Jean Allen and her 8-year-old daughter Victoria joined Clooney on Tuesday night for the premiere of The Monuments Men.
Before the big night out, the 42-year-old mother was treated to a day of red carpet pampering. She got her hair done at Ted Gibson's salon and wore a gown from Rent the Runway.
She then sat down for what she thought was a one-on-one interview with "Good Morning America" anchor Lara Spencer about the experience, with the single mom admitting she hasn't been on a date since 2010.
Clooney surprised Allen during the interview and sat down to chat, giving her a heads up on what to expect on the red carpet.
"We are going to get out of the car," he explained. "There will be a lot of people taking pictures, and they will be yelling like crazy."
Jean got the date by entering a $10 "Win a Date with George Clooney" charity raffle on Omaze.com.
She shares Clooney's love for his Satellite Sentinel Project for Sudan, which helps monitor human rights abuse.
(ABC News contributed to this report)