Kendall Jenner Makes Rare Comment About Her Back-to-Back Relationships

Kendall Jenner explains why she took a break from dating after a series of serious relationships.

“I’m actually in a time like me right now,” Jenner, 30, said on the Friday, January 9, episode. Owen Thiele“In your dreams” podcast when asked about his dating situation. “I know this might sound cheesy… but when I turned 29, I had a crisis as I approached 30.”

She continued: “When I turned 29, I remember saying to myself: I feel like I’ve been in [relationships] and there is nothing wrong with that. I’ve had great relationships, I’ve had some not-so-great relationships, but I felt like until my 20s, I was into a lot of things. I was in a few consistent long term relationships… close together.

Jenner famously dated an NBA star Devin Booker on and off from 2021 to 2022. During one of her breaks with Booker, 29, Jenner was briefly linked to the singer Bad bunny in 2023. The couple broke up in December 2023 and Jenner remained single before finally reconcile with Booker again early 2025.

Related: Kendall Jenner and Devin Booker Relationship Timeline

Kendall Jenner has had many ups and downs in her relationship with Devin Booker. Jenner and Booker were first spotted on a double date — with other people — in May 2018. While the model was seeing Ben Simmons at the time, Booker was linked to Kylie Jenner’s then-best friend Jordyn Woods. THANKS! […]

“I never really had my 20s for me,” the model told Thiele, 29, on Friday’s episode. “When I turned 29, I made a minor commitment to myself. I was like, ‘I’m not going to reject anything.’ [and] I’m going to stay open to whatever works for me, but I really wanted to have a “me year” where I choose myself.

According to Jenner, her “year of me” was focused on prioritize self-care and inner happiness.

“That doesn’t mean people came into my life or didn’t come into my life, [but] “It wasn’t really about that,” she said. “It was just about saying, ‘I want to have fun, I want to choose myself and I want to do what I want to do.'”

The 818 Tequila founder further noted that she tends to be “a really good girlfriend.”

“I really love being there for my partner and I really put him first most of the time,” Jenner said. “So, I think, when I turned 29, I was like, ‘I really want to prioritize myself right now.’ So, that’s where I’m at.’

Jenner wanted to “fall in love again” with herself after her breakups with Bad Bunny and Booker, respectively.

“I felt like I had a little more relationship trauma throughout my 20s than I realized,” she said. “A lot of things were coming out [and] I was also experiencing my Saturn return. …I was in my Saturn Return and it felt like it was endless, and I was really, emotionally, just like, “What’s happening? There’s too much going on.

Jenner proclaimed that she was “definitely a lover” and that she still hoped to meet The One.

“I have a ton of dreams for myself, obviously there are personal ones, that is, a beautiful family and things like that,” she revealed.[I want to be] in a beautiful relationship with a lot of understanding and love and all those things.