Weird Things About Caitlyn Jenner's Love Life Post-Divorce From Kris

Caitlyn and Kris Jenner were Hollywood's power couple for 22 years before calling it quits. They brought together the ultimate modern-day Brady Bunch, with kids from their previous marriages. Caitlyn (then Bruce) had Burt and Casey with Chrystie Crownover and Brody and Brandon with Linda Thompson. Kris, of course, gave us Kardashian royalty — Kourtney, Kim, Khloe, and Rob — from her marriage to Robert Kardashian Sr. When they got together, they added Kylie and Kendall Jenner to the mix, making them the ultimate blended family. However, their marriage eventually ended, and Kris moved on with her current partner, Corey Gamble. As for Caitlyn, her love life has been quiet — at least for now.

The former couple met in 1990, around the time that Kris was divorcing Robert. Caitlyn recalled to The Times that they quickly fell in love and got married not even a year later. "We hit it off right at the beginning, and we were married after five and a half months," she said. "I was infatuated with her, because she was very different from me. But yes, I'd have to say, it was love at first sight." Fast forward to 2013, and they decided to part ways about two years before Caitlyn publicly came out as transgender.

Unlike Kris, who has found new love, Caitlyn's romantic endeavors seem to have taken a backseat. But don't count her out just yet — a relationship expert thinks that could change in the future.

Before anything else, it's important to understand that Caitlyn and Kris Jenner's separation wasn't primarily about Caitlyn's transition. "Twenty percent was gender and 80 percent was the way I was treated," Caitlyn said in an interview with Vanity Fair, noting that in the early days, Kris leaned on her to help keep the family afloat, but as Kris' career skyrocketed, the marriage hit turbulence. "I think in a lot of ways she became less tolerant of me. Then I'd get upset and the whole relationship kind of fizzled." Kris didn't disagree, mentioning that Caitlyn's internal struggles added tension. "He was married to me, and he wasn't who he wanted to be, so he was miserable." Caitlyn echoed this sentiment on Rob Lowe's "Literally!" podcast, admitting, "Because of my frustration with myself, I might have been a little bit shorter with her near the end," she said.

What's even more interesting is that Caitlyn and Kris didn't just call it quits in their prime — they were 64 and 58, respectively, when they split. But Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking, explained in an interview with Nicki Swift that these so-called "gray divorces" are becoming more common. "With Golden divorces on the rise, I think it's just become more acceptable. You see other people doing it, and gray divorce is a thing now. If others can, so can you," she said. "People are living longer and they want to spend their lives being happy. Or there is the empty nest syndrome, and you suddenly realize there is no connection anymore."

Although Caitlyn and Kris Jenner claim they parted on good terms, their relationship is now virtually nonexistent. Despite their initial vows to remain "best friends," that plan clearly didn't pan out. Caitlyn opened up about this on "This Morning," admitting that they rarely communicate directly — if at all.

"Well, Kris, I never really talk to anymore. Yeah, it's sad," she said. "If there's any communication, my manager kind of talks to her, and when you have as many kids as I have, you're closer to some than you are to others. ... I certainly see them, and we do this and that." She also hinted at her strained relationship with the rest of the Kardashians. "I'm much closer to the Jenner side, but Kris, I don't really have any more contact with her," she added. "It's kind of sad because we went through a lot."

The fallout likely stems from Caitlyn's revelations in her book, "The Secrets of My Life," where she claimed to have told Kris about being transgender early in their relationship. Kris didn't take kindly to the book, expressing her frustration during a "Keeping Up With the Kardashians" episode. "I read it, and basically, the only nice thing she had to say was that I was great socially at a party one time," she lamented. "None of it makes sense. Everything she says is all made up. Why does everything have to be that Kris is such a b***h and an a**hole?"

Since parting ways with Kris Jenner, Caitlyn Jenner hasn't exactly been making headlines with a new love interest. There was some buzz about her and Ronda Kamihira, one of Kris' close friends, but Caitlyn shut that down, clarifying they were just good pals. Apparently, Ronda was one of the few people Caitlyn felt comfortable sharing her gender identity struggles with. "Years ago I confided in Ronda, and she really has been a friend that has supported me," she dished in an "I Am Cait" episode, according to People. "I've really got a great support group. From that standpoint, I'm blessed."

As for romance, Caitlyn isn't exactly on the lookout. "To be honest with you, I don't see myself having a relationship with anybody in the future. It's not what I'm looking for," she admitted to OK! Magazine in 2020. "I've been married three times. I've been down that road ... I want to enjoy my life and I have great friends."

Matchmaker Susan Trombetti told Nicki Swift that Caitlyn might be steering clear of romance due to fear of rejection. "They have had years of practicing the fine art of building up walls, and do not let someone in as easy as when they were in their twenties," she said, but also suggested that love might sneak up on Caitlyn when she least expects it. "All of this said someone will come along for Caitlyn. ... Other older adults start losing their spouses and find themselves uncoupled and looking. It will be a surprise to Caitlyn, but she will find someone and be like a giddy teenager in love."

Despite not having a romantic partner, Caitlyn Jenner seems to be thriving in her singlehood. As matchmaker Susan Trombetti pointed out, Caitlyn has a solid support system of family and friends, making her life anything but lonely. "I don't know Caitlyn personally, but a few good friends who are compatible with her travel style and other pursuits could provide a good network and outlet along with family," Trombetti explained to Nicki Swift. It sure sounds like Caitlyn's doesn't need a plus-one to feel complete.

What's more, Caitlyn is also likely funneling her time and energy into things that she's passionate about instead of searching for a new romantic spark. "Volunteering for causes that interest you and being involved in your community can be very fulfilling. Caitlyn has a lot to give," added Trombetti. "Feeling valued and providing value to others can be very fulfilling and meaningful in life. It's purpose-driven. Caitlyn is giving every day. The example she sets from living her true self is helping others see it's always okay to be you."

Kris Jenner might have some lingering beef with Caitlyn Jenner, but Caitlyn still holds a soft spot for Kris. According to insiders, Caitlyn has some regrets regarding her handling of her transition, especially about keeping Kris in the dark initially. It upset her that Kris found out from E! executives, thanks to Caitlyn brokering a deal for "I Am Cait" before having a heart-to-heart with her ex.

"Caitlyn will always have love for Kris, and even after the divorce — which had nothing to do at all with transitioning — really has come to regret not talking with Kris personally first," the insider dished to Page Six. "It hurt [Caitlyn] to learn that Kris found out from network execs." Despite the rocky communication, Caitlyn tried to mend fences, at least in public perception. She participated in the "House of Kardashian" documentary to clear up any misconceptions about Kris. "Caitlyn not only partook in the documentary to defend her family, but to set the record straight that Kris really had no idea — other than what [Kris] discussed in Vanity Fair."

The silver lining is that Caitlyn maintains a strong bond with Kylie and Kendall Jenner, the daughters she shares with Kris. In an appearance on "The Skinny Confidential Him & Her" podcast, Caitlyn mentioned they stay in touch and enjoy quality time together. "[We] just have a glass of wine and talk about stuff and this and that. And so from that standpoint, we're a lot closer," she said. "Kendall's not that — she's always very kind of a little bit more secretive. We're still very close, but it's kind of harder to figure out where Kylie's more of an open book."