Of all their many star-studded relationships, Kendall Jenner and Bad Bunny feel like the one that got away — and keeps coming back. Few couples have drifted in and out of headlines quite as persistently, or as intriguingly, as this pair.
At the 2026 Super Bowl, Bad Bunny took to the stage for a show-stopping performance — a celebration of Latin music, Puerto Rico and love itself. And speaking of love, Jenner was right there in the audience, watching on from her VIP box.
So where does the couple stand now? What is the complete Kendall Jenner and Bad Bunny relationship timeline? And how did these two seemingly unexpected stars cross paths in the first place?
Let’s dive in.
From speeches to pins, the artists spoke loud and clear.
Kendall Jenner and Bad Bunny relationship timeline
Jenner is fresh off a breakup with NBA star Devin Booker when she is first linked to the rapper.
Bad Bunny and Jenner are spotted seemingly heading out on a double date with Justin and Hailey Bieber, with all four photographed leaving the same Los Angeles restaurant together. Friends already in the mix?
Shortly after, a source close to the pair tells People that the two “are spending time together.”
“Kendall recently started hanging out with him,” another insider adds. “They were introduced by friends. He moved to L.A. a few weeks ago and bought a house.
“She likes him and is having fun,” the source continues. “He is different from guys she has dated in the past. He is very charming.”
The new couple were spotted out in West Hollywood in early March, enjoying dinner with friends. Onlookers reported that the pair shared a hug — and possibly a kiss — before parting ways.
That same month, a source told Us Weekly that Jenner wasn’t “really looking to date anybody.” Still, the insider added: “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.” According to the source, 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,” the insider continued. “Kendall appreciates how he treats her with respect and that he makes her laugh. He’s very charming, and she thinks he’s a great guy. Although things are still fairly new, she definitely sees potential.”
By the end of March, fans began speculating that Bad Bunny had all but confirmed the romance in his music. On Eladio Carrión’s track Coco Chanel, he appears to reference a new love interest, rapping: “I’m not bad, baby, that’s a gimmick / But the sun in Puerto Rico is hotter than in Phoenix / She knows it.”
For context, Jenner’s ex Devin Booker plays for the Phoenix Suns. Elsewhere on the track, Bad Bunny also gives a nod to “Scorpio women” — Jenner’s star sign.
Soon after, the pair were spotted out at dinner once again, with an eyewitness claiming they were “openly kissing” and “being very affectionate.”
Now for the photos that changed the course of history — at least for us. The couple were spotted horseback riding together, instantly cementing their status as an unexpected romance for the ages. Bridgerton season two energy, anyone?
On 15 April, Jenner watched Bad Bunny’s Coachella performance in Indio, California, and was captured dancing in the crowd in a TikTok that quickly made the rounds online. Later that weekend, she was also photographed by his side as he leaned in to whisper to her amid the festival chaos.
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The sightings continued. On 26 April, the pair were spotted together at Tyler the Creator’s concert in Los Angeles.
Just days later, on 29 April, they were seen in New York City heading to Carbone, the celebrity-favourite hotspot, before moving on to Pergola for after-dinner drinks. The night ended with the two leaving together in a blue Mercedes — very couple-coded behaviour.
The couple didn’t walk the Met Gala red carpet together (we know, it's devastating). However, they did attend an after-party side by side.
That same day, a source told People that the relationship 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 insider 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.”
Then came the vacation, because that’s when things officially feel real. Jenner and Bad Bunny travelled with friends, a trip briefly revealed via TikTok when photographer Renell Medrano posted a video featuring the pair together. Although the clip was quickly deleted, screenshots of the moment continue to circulate online.
Another source told Us Weekly that same 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.”
The insider added that Jenner is “really attracted” to his confidence — and honestly, can you blame her?
“They’re 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.”
The following day, the couple were spotted sitting courtside at a Lakers playoff game in Los Angeles. We’d be remiss not to mention Jenner’s knee-high snakeskin boots — matched, no less, by Bad Bunny’s white snakeskin pair. Coordinated, but make it chic.
By 24 May, a source told Entertainment Tonight that the relationship was continuing to deepen. “He is not only spending more time with Kendall, but with the rest of the family as well,” the insider revealed.
There is “potential” for the romance to be more “long-term,” the source added. “They’re both always laughing and smiling together and have similar family values.” Jenner, meanwhile, is said to be enjoying their low-key relationship — and is excited about where things are headed.
Finally, we hear from the happy couple themselves.
When asked about Bad Bunny, Jenner told WSJ Magazine she had “no comment.”
“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.”
Bunny echoed the sentiment to Rolling Stone, reflecting on the importance of shielding his personal life. “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 rumours about his relationship with Jenner, he reiterated: “That’s the only answer. In the end, the only thing I have is my privacy.”
Another vacation together! A source told People that Jenner and Bunny escaped to Gozzer Ranch Golf & Lake Club in Harrison, Idaho.
The insider described the pair 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.”
Back in West Hollywood, the couple were spotted enjoying a dinner date at Sushi Par on 27 July — a favourite spot they’ve been photographed at before.
That same day, on an episode of The Kardashians, Jenner revealed a very telling gift from her mom, Kris. She shared that Kris had given custom dollhouses to all her siblings for Christmas — and decorated hers with an engagement ring.
“She put an engagement ring in mine, because she thought it was manifesting an engagement for me,” Jenner said in a confessional. “So if that tells you anything about where my mom wants me to be in life.”
PDA alert! Videos and photos surfaced of Jenner and Bunny kissing at Drake’s Los Angeles concert, marking one of their most affectionate public outings since they began seeing each other. This date night had fans swooning — and gave us all serious couple goals.
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Then came the Instagram soft launch — about time, right? Bad Bunny shared a video featuring a woman he referred to as “mami,” whose voice fans quickly noticed resembled Jenner’s. He also subtly flexed the connection, wearing a “K” initial necklace in one snap and including a photo of her 818 Tequila line in another.
The couple’s string of public appearances continued, including outings at the Met Opera in New York City and Gucci’s fashion show in Milan.
In mid-September, Vanity Fair published a profile in which Bad Bunny opened up about why he keeps his romance with Jenner so private.
Addressing fans who disapprove of their relationship, 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.”
He continued:
“There are people who say that artists have to put up with it. 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.”
Bunny also revealed he isn’t ready for traditional relationship milestones just yet. When asked about weddings and kids, he replied, “No, I don’t think so,” adding — at least “not now.”
He also clarified that he improved his English for someone specific.
“With some people, I speak English — with some specific people,” Bad Bunny said. “With one of them, I couldn’t talk to her before.”
Finally, the couple made their first official collaboration public. Shortly after their appearance at Gucci’s show, Jenner and Bunny starred together in the fashion house’s newest campaign, which launched on 30 September — giving fans a glimpse of the power couple in full-on haute couture mode.
Hand in hand, they attended an SNL afterparty.
Ahead of Bunny’s SNL appearance on 21 October, the artist appeared to subtly reference his romance with Jenner in his promo. In the video, Bunny squashes a mosquito, captioned simply: “be careful.”
Fans quickly connected the nod to an August Instagram Story, in which he told Jenner, “mami, be careful,” while hiking to avoid mosquitoes. That clip, part of his soft launch of the relationship on social media, didn’t show Jenner on camera, but her voice could be heard.
Jenner joined him at the SNL after-party at L’Avenue, keeping the public appearances rolling.
A week later, on 29 October, the pair were photographed brunching at the Beverly Hills Hotel, following Jenner’s Halloween party the night before. An eyewitness told TMZ they were “being cute and affectionate” — adding another chapter to the couple’s ongoing public PDA parade.
Trouble in paradise? On 14 November, Jenner shared an Instagram post of a sunset with the caption: “what’s meant for me, will simply find me.” Cue the breakup speculation. Yet, no reports emerged suggesting any issues between Jenner and Bunny, and neither addressed their relationship publicly.
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Two days later, a source told Us Weekly that Jenner’s friends weren’t entirely convinced the romance would last.
“Kendall’s friends don’t think she’ll be with Bad Bunny forever,” the insider said. “Despite the breakup rumours, 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.”
On 14 December, Jenner attended the Revolve + FWRD Pop-Up Shop party in Aspen, Colorado, solo. Her 818 Tequila was on the menu, and she spent the evening mingling with guests, including Devon Windsor, Raissa Gerona, and Lais Ribeiro.
Some fans speculated about Bunny’s absence, while others assumed he may have already returned to Puerto Rico for the holidays and family time.
Just two days later, The Messenger reported that a source claimed the couple had officially split — and that the breakup had actually occurred several weeks prior.
“There's no bad blood,” the insider said. “They are even still in contact. Their relationship had been rocky due to their busy schedules.”
With Bad Bunny scheduled to go on tour in 2024, the source added that Jenner “felt the relationship truly ran its course.” Oh, mami!
Even celebs enjoy a backslide, not that we're complaining. On January 24, Us Weekly reported that Jenner and Bunny are seeing each other again, but haven't gone full-blown reconciliation.
“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.”
On May 6, the former couple were spotted together at the Après Met 2 Met Gala after-party, looking like they were on good terms.
A week later, a source told Entertainment Tonight that Jenner and Bunny were still making time for each other whenever possible.
“Kendall and Bad Bunny are still in contact and spend time together when they can,” the insider said. “There’s a strong connection between them whenever they’re together, and they have the same chemistry that they’ve always had.”
The source added, “They’re having fun for now, but are hoping to figure things out in a way that makes sense. They’re not necessarily back together or exclusive, but there is definitely still a vibe between them. Neither of them feels any pressure, and they appreciate that they can enjoy space when they want. It’s casual, easy, and comfortable between them.”
On 17 May, Jenner was spotted at Bad Bunny’s concert in Orlando, Florida. Fans shared TikToks of the Kardashians star in the VIP section, wearing a black hoodie from Bunny’s Most Wanted tour, dancing and chatting with friends throughout the show.
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A week later, on 24 May, the pair were seen leaving a private dinner at Gekko Japanese Steakhouse in Miami after his concert. According to an eyewitness speaking to TMZ, they dined in a VIP room for “about an hour and 20 minutes” before leaving just after midnight in the same SUV. While the source noted there were no “outward signs of affection,” they still “seemed to be a couple.”
Finally, on 30 May, People confirmed that Jenner and Bad Bunny were officially back together.
“It’s going well, and they’re prioritising spending time together as they figure it out. There wasn’t ever any drama in their breakup, and they missed each other,” one source said.
Another added, “They had initially broken up because they were not on the same page in life. It’s like they needed the break to miss each other enough to figure things out. They always had this crazy attraction to each other. Things are great again.”
The reunited couple were spotted enjoying a romantic dinner at Yoko Japanese Restaurant in Puerto Rico, captured in a short clip shared by TMZ. In the video, Bad Bunny could be seen talking enthusiastically while Jenner listened attentively.
By 23 June, the pair had touched down in Paris, where they were photographed getting a little handsy as they left Ferdi restaurant.
The next day, 24 June, they enjoyed another dinner at La Girafe, also in Paris. Dressed in matching black outfits, Bunny held onto Jenner’s arm as the couple exited the restaurant, exuding that effortless, high-fashion romance.
On again, off again. The couple quietly called it off once more, this time with no Instagram hints to signal the split. A source told Us Weekly on 25 September that the two are “still friendly but have taken a step back and aren’t dating.”
“[They] were more serious after their short break earlier this year,” the insider added. “But it ultimately didn’t work out long term.”
The source noted that Jenner was the one who “decided she wanted space” following their European summer getaway.
Meanwhile, Bunny has reportedly returned to dating apps, Raya in particular, signalling he’s ready to meet someone new.
On 7 February, Jenner hit the runway for Calvin Klein at New York Fashion Week, and Bad Bunny was spotted sitting in the front row watching her walk. If he was bothered by being so close to his ex, he certainly didn’t show it.
Some fans even think Bad Bunny threw subtle shade at his ex after one of his Instagram photo dumps — pointing to a snap of a baseball cap that read, “Stop dating people who don’t get your music.” Followers were quick to link the message to Jenner, given their on‑and‑off history and her being less connected to his Spanish‑language world, though neither Bad Bunny nor Jenner commented on the speculation.
On 8 February, Jenner watched Bad Bunny’s Super Bowl LX Halftime Show from a VIP box surrounded by friends — but the pair weren’t seen interacting that evening, even as cameras caught her enjoying the performance.
We'll let you know if we hear more about Kendall Jenner and Bad Bunny, who are currently not linked to anyone new.
