What's that supposed to mean?

Oh you don't know about jail? Oh you would love jail.

Why would I love jail?

Because... You would love it.

I don't think our company actually needs any more insurance. So I am out.

Character
Roy
Roy
Dwight
Dwight
Oscar
Oscar
Phyllis
Phyllis
Pam
Pam
Episode
WUPHF.com
The Merger
Mafia
Here Comes Treble
Sexual Harassment
Season
5
2
4
6
1