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March 23, 2015 07:45 AM

His lifelong secret now out in the open, Bruce Jenner faces different reactions to his transition from his famous family. Subscribe now for instant access to all the details on the divided Kardashians and Jenners, only in PEOPLE.

Bruce Jenner‘s relationship with his ex-wife Kris’s best friend may have stirred up drama in the season premiere of Keeping Up with the Kardashians, but whether the pair ever had a real romance is still up in the air.

“Everyone assumed he was dating her,” a family insider tells PEOPLE of Bruce’s connection to Ronda Kamihira.

“Who knows how intimate things got, but they knew each other for a very long time.”

Which might explain why Jenner was so close with Kris’s former assistant just months before the Olympic gold medalist made headlines with the news that he is transitioning from male to female.

“It seems more like he confided in her,” says the insider. “She would buy him feminine things he wanted. They had some kind of special bond.”

And, despite pressure from Kim Kardashian to define his relationship with Kris’s longtime friend during the March 15 episode of E!’s reality show, Jenner denied that he was dating Kamihira.

“I don’t need to explain my relationship to anybody,” he said. “Nothing is going on. Certainly my intentions are not to hurt Kris. I don’t want anybody upset, but Kris is not going to tell me who I can and cannot hang out with.”

While Jenner continues to lie low amid the media frenzy, the famed decathlete is focusing on his quiet life outside of the spotlight for now, telling KUWTK cameras, “Living by myself out in Malibu has been really good. I kind of have my freedom.”

Reporting by JENNIFER GARCIA

For much more on how Bruce Jenner’s family is handling his transgender journey, pick up this week’s issue of PEOPLE, on newsstands now

Behind PEOPLE’s Cover: Bruce Jenner’s Family Divided

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