Ashlee Simpson and Diana Ross: Surprising New Besties

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Ashlee Simpson and boyfriend Evan Ross with his half-sister Rhonda and Diana. (Johns PKI/Splash News)

Ashlee Simpson needn't worry about impressing her boyfriend's mom, who happens to be legendary singer Diana Ross, because she's already won her over.

Simpson, 29, and Diana spent Tuesday night supporting 25-year-old son Evan Ross at the premiere of his latest movie, VH1's "CrazySexyCool: The TLC Story," in NYC.

When Us Weekly asked the former "90210" star about how his two best girls get along, he gushed that his mom is a fan of Simpson.

"She loves her!" he exclaimed on the red carpet.

A source told the magazine that inside the theater, Diana and Ashlee's affection for each other was evident.

"Diana kept talking over and around Evan to Ashlee, laughing and chatting, and they seemed very close," said the insider. "Diana and Ashlee seemed to get along so well, and Evan and Ashlee held hands while they spoke to Diana before the movie started."

Ashlee was spotted with the Rosses at another big family event when Diana, 69, performed at the Hollywood Bowl in August. The blond pop songstress was seen at the afterparty.

Evan and Ashlee reportedly have been friends for years. However, they became a couple over the summer, and only made their first joint appearance at a Jessica Simpson Collection event in late July.

The actor is Ashlee's second serious boyfriend since her 2011 split from ex-husband Pete Wentz, father of her 4-year-old son Bronx. She dated "Boardwalk Empire's" Vincent Piazza for more than a year.

While it's great that Ashlee and the "Supreme Diva" hit it off, what we really want to know is how will Diana and Jessica get along?

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