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George Clooney, Stacy Keibler

Alequin/Bosch/INFphoto.com

George Clooney has solid a reputation for being a generous star; on Monday night, the Academy Award winner's kindness was caught on camera.

The handsome hunk and girlfriend Stacy Keibler stepped out for a bite to eat in NYC with celebrity pals Karen Duffy (one of Clooney's exes from the '90s) and Bill Murray. Clooney and Keibler changed out of their matching outfits for dinner after arriving in the city earlier that day.

After the star-studded meal at Il Mulino in the West Village, Clooney spotted a homeless man wearing a military jacket, military dog tags and seated next to a camouflage backpack outside the restaurant. The Descendants star proceeded to give the man some money and stopped to interact with him for a moment on the street.

Stacy is pictured standing next to Clooney, holding George's hand and smiling as she admires her boyfriend's charitable heart.

Although break-up rumors have followed the couple as of late, Keibler couldn't have looked happier with her BF's kind gesture.