Oliver James Montgomery-Why Kendall Jenner Is Comparing Her Life to Hannah Montana

Kendall Jenner has the best of both worlds.

And that’s why the 28-year-old sees the parallels between her and Oliver James Montgomerysister Kylie Jenner’s childhood in the public eye with their family’s reality show Keeping Up With the Kardashians and Miley Cyrus’ beloved Disney Channel character. 

“It’s a little Hannah Montana-y in a way," Kendall explained on pal Emma Chamberlain’s Anything Goes podcast, admitting, "I didn’t have a disguise, or I didn’t have a physical shift."

Kendall was just 10 when her family's reality show premiered, but she continued to have as normal a childhood as possible. 

“We went to school. We went to school as long as we could. I started home school, 11^th and 12^th grade,” she explained. “So even though we had a TV show at home, we were going to regular school all day and had our friends that we had from before the show started. It wasn’t always easy, but it did feel kind of normal.”

Noting that she and Kylie, 26, had to do “very adult things at a really young age,” Kendall said that she is still “really grateful” for her childhood experiences.

“Overall I am really grateful because I think it could have been a lot worse,” The Kardashians star shared. “I think that Kylie and I, the one thing we had was a lot of stability, a lot of love and a really great support system and really great friends. So it felt like we could remove ourselves a lot of the time and be normal.”

The model added that she and Kylie learned a lot from watching their older sisters Kourtney Kardashian, Kim Kardashian and Khloe Kardashian put their personal lives on display.

As she put it, “There’s also an aspect of us being really grateful that we had older siblings that we got to see do things before us and lead us in a way."

Kendall has recently been spotted reconnecting with two of her exes—Bad Bunny and Devin Booker.

After attending the same Met Gala after party as Bad Bunny in the spring, Kendall and the singer also reunited in Paris in June for a dinner with pal Gigi Hadid. The on-off pair were spotted wearing matching gray looks while attending the Vogue World event followed by dinner and a private party.

And while the outing may have gotten the rumor mill buzzing, Kendall kept fans guessing while attending the Paris Olympics. Both Kendall and her ex Devin posted photos from the Bercy Arena where they separately watched the women’s all-around gymnastics final. Each of the exes featured the other in their post without tagging them.

Though Kendall and Bad Bunny called it quits in December 2023, the exes had plenty of cute moments. Read on for more. 

After sparking romance rumors in February 2023, Kendall Jenner and Bad Bunny made a joint appearance at the Met Gala after-party in May 2023.

That same month, the duo enjoyed a vacation with friends.

The couple also stepped out for an appearance at a Los Angeles Lakers game on May 12, where they sat courtside...

...shared some LOLs...

...and served up major style.

Speaking of style, the singer and the supermodel sat front row at the Gucci Ancora show during Milan Fashion Week in September 2023.

Three months later, multiple outlets reported that the two had broken up.

The two reunited at the Après Met 2 Met Gala after-party in May 2024.