Ashlee Simpson has been spotted out holding hands with the son of a music icon.  The “Pieces of Me” singer went out with Evan Ross, son of legendary singer Diana Ross, on not just one, but two occasions in less than 24 hours.

Simpson, 28 and Ross, 24 first hung out Monday night at the Roosevelt Hotel, staying until 1:30 a.m. At the end of their night, Ross led way out of the hotel’s club Teddy’s, guiding her with his right hand, while casually enjoying a smoke in his left.