The sun rises on Day Nineteen. Kathryn and Steven slept in the tiny Smart car. Steven gets out, claiming that he's "stiff as a board." Can you imagine biking and running all that way and then sleeping all scrunched up? I would probably want to amputate my legs. They enter the dining room where the others are eating breakfast. Kathryn says she only slept for half an hour.

The team drives to Santa Maria and the castle of San Marco. Jim comes out wearing his fake buckteeth, and Anderson chuckles slightly. What a cool customer that Anderson is. This is the site of their next test. Anderson voice-overs that while the players have been cut off from family and friends, the producers have been in touch and gotten some information to use in this next test. Anderson explains to the players that a friend or family member of each one of them made a statement about them. They have to match the statement to the player. Each correct answer adds $5,000 to the pot.

The first statement is "The most redeeming quality about you is your ability to always offer a hug." Steven claims that one, and everyone agrees. The next statement is that the one thing that annoys this person the most about the player in question is the nagging. Jennifer says that it can't be her, because she's not married. Charlie says if they're limiting it to married people, it only leaves him and Kate since Steven is already eliminated. Kate allows that one of her kids could have said it. The next statement is that the thing they have least in common is fashion sense. Everyone looks at Jim. Jennifer says it couldn't possibly be her. This would be hard, mostly because you don't know whom they talked to. I know that my boyfriend would say very different things about me than my mother, for example. Jim agrees to claim that statement.