Ashlee Simpson, Boyfriend Evan Ross and His Mom Diana Ross Attend CrazySexyCool: The TLC Story Film Premiere in NYC Together: Picture

Rhonda Ross Kendrick, Diana Ross, Evan Ross and Ashlee Simpson
Ashlee Simpson stepped out with both her boyfriend Evan Ross and his mom Diana Ross at the CrazySexyCool: The TLC Story film premiere in NYC on Tuesday, Oct. 15; Evan says his famous mom "loves" Ashlee Johns PKI/Splash News

Diana approves! Ashlee Simpson stepped out with her boyfriend Evan Ross and his mom — the legendary Diana Ross — for his CrazySexyCool: The TLC Story premiere at the AMC Loews Lincoln Square in NYC on Tuesday, Oct. 15. And as Ross exclaims, his famous mom definitely approves of his new romance. 

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"She loves her!" the 25-year-old actor told Us Weekly on the red carpet at the star-studded event. "She's here," he added of Simpson. "She's with my mom sitting down. I had them take her to a seat." The two women were there to support Ross for his role as Dallas Austin in the film.

During the premiere, Evan was spotted sitting in between the former Supremes frontwoman, 69, and Simpson, 29. "Diana kept talking over and around Evan to Ashlee laughing and chatting and they seemed very close," an eyewitness revealed to Us. "Diana and Ashlee seemed to get along so well and Evan and Ashlee held hands while they spoke to Diana before the movie started." The trio also sat next to TLC's T-Boz and her family.

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Rumors first started in early July that Simpson and the "Upside Down" singer's son were an item when they were photographed leaving Teddy's nightclub at the Roosevelt Hotel together. One month later, the couple made their official debut when Ross came to support Simpson at the launch of the Jessica Simpson Fall Campaign 2013 at downtown hotspot Above Allen. The blonde beauty was there to host the event for her big sister's new line.

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The couple of five months were first friends before it turned serious. "It helps that they were friends first. They have a long bond," an insider explained to Us. "They already know each other really well."

Simpson last dated Boardwalk Empire actor Vincent Piazza for a year and a half before calling it quits in November 2012. The "Pieces of Me" singer has a son Bronx, 4, with ex-husband Pete Wentz. Simpson filed for divorce from the Fallout Boy rocker in February 2011 after three years of marriage.

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