Damon met Barroso while filming "Stuck On You" in 2003. He had gone out to a nightclub where Barroso was tending bar, and, after being recognized a bit too much, he hid behind the bar.
For fun, she put him to work making drinks. "[H]e made me a ton of money in tips that night, because of course everyone wanted to go and see him," Barroso recalled.
The two started flirting, and Damon asked her out that night, but she declined and said she had to go home and take care of her daughter. But the two did begin dating, eventually, and the rest is history.