was able to joke about. "Or is that only when you're dying and not telling me?" Yes Tony, she's still sore about that whole thing.