Dating couple Jason and Melanie from Cleveland, Ohio, are ready to get married and settle down, but first they want to hit the open road and travel across the country. 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.

A married couple struggling with debt could win cash if they participate in controversial tasks involving unsuspecting loved ones.

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.

New parents Callie and Daniel from Sanger, Texas, moved into their dream home and would love to build a beautiful outdoor living space for their family to enjoy. 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.

High school sweethearts from Ohio who want to lower their debt and provide for their children could win cash if they complete scandalous tasks involving unsuspecting friends and relatives.

A married couple with a baby on the way receive a chance to win cash -- if they can complete scandalous tasks involving unsuspecting friends and relatives.

Soon to be married couple Jessica and Rod from Seattle, Washington, have a dream of returning to their home state of Texas to be closer to family.