It was a sad weekend at the Playboy mansion -- Mary O'Conner passed away on Sunday.
Hugh Hefner announced the unfortunate news via twitter writing, "Mary passed away today. We loved her more than words can say."
The former Playboy secretary worked with Hef for nearly 40 years, and made her small screen debut on "The Girls Next Door" alongside his then-girlfriends, Kendra Wilkinson, Holly Madison and Bridget Marquardt.
The ladies also took to twitter to share their sentiments.
"RIP Mary O'Connor. She was an amazing person who helped me through so much. But I know she's happy with her boo Captain Bob. :)," Kendra posted.
Bridget also tweeted, "Mary O'Connor will be missed. #RIPMary," and Holly posted, "Rest in Peace Mary."
Aside from acting as the 86-year-old's friend and confidant, Hefner also credited his former secretary with reuniting him and his now-wife, Crystal Harris after the two infamously called off their engagement in 2012.
Cyrstal shared her sadness on Sunday writing, "Hef's long time secretary & my dear friend Mary O'Connor has passed away. It's a very sad day here at the Playboy Mansion. We love you Mary."