Back in early 2023, Kendall Jenner and Bad Bunny 'broke' the internet after reports emerged about the pair dating, following months of speculation of her involvement with the singer, whose real name is Benito Antonio Martínez Ocasio.
Nicknamed the 'King of Latin Trap,' the Puerto Rican musician was first linked to the supermodel in February of that year, according to People, after being introduced by mutual friends. Since then, the duo has become the internet's latest celebrity 'it'-couple.
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Rumours started swirling about the pair's romance after Jenner broke up with her on-off boyfriend, NBA player Devin Booker, in late 2022.
Here's what we know about Kendall Jenner's boyfriend so far:
Kendall Jenner and Bad Bunny Double Date With Justin And Hailey Bieber, February 2023
Shortly after the rapper's move to L.A., he was spotted on a double date with Jenner and her friends, Hailey and Justin Bieber. The pair were apparently introduced by mutual friends, which led to them spending more time with one another.
Although only a fleeting moment of footage, paparazzi caught the pair leaving a restaurant with the Bieber's, according to this video posted on X.
Kendall Jenner and Bad Bunny Are Seen Kissing In Public, March 2023
Slowly solidifying the rumours, Kendall Jenner and Bad Bunny are seen kissing in public after being photographed by the paparazzi. TMZ posted the pictures following their sushi date with their friends and Jenner's younger sister, Kylie.
Kendall Jenner And Bad Bunny Watch A Lakers Game Together, May 2023
Not long after being photographed together at a Met Gala after party, Jenner and Bad Bunny attend a Lakers Game together and sit court-side with their friends, Yung Taco and photographer Renell Medrano.
Kendall Jenner And Bad Bunny Attend A Met Gala Afterparty Together, May 2023
Despite not appearing on the red carpet together, Jenner and Benito made headlines when they were pictured together at a Met Gala afterparty. Once the pair changed out of their respective Met Gala looks to the party the night away, they were spotted wearing more casual clothing.
Jenner's 1990s-inspired Marc Jacobs look alongside Bad Bunny's 1970s-inspired earth-toned outfit was nothing other than a true chef's kiss.
Kendall Jenner And Bad Bunny Go 'Instagram Official', August 2023
The singer shared a video to his Instagram Story, showing footage from one of the pair’s daytime excursions.
In the clip, a snippet of the couple’s conversation can be heard as Jenner’s legs appear in the shot standing in front a squirrel. Bad Bunny can be heard warning Jenner, saying: ‘Mami, be careful,’ to which Jenner replies, ‘Rabies?, which he responded to with, ‘Mosquitoes.’
In another video also posted to his Instagram story, Bad Bunny can be seen wearing a ‘K’ necklace, which eagle-eyed fans have noticed is the same one that Jenner has previously worn herself.
Kendall Jenner And Bad Bunny Make Their Front Row Debut, September 2023
Cementing themselves as a fashion power couple in the making, the rapper and supermodel were an unstoppable duo sitting front-row together at Sabato De Sarno's debut Gucci Show at Milan Fashion Week.
Bad Bunny kept things cool in a loose-fitted shirt, tailored jeans, and a beanie, whilst Kendall wore a trench coat, dark red leather heeled pumps and a matching handbag.
Kendall Jenner And Bad Bunny 'Hard Launch' Their Relationship With A Joint Gucci Campaign, September 2023
If there was ever an award for hard launching a relationship, Kendall Jenner and Bad Bunny may just take the cake. Shortly after appearing on the front row of Gucci's Milan show, the fashion house released a new campaign featuring the pair.
Kendall Jenner And Bad Bunny Reportedly Split, December 2023
After Jenner was last seen together with her boyfriend Bad Bunny, at an SNL after party, following his hosting of the show, it was reported by People that the duo had broken up, according to a close source. During this time, the pair hadn't been photographed since October, and Jenner was seen on solo outings in Aspen and Las Vegas.
Kendall Jenner And Bad Bunny Reportedly Reunite, May 2024
Following reports of the pair's split in December, fans of the couple are left thinking otherwise after Jenner and Bad Bunny are seen looking super cosy at a Met Gala after party. The duo look happier than ever as they laugh and talk over drinks with friends.
Kendall Jenner Is Seen Supporting Bad Bunny During His 'Most Wanted' Tour, May 2024
Despite the rumours of the pair allegedly no longer together, a video emerges of Jenner and Benito, arm in arm before his show at Miami's Kaseya Centre in Florida.
The video shows the two linking arms and engrossed in conversation, as they walk around the stadium before Bad Bunny's Most Wanted show.
A New Report Claimed Kendall Jenner And Devin Booker Decker Had broken up again, November 2022
People reports the pair went their separate ways in October 2022, with a source claiming: 'Both have incredibly busy schedules right now with their careers and they've decided to make that a priority,' they claimed.
'They have a lot of love and respect for each other and wish only the best.'
The pair have been romantically linked since 2020, but only went 'Instagram official' in February 2021.
In June 2022 it was widely reported the couple had split, but have been photographed together in recent months and have shared flirty comments on each other's Instagram photos.
Devin subtly shows adoration for Kendall when commenting under Kardashian-Jenner family photo
Booker Subtly Showed His Adoration For Kendall Jenner, October 2022
After Jenner's sister Kim Kardashian shared a promo shot of the family for their Hulu show The Kardashians, he took to the comments section to make his feelings for the supermodel known.
The photo featured Kendall at the centre of the shot, flanked by her sisters Kylie, Kim, Kourtney, and Khloé, as well as 'momager' Kris, and Booker simply commented: 'Middle.'
In the picture, Jenner is wearing a black sequinned one-shoulder dress and dewy make-up, with her hair down in an effortless, tousled style.
Fans have since reacted to Booker's comment. 'Finally,' one fan responded, seemingly referring to his first public display of affection since the couple's rumoured split and apparent reconciliation.
Kendall Jenner Posted A Carousel Of Pictures Of Herself Lounging In A Brown Bikini, August 2022
In the photos, which have received more than five million likes, she wears a baseball cap that shields her face, putting all the focus on her physique.
Devin Booker later commented on the model's bikini pics with a flirty hot face emoji.
We think it's safe to say this has only fuelled speculation that the couple are more than just friends, following news they reportedly split in June 2022.
Kendall Jenner tends to keep her private life under wraps, however the model took to her Instagram stories to share a holiday snap of herself and Devin Booker looking well and truly loved up.
The photograph seemingly reconfirmed that the couple are back on, after they reportedly split in June due to their 'very different lifestyles' (see below).
In the photo shared by The Kardashians star, she was perched on Booker's lap while drinking what looks to be a bottle of beer.
At the time, they were chilling out on a porch and their profiles were on show as they looked in the same direction.
Jenner was dressed in an oversized shirt and shirtless Booker wore blue shorts.
Jenner seemingly confirmed that she and booker had rekindled their romance, after much speculation surfaced since their reported split in June 2022.
This was after the model shared footage of the basketball player to her Instagram stories.
Booker could be seen in a field enjoying a vacation with the Keeping Up With The Kardashians alum.
In the clip, Booker threw an axe at a tree while in a scenic area.
As per the Daily Mail, Jenner and Booker had been enjoying zip lining and hiking in the mountains.
This came after a source told E! News: 'She and Devin are fully back together.
'They worked out their issues and decided they want to move forward and be together.
The source added: 'They moved on and it's going really well,' saying the couple have been 'spending a lot of time together' and even went to a wedding together.
'Devin was her date to her friend Lauren's wedding over the weekend in Napa,' the insider said.
Over the weekend, Jenner shared a snap of herself in the arms of a man whose head was cropped out, and it turned out the mystery man was Booker, the same news outlet reported.
On July 17, Jenner shared footage of herself posing for a mirror selfie while seemingly getting ready for a night out, but it was the sudden appearance of a man's arm that got us in a bit of a frenzy.
The man who video bombed her later appeared again, only this time he was stood behind the model and had wrapped one arm around her waist, while she was dressed in a floor-pooling shirred gown.
We think it's safe to say the mysterious man, dressed smartly in a tuxedo, was probably Booker.
Both Jenner and Booker's faces were hidden in the shot, taken by the model on her iPhone.
All that was left to ask was: are they back on?
Kendall Jenner shows her support for Devin Booker by sharing his NBA 2K23 video game cover
Following speculation that Jenner and Booker have rekindled their romance, the model gave fans of the couple more reason to stay hopeful.
She re-shared an image of basketball player Booker's NBA 2K23 video game cover, but didn't write an accompanying caption.
Booker had originally posted the photo to his Instagram feed, which showed him dribbling a ball, with his profile on show.
Kendall Jenner And Devin Booker Spark Reconciliation Rumours, July 2022
After news surfaced in June that Jenner and Booker had broken up, photos obtained by Page Six showed them looking affectionate at Soho House in Malibu on July 26.
The photos may well have just meant the pair were simply friends with history, as an earlier US Weekly report quoted a source saying the duo were 'still super amicable and supportive of each other'.
Jenner is known for being fiercely private about her love life, so at this point, only time would tell whether or not they were still an item.
A Difficult Realisation Led To Kendall Jenner And Devin Booker's Split, June 2022
A source told E! News that Jenner and Booker faced a challenging time after attending Kourtney Kardashian and Travis Barker's wedding together.
'They had a really nice time in Italy together,' the insider said. 'But once they got back, they started to feel like they weren't aligned and realised they have very different lifestyles. Kendall told Devin she wanted space and time apart.'
Despite their split, however, the pair were understood to be on good terms.
'They have been in touch since and do care about one another,' the source added. 'They both hope to make it work but, as of now, they are split.'
Kendall Jenner Reportedly Splits From Devin Booker, June 2022
Jenner had reportedly broken up with NBA star Booker, after a two-year romance.
However, a source told Entertainment Tonight that there was a possibility for a reconciliation.
'Kendall feels like they're on different paths,' the source said. Another insider claimed the pair 'have had discussions about their future but they are not on the same page'.
Kendall Jenner Gives Rare Insight Into Private Life, Confessing She’s Been In ‘Toxic Relationships,' May 2022
Despite Jenner remaining relatively private about her personal life, the supermodel opened up about her 'toxic relationships' on episode six of Hulu show The Kardashians.
While she didn't reveal any names, she brought up her past while reliving her altercation with Scott Disick to sisters Khloé and Kourtney Kardashian.
In the previous episode, Jenner was seen storming off from an argument with Kourtney's ex Disick, who was upset that she didn't invite him to her birthday celebration.
Referring to Disick, Jenner explained to her sisters: 'He's talking through me the whole time and I'm like, "I don't do that." I've been in enough toxic relationships and I can't stand it anymore, so I just shut off.'
She admitted in a confessional that Scott was 'victimising himself, he was villainising everybody else, including me, which I have no ill intentions towards him and I love him and I always want him around. It just caught me off guard.'
Jenner and Disick later made up.
As for her 'toxic relationships' she didn't shed further details, and the model was yet to discuss Booker on the Hulu series.
Kendall Jenner Reveals Her Phone Lock Screen Photo Of Devin Booker, May 2022
Jenner gave a rare glimpse into her relationship with Booker when promoting a new episode of Hulu's The Kardashians.
Alerting fans to the May 5 episode, she shared a screenshot of her phone that showed a reminder to watch, but it was the black and white photo on her locked screen that caught the media's attention.
The image was of her beau Booker wearing an NBA jersey with his name on the back.
Though it shows just a hint of his profile, it suggested he's the first person she sees whenever she picks up her phone.
The image (which you can see here) was shared to her Instagram stories, with a message that read: 'A new episode of The Kardashians is now on Hulu.'
Kendall Jenner Talks About Supporting Devin Booker At 'Every' Game During Rare Interview, April 2022
Jenner spoke about Booker during her and the family's interview on Jimmy Kimmel Live!, which took place on the same day she went to her NBA player beau's game.
The supermodel actually told Kimmel that she watches all of Booker's games.
'Of course [I do]. I watch every game unless I have—last night I had a dinner but all my friends and family know that I like sit with my phone wherever I am,' she explained.
'Yeah, [I became a sports nut because of this]. I’ve always been a fan of basketball since basically with Khloé [Kardashian. Kendall’s older sister], I remember we used to go to all the Lakers games when I was really young so I’ve been a huge fan of the NBA for a really long time.'
Devin Booker And Kendall Jenner Aren't In A Rush 'To Settle Down,' March 2022
Jenner and Booker's relationship appeared to be blossoming, but the pair were in 'no rush to settle down', according to a source close to Jenner.
Speaking to E!, the source revealed that getting engaged wasn't in the couple's near future, saying: 'Kendall and Devin’s relationship is going strong, but they are in no rush to settle down and tie the knot.'
The source continued: 'Kendall is not a conventional or traditional type of girl and doesn’t even care about having a huge elaborate wedding.'
'She is very much content with how things are with Devin right now.'
With regards to the pair's day-to-day relationship, while they spent a lot of time apart due to their careers, this suited the fashion model who is a 'very independent woman', the source added.
Still, this didn't stop them from being romantic. 'Devin likes to do little things for Kendall to make sure she is appreciated and loved and it warms her heart.
'They have a sweet relationship, and the family loves seeing them together and seeing her happy,' the source explained.
Devin Booker Discusses Kendall Jenner Relationship, March 2022
Booker opened up for the first time in an interview about dating Kendall Jenner.
Speaking to WSJ magazine, Booker responded to a question about what it's like dating someone in the the spotlight, noting: 'I wouldn’t say [it’s been] hard.
'Honestly, I’m enjoying life to the fullest, and that came off my tongue so easily because it wasn’t always this way, but I feel like I’m in a good place right now. I love my family, I love the people around me, and I love the impact that I get to have on this world, the younger generation under me and the kids who look up to me.'
Kris Jenner Discusses Kendall’s Future As A Mum, February 2022
Jenner appeared on The Ellen DeGeneres Show on February 17 and opened up about her daughter Kendall Jenner's future as a mother.
When asked by DeGeneres about the possibility of a 12th grandchild, Jenner said: 'I think it would be nice if it was Kendall, right? She’s the only one who hasn’t had a baby.'
The TV host then questioned the model's desire to have children and asked: 'Does she want to have a baby?'
The 'momager' then enthused: 'I think she would eventually love to have a baby.'
Devin Booker Sparks Marriage Rumours, January 2022
Booker was seen wearing a gold band on his left ring finger in a selfie Jenner shared to her Instagram account, sparking rumours that the pair have secretly married.
The image causing a stir was one of a series of photos posted by the model, accompanied by the caption: 'my weekend'.
The photograph, which showed the couple snuggled up and posing in front of a mirror, appeared to be from her and Booker's serene, rural weekend getaway.
One follower wrote: 'He's wearing a wedding ring?' and another commented: 'Anyone else notice the ring on his hand ?????? [sic]'
This wasn't the only speculation to come from this series of photos posted by Jenner. Others alluded to the possibility of her being pregnant.
One wrote: 'Congratulations on your pregnancy,' with another writing: 'Oh my god, I thought it was a pregnant announcement [sic].'
This came after Jenner said: 'I want kids badly. Soon too,' during the final season of Keeping up with the Kardashians, after reflecting on being the odd one out due to all of her siblings being parents.
Speculation aside, sister Kourtney Kardashian commented under the post: 'Cute weekend!'
Devin Booker Pays Tribute To Birthday Girl Kendall Jenner, November 2021
Days after the model called her boyfriend her 'best friend' on his birthday, the athlete celebrated Jenner's birthday on Instagram, and it became clear he was head over heels for the star.
'Most beautiful woman,' he captioned a candid photo of Jenner. In another post the couple share a loving embrace.
Devin Booker Kisses Kendall Jenner Publicly For The First Time, October 2021
While Kendall Jenner may have spent most of the LA Lakers vs Phoenix Suns game third wheeling alongside married pals Hailey and Justin Bieber, her boyfriend Devin Booker came over to greet her at the close of the game.
In a super rare moment of PDA the NBA player planted a kiss on the cheek of his model partner, making the crowd go wild (we're the crowd).
Kendall Jenner Claps Back At Devin Booker's Halloween Taunt, October 2021
Kendall Jenner responded to her boyfriend Devin Booker's jibe on Twitter after he made fun of her pumpkin carving skills.
Jenner had taken to her Instagram Stories to share photos of the pair's pumpkin carving evening.
However, Booker later took to 'take the Michael' out of his girlfriend's carving attempt, tweeting: 'Pumpkin don't count if you used a stencil.'
'I feel personally attacked,' Jenner responded, before receiving support from her fans who agreed that her pumpkin carving was better than the basketball player's.
Kendall Jenner Shares Holiday Pictures With Devin Booker, September 2021
Sharing photos from the aforementioned Italy holiday - which featured boat rides, pasta and Y2k style - Jenner confirmed that all is happy and lovely in her relationship with basketball player Booker.
The montage of photos showed the couple walking down a cobbled street and joined by friends including Fai Khadra on the trip:
Taking to her Instagram Stories, Jenner shared a more personal selection of photographs, which showed her cuddling up to Booker for the camera, against a backdrop of a beautiful Italian mountain after sunset:
Kendall Jenner And Devin Booker On Holiday, August 2021
Continuing with Booker's post-Olympics R&R, Jenner and her basketball player boyfriend were photographed on holiday in Italy.
In the photos, Jenner effused serious 1990s Jennifer Lopez tribute style wearing a yellow bandana around her hair, oval tortoiseshell sunglasses, a white crop top and green maxi skirt.
Meanwhile, Booker wore a yellow short-sleeved shirt with a white tee underneath.
The couple boarded a boat for a cruise around the Mediterranean before disembarking to meet friends for lunch in the sunshine.
Us, jealous? Never.
Kendall Jenner Wears Devin Booker's Olympic Medal On Holiday, August 2021
At the time, pictures showed Devin Booker unwinding from his Olympics mission to Tokyo in the most tranquil, yet equally, fun way.
Sharing a series of photos from a lake holiday he took with girlfriend Kendall Jenner (and his beloved dog) since returning from Japan, one included a chill photo of a bikini-clad Jenner celebrating her beau's achievements by wearing his Olympic gold medal and sipping a beer.
A mood.
Team USA beat France to win gold in the basketball final on August 7, 87 to 82 points.
Booker in the Olympic final
Kendall Jenner Publicly Confirms She's Dating Devin Booker In Interview, June 2021
To mark the end of Keeping Up With The Kardashians, the famous siblings sat down with Andy Cohen for a tell-all interview in what's been dubbed 'the reunion'.
During part two of the reunion, Kendall was asked about her private life - which is rarely seen on the show, especially in comparison to the romantic lives of her elder sister Kourtney, Kim and Khloe.
Reportedly referring to basketball player Booker as 'my boyfriend' for the first time, Kendall joked, per E! News: ' No, I don't actually only date basketball players, if anyone's ever done their research... I'm not ashamed that I have a type, and I'm also a genuine basketball fan.'
The model then explained that having grown up in the public eye, both Kendall and Kylie have decided to keep their relationships largely private after witnessing their elder sister's experiences.
'I think it makes my life a lot easier and our relationship a lot better, to be honest...I just feel like it's a private matter and not for anybody else to judge or know,' the 25-year-old said.
KUWTK Producer Explains Kendall Jenner's One-Year Dating Rule On Show, June 2021
A producer from Jenner’s show Keeping Up With The Kardashians explained why fans never got a look in at the model’s romances.
Executive producer Farnaz Farjam opened up on Bravo’s The Daily Dish podcast and noted: ‘Kendall’s always had this rule – she felt like she had to be with someone for at least a year before she let them be a part of the show, because she doesn’t always know what people’s intentions are. So that’s why we kind of kept her personal life out of it, just because she had a rule.'
Meanwhile, when it came to Jenner’s sister Kylie’s relationship with Travis Scott, with whom she co-parents three-year-old daughter Stormi – Farjam said that the rapper ‘didn’t really want to participate’.
'I feel like Kylie became more participatory this last season towards the end, and Kendall has dipped in and out,’ she explained. ‘But they were at an age ... like, if you think about when you're a young adult coming into adulthood, I think you sometimes care a lot more what the outside world has to say about you.
'[Kylie] did share her relationship with Tyga. We showed their relationship quite a bit on Keeping Up, and then Travis [Scott] didn't really want to participate.'
Kendall Jenner And Devin Booker Celebrate First Anniversary, June 2021
The couple marked their first anniversary together over the weekend and revealed that they became a couple in June last year during the Coronavirus pandemic.
On Saturday, the model and NBA player shared several photos on their respective Instagram accounts of each other to mark the special day.
One photo on Jenner's account reportedly showed the pair cuddled up with a dog, while another saw the couple hugging, according to PEOPLE. On the basketball player's account, the 24-year-old posted a picture of the couple together with the captioned '365' and another with '52, making the days and weeks they've been in a relationship, respectively.
The couple were first rumoured to be an item in April 2020 and went Instagram 'official' on Valentine's Day earlier this year.
Kendall Jenner And Devin Booker Seen On Date Nights, April 2021
Over the weekend, Jenner and Booker spent some quality time together, as they were photographed heading to restaurants and out for the day in New York City.
On April 24, the couple were seen in the SoHo area of the city, with Jenner wearing a cream cardigan with black stitching by Korean brand TheOpen Product.
That evening they were seen holding hands and heading out to dinner at Carbone restaurant, with Jenner wearing a tan-coloured leather-look bandeau top and trousers and Devin keeping it casual in an open check shirt and beige trousers in photographs obtained by People.
On the Monday, Jenner was seen at Booker's basketball game, where the Phoenix Suns played the New York Knicks in Madison Square Gardens, which she attended with fellow model Joan Smalls.
Kendall Jenner Shuts Down Pregnancy Speculation, March 2021
Jenner's 'momager' Kris Jenner got the rumour mill into motion when she shared a motivational tweet to her daughter, followed by a baby bottle emoji.
Jenner soon responded to the tweet and subsequent online speculation that the emoji might suggest she's pregnant, tweeting her mother: 'Mum, this looks like a pregnancy announcement' following by a crying and a 'palm in face' emoji.
In 2017, Jenner similarly responded to pregnancy rumours online after sharing a photo of herself wearing a tight polka dot dress.
The supermodel later tweeted a publication which suggest she might be pregnant, noting: 'I just like bagels ok!!! [sic]'
Kendall Jenner Goes 'Instagram Official' With Devin Booker, February 2021
On Sunday (Febraury 14), Jenner shared a photo of herself lying back on a kitchen countertop laughing and smiling while Booker - whose face couldn't be fully seen - embraces her. Sharing the image with her 151 million followers, Jenner accompanied the picture with a simple heart-shaped emoji.
Over on his Instagram page, Booker shared a video of Jenner playing with a dog at sunset which he captioned with a heart emoji, as well as a black and white photograph of himself, Jenner and the dog relaxing on a blanket on the grass.
Devin Booker Shares Photograph Of Kendall Jenner, January 2021
Valentine's Day wasn't the first time Booker had publicly acknowledged being with Jenner. In January, the basketball player shared a photograph of Jenner sunbathing to his Instagram Stories commenting 'whew', according to E!.
Devin Booker And Kendall Jenner Celebrate Kim Kardashian's Birthday, October 2020
Eagle-eyed fans noticed Booker with Jenner in the background of photos from Kim Kardashian's infamous - and widely criticised and mocked - lavish 40th birthday celebrations on a private island (which took place during a global pandemic).
Kendall Jenner And Devin Booker Spotted Out For Dinner, August 2020
The couple were photographed heading to dinner in Santa Monica, California days after another sighting outside a pet shop together and with Jenner's sister Kylie also heading to dinner at celebrity favourite Nobu, Malibu, People reported.
Kendall Jenner And Devin Booker First Linked, April 2020
The 25-year-old supermodel and Booker first landed on the rumour mill when they were reportedly spotted together in Arizona in April. It was following this that Jenner then executed a brilliant clapback on social media in response to a follower's sexist joke referencing other basketball players Jenner had been subject to relationship rumours with in the past.
Kendall Jenner's Style File
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