Engaged couple Mike and Sylvia from Palatine, Illinois, are eager to get married and start looking for a house. Host and legal analyst Matthew J. O'Connor presents the couple with two scandalous and controversial tasks involving their unsuspecting friends and families for various cash prizes. The couple must then decide how far they are willing to go to make their dreams a reality.

Married couple Desirae and Sean from Illinois, are eager would love to start a family and would like to see a fertility specialist to make their dreams of being parents come true. Host and legal analyst Matthew J. O'Connor presents the couple with two scandalous and controversial tasks involving their unsuspecting co-workers and families for various cash prizes. The couple must then decide how far they are willing to go to make their dreams a reality.