Theo has never had a close relationship with his mother. As a teenager, he rebelled against her and eventually became emancipated and lived on his own. So it's no surprise that she doesn't know much about him.
Obviously, the clever people who think up the Road Rules missions found a way to work this into the show. The gang goes to Emory University and is told they will be participating in a game show. Upon entering the auditorium where the game show will be held, they meet their partners: their mothers (or in Msaada's case, her father). The object of the game is to answer as many questions as possible correctly about their partners. If the Road Rulers as a whole answer enough questions correctly, they get 4 $1,000 coins. Although they get embarrassed by some of the questions, they all do well enough to win the coins.
But there are still 6 more coins to be won. In order to win them, each Road Ruler and his/her parent must bungee jump from about 100 feet up. Each pair that successfully jumps gets a coin. Everyone convinces their parent to jump, although Theo has a harder time than the rest. But when his mother finally jumps, he feels that they have finally connected in a way and bridged the gap they created years ago.