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A red two player free roam icon will now appear on Denise's porch near the door.
The icon will appear there when she is home and will go on a date.
Note: If both enter a car, the passenger will have free aim with a machine gun.
Do not try to kill Denise, because you will never be able to date her again or play in two player mode at her house.
Additionally, once you get your girlfriend, take her on a date.