and Tony Romo had a low-key (but big-haired) night out on the town in West Hollywood on Monday.
The singer and the football star, accompanied by four other friends, hit the Key Club for the hard-rocking Metal Skool Night. The pair were seated in the VIP section, protected by a bodyguard.
But they were sweetly affectionate, according to an observer, who said Romo wrapped his arm around Simpson and rested his head on her shoulder. She, in turn, playfully rubbed her forehead on his cheek. (Awwww.) At one point, the pair also hopped onstage to rock out with the band.