Why Kendall Jenner’s Friends Aren’t Convinced Her Dating Bad Bunny Again Will Last Long Term
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Earlier this year, it was rumored that model Kendall Jenner and musical artist Bad Bunny were starting a romantic relationship; by October, they were being seen together less and less. Now, just before the holidays, it has been reported they may have split for good. Jenner split with her on-again-off-again ex-boyfriend Devin Booker in 2022, and was reportedly spending time enjoying the single life before meeting the Puerto Rican rapper.
Then Bad Bunny, or Benito Antonio Martínez Ocasio, swept her off her feet. Here's their relationship timeline and its potential end so far.
February 2023
The pair were first seen together out for a date in Beverly Hills. Jenner and Ocasio were spotted leaving Wally's, a popular eatery amongst the rich and famous. E! News said that Hailey and Justin Bieber were also at the restaurant, which could mean they were on a double date — or everyone wanted brunch at the same time.
March 2023
The new couple were out in West Hollywood in early March having dinner with friends. They shared a hug and possibly a kiss before parting. By he end of the month, the rapper seemed to be mentioning his new gal friend on Eladio Carrión's track “Coco Chanel.”
In the lyrics, he sings, “I’m not bad, baby that’s a gimmick / But the sun in Puerto Rico is hotter than in Phoenix / She knows it.”
Booker, Jenner's ex, plays for the Phoenix Suns. Elsewhere on the song, he shouts out “Scorpio women,” which is Jenner's birth sign. A source told US Weekly that month that Jenner wasn’t “really looking to date anybody.”
“Things are not official between Kendall and Bad Bunny, but they’re seeing each other on a regular basis and getting to know each other better,” the insider said, but Jenner's feelings were “starting to grow” after “spending more time” with him.
“It’s not super serious, but she likes him and is open to seeing where things go with him. Kendall appreciates how he treats her with respect and he makes her laugh,” the insider added. “He’s very charming and she thinks he’s a great guy. Although things are still fairly new, she definitely sees potential.”
In late March, they were seen out at dinner again and an eyewitness said they were “openly kissing” and “being very affectionate.”
April 2023
In April, TMZ reported the couple had gone horseback riding together, so things have definitely heated up. On April 15, Jenner watched Bad Bunny's performance at Coachella in Indio, California, and was captured dancing on the crowd on a TikTok. Later that weekend she was also photographed by his side as he whispered to her in the crowd.
They were then seen together at Tyler the Creator's concert in Los Angeles on Wednesday, April 26, dressed casually and laughing as they walked through the street.
On Saturday, April 29, they were seen in NYC heading to Carbone, a celebrity favorite. They later headed to Pergola for after-dinner drinks, leaving together in a blue Mercedes. For the night out, Jenner stunned in a sleeveless semi-sheer asymmetrical crop top that matched her dark brown miniskirt trimmed in tan fuzz. She completed the look with knee high leather boots covered in belt details.
The rapper wore black slacks with a black and yellow leather jacket and a pair of black sunglasses. He had one square-toed black boots and a gold chain around his neck.
May 2023
Jenner and Bunny didn't walk the Met Gala red carpet, but they attended an after-party together.
A source told People that same day that the couple was becoming “more serious.”
“They are very cute together. Kendall is happy,” the source said. “He is a fun guy. Very much a gentleman and charming. She likes his vibe. He is very chill.”
“It was a slow start, but they spend almost every day together now,” the source continued. “He hangs out with her friends and she hangs out with his. It's more of a relationship now. Kendall is not seeing anyone else. She really likes him.”
On May 11, E! reported that Bunny and Jenner went on vacation together with friends. A TikTok revealed this, with Bunny and Jenner appearing alongside each other in a video taken by photographer Renell Medrano and posted to his page. He ultimately took it down. A screenshot from the video of Bunny and Jenner remains online here.
Another source told UsWeekly that day, “Things are going really well for Kendall and Bad Bunny and she definitely sees long-term potential with him. She feels like he’s the complete package and he treats her like a total gentleman.”
They added that she is “really attracted” to the artist’s confidence.
“They are having a great time together, and she appreciates that he gets along with all of her friends,” the source said. “They complement each other on so many levels and she’s enjoying getting to know him better every day.”
On May 12, they were seen sitting court side at the Lakers playoff game in Los Angeles.
On May 24, a source gave more detail to Entertainment Tonight about how Jenner and Bunny's more serious relationship was progressing. “He is not only spending more time with Kendall, but with the rest of the family as well,” the source said.
There's “potential” for the pair's romance to be more “long term,” the source added. “They’re both always laughing and smiling together and have similar family values.” Jenner herself is “enjoying their low-key relationship and is excited about where they're headed.”
June 2023
On June 21, interviews with both Jenner and Bunny came out where they discussed their intention to keep their relationship private.
Bunny told Rolling Stone of keeping his personal life under the wraps, “I know something is going to come out. I know [people are] going to say something. People know everything about me, so what’s left for me to protect? My private life, my personal life.”
When asked if he wanted to clear up any rumors about his relationship with Jenner, he repeated that line: “That’s the only answer. In the end, the only thing I have is my privacy.”
Jenner told WSJ magazine, meanwhile, that she had “no comment” on Bunny.
“I try [to] find the balance of keeping things private and keeping things sacred, [and] also not letting the unfortunate frustration and stress of everyone trying to get in on it stop me from enjoying my side,” she explained. “Does that make sense? I’ll go out of my way to do things as privately as possible because I just think that that’s the healthier way of dealing with relationships anyway.”
July 2023
A source told People that Jenner and Bunny went on vacation together to Gozzer Ranch Golf & Lake Club in Harrison, Idaho.
The source described them as “really cute” and “so happy together,” adding, “They definitely seem in love, and super serious. They're really friendly. Kendall is so low key that plenty of guests don't even know who she was.”
Jenner and Bad Bunny were also seen back in West Hollywood on July 27, enjoying a dinner date together at Sushi Park. It's one of their favorite spots, and they were also seen there with friends in late June.
That same day, on an episode of The Kardashians, Jenner shared that her mom Kris has gifted custom dollhouses to all her siblings for Christmas and decorated her to manifest a marriage.
“She put an engagement ring in mine, because she thought it was manifesting an engagement for me,” she said in a confessional. “So if that tells you anything about where my mom wants me to be in life.”
August 2023
Videos and photos of Jenner and Bunny kissing and showing PDA came out when the couple attended Drake's Los Angeles concert together. The date night marked one of their most affectionate public outings yet since they started seeing each other.
Later in August, Bunny appeared to soft launch their relationship on his Instagram Stories. He shared a video featuring a woman he called “mami” whose voice resembled Jenner’s. He also wore a “K” initial necklace in one photo and had a photo of her 818 tequila line in another.
Kendall on Benito’s insta story 🥰 pic.twitter.com/21odRhMWnm
— kendall jenner outfits 💋 (@kenjenstyle) August 27, 2023
September 2023
Throughout the month, Jenner and Bunny had a string of public dates, including at the Met Opera in New York City and at Gucci’s fashion show in Milan.
Bunny also addressed why he is so against discussing his romance with Jenner in a Vanity Fair profile published in mid-September.
Regarding fans who disapprove of him dating Jenner, he said, “they don’t know how you feel, they don’t know how you live, they don’t know anything, and I really don’t want them to know. I’m not really interested in clarifying anything because I have no commitment to clarify anything to anyone. I am clear and my friend Jomar [Dávila] is clear and my mother is clear. They are the only ones to whom I have to clarify anything. As for Juliana Dominguez from Mississippi [a random fan name], I have nothing I need to clarify to her. Never. About anything.”
“There are people who say that artists have to put up with it,” he continued. “I don’t have to accept anything and everything because I wanted to be an artist. At the end of the day, you listen to me because you want to. I don’t force you to.”
He also revealed that he isn’t about to get engaged to anyone. When asked if he wanted traditional milestones like a wedding and kids, he said, “no, I don’t think so,” adding at least “not now.”
After shortly after their appearance at Gucci’s show, Jenner and Bunny appeared in the fashion house’s newest campaign together, released on September 30.
October 2023
Ahead of Bunny’s appearance on SNL on October 21, the artist appeared to subtly reference his romance with Jenner in his promo. Bunny squashes a mosquito, with the video being captioned “be careful.”
He made the same comment in a video he posted on his Instagram Story of him and Jenner on a hike in August. He told her, “mami, be careful” due to the mosquitos. That video was considered part of his soft launch of their relationship on his social media, as Jenner did not appear on camera in it, but her voice was heard.
The night of his appearance, Jenner was by his side for the SNL after party at L'Avenue.
A week later, Jenner and Bunny were photographed together getting brunch on October 29 at the Beverly Hills Hotel after Jenner’s Halloween party the night before. An eyewitness described them as “being cute and affectionate” to TMZ.
November 2023
On November 14, Jenner sparked some concern among fans on Instagram that she and Bunny may have be having issues in their relationship. Jenner posted an Instagram of a sunset with a caption that read, “what’s meant for me, will simply find me.” One commenter noted that the post seemed breakup-esque, but no reports came out signaling any trouble between Jenner and Bunny. Neither spoke about their status either.
Two days later, a source told Us Weekly that Jenner’s friends were not convinced she and Bunny would last. “Kendall’s friends don’t think she’ll be with Bad Bunny forever,” the source said. “Despite the breakup rumors, they are still seeing each other, but [Kendall’s pals] don’t see a huge spark between them or any long-term potential. If Kendall’s happy, then they’re happy for her, but they’ve seen her happier before in past relationships.”
December 2023
Jenner was still flying solo on Thursday, December 14, in Aspen, Colorado, when she attended the Revolve + FWRD Pop-Up Shop party. The tequila brand founder was wearing a black jacket and matching pants with black high heels. Her 818 Tequila was being served at the pop-up and she spent the night mingling with guests like Devon Windsor, Raissa Gerona, and Lais Ribeiro.
However, Bad Bunny was not in attendance, continuing their noted separation over the past month. It was possible he had already returned to Puerto Rico for the holidays and time with family.
The night before, Jenner was at the Fontainebleau Las Vegas Grand Opening Celebration, wearing a sleek black dress with a halter neckline and corset bodice.
Then on December 16, The Messenger reported that a source claims the pair are officially broken up, and have actually split several weeks ago.
“There's no bad blood,” the insider claimed. “They are even still in contact. Their relationship had been rocky due to their busy schedules.”
The rapper will be going on tour in 2024, making it even harder to keep a potential relationship afloat, and Jenner “felt the relationship truly ran its course.”
January 2024
Us Weekly reported that Jenner and Bunny are seeing each other again on January 24, but they are not fully reconciled.
“Kendall’s friends aren’t surprised whatsoever that she’s seeing Bad Bunny again,” a source said. “They figured this would happen because she has a habit of going back to exes. It’s not the type of situation where they’re fully back together, but they have hung out a few times since breaking up last month.”
For Jenner’s friends, “at the end of the day, if she’s happy, then of course they support her and whoever she decides to date,” the insider added. “They’re still not convinced he’s The One for her, but if he treats her well then they’re good with it.”
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