To trust is to risk. When we lend someone money, we make ourselves vulnerable, hoping that the borrower will reward our trust and return the money at a later stage, possibly with interest or a reciprocal favor added. Generally, people are more willing to engage in a risky activity, such as buying a stock or starting a business, the greater the expected returns from the activity. This chapter examines whether willingness to trust follows the same logic, that is, whether it responds to changes in the expected value of trusting, much like willingness to take risk responds to changes in the expected value of risk taking in three countries of the Arab Middle East, namely, Jordan, Saudi Arabia and the United Arab Emirates and in the United States. The chapter shows that trust is promoted very differently in the Middle East than in the United States.