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After briefly dating Hefner, she quickly transitioned to his “social secretary” and moved into an apartment at the first Playboy mansion, located on State Street in Chicago’s exclusive Gold Coast section.

Arnstein oversaw the risqué activities at the mansion whenever Hefner was away and ran his day-to-day meeting and appointment schedule in the years before he moved out to California full time.

After talking about her chances of performing at the next Super Bowl and her Las Vegas residency, we finally got to the juicy part: Drake. Lo and Drizzy have rumored to be a fling since sharing a moment together on Instagram back in December. “Actually, he sent me a song that he wanted me to be on. At that same prom night, you could hear new vocals from the duo off their unreleased record.

They’ve been spending significant time in Los Angeles and Las Vegas the past few months, and paired up at a Winter Wonderland Prom in Hollywood.

When she reached her 30s, Arnstein began dating younger men and fell into a romance with a 22-year old drug dealer named Ron Scharf.