Drew is the definitely the hottie of the Liz and Drew coupledom, and as far as he's concerned, people randomly telling him how good-looking he is and a cop ripping up a parking ticket is just part of his day.
It's the bubble, Jack explains to Liz, a place where beautiful people enjoy a life of free drinks, kindness and outdoor sex.
Liz wonders how Drew can still be such a nice guy with all that, and Jack offers himself up as an example of someone who turned out okay after spending so much time in the bubble.
One giant Liz eye-roll later, Jack shows her a picture of himself at 25.
Suddenly Liz is seeing her boss in a new light, and decides that the bubble might not be such a bad thing.
Except, she soon learns, that the bubble tends to shut out all the negatives from the pretty person's life. He has no idea, for instance, that he's the worst tennis player ever, that there's no such thing as salmon bourguignon and the remedy for choking doesn't involve shaking a foreign object out or pushing it down with a fireplace match.
Liz decides to pop Drew's bubble, figuring a good guy like that deserves to have the truth told to him. It's a funny sequence of events that brings him back down to earth.
In the end, they're just two star-crossed lovers from different worlds, and Liz decides to end things. On the bright side, her chances of being hurt on the motorcycle Drew has no ability to drive have just gone way down.
The night's other story was about the relationship between Tracy and Ken.
After Jack notes during contract talks that Tracy doesn't need any more money, it dawns on Tracy that he doesn't need any more money. He quits.
Jack has one card to play, though: Kenneth's devotion to getting Tracy whatever he wants, whenever he wants it.
He's been doing this even after Tracy walks. Jack gets Kenneth to play along just enough to convince Tracy to come back, and order is restored.