Kendall Jenner and Bad Bunny Are a Front-Row It Couple at Milan Fashion Week

Kendall Jenner and Bad Bunny caused a stir in February with their unexpected romance—and months later, they are still going strong.

The supermodel—who previously dated NBA star Devin Booker—first connected with the Grammy-winning Puerto Rican rapper through mutual friends when he moved to Los Angeles earlier this year. The pair have since embarked on a low-key though buzzy romance, as reflected in both their joint sighting at this year’s Coachella and their date nights around Los Angeles.

Ahead, see everything we know so far about the model and rapper’s blossoming relationship—from the first dating rumors to their most recent outings.

September 22, 2023: They make their front-row debut at Milan Fashion Week.

The couple attend Gucci’s Spring/Summer 2024 runway show in Milan, Italy, where they sit front-row together in cool looks. Jenner is dressed in a pale beige double-breasted trench coat as a minidress, cinched at the waist with a matching belt. She completes the look with crimson pointed-toe slingbacks, a Jackie shoulder bag in the same hue, sculptural gold hoops, and black rectangular sunglasses. Meanwhile, Bunny wears a crisp white button-down, blue jeans, black dress shoes, a beige beanie, diamond hoop earrings, and his own pair of black shades.

milan, italy september 22 bad bunny and kendall jenner are seen at gucci ancora during milan fashion week on september 22, 2023 in milan, italy photo by jacopo m raulegetty images for gucci
Jacopo M. Raule - Getty Images

September 15, 2023: They spend the day together in NYC.

The singer and the model are spotted out and about together in NYC, where they look cool in casual looks on an afternoon stroll. That evening, they enjoy a dinner at celeb hotspot Cosme, where Jenner styles a pair of gray jeans with an oversize, floral-print knit sweater. She completes the look with black loafers, sunglasses, and a huge tan bag. Bunny wore a white button-down over a white tank top and baggy jeans, adding a brown leather belt, a blue ball cap, and layered necklaces.

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September 12, 2023: Bad Bunny speaks out on fans criticizing his romance with Kendall.

In a candid interview with Vanity Fair, the musician gets real about enforcing personal boundaries when it comes to his private life and fame.

“They [fans] 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,” he tells the magazine. “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 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, I have nothing I need to clarify to her. Never. About anything.”

He adds, “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.”

He also lambasts the culture of people normalizing the filming of strangers in public spaces.

“It used to be a guy with a camera and a flash and they fuck with your eyes like that. Nowadays, everybody is a paparazzo,” he says. “Everyone is taking photos, everyone is recording. Nobody respects anybody’s privacy, and not only my privacy as a celebrity, but yours.... Because if right now you go out there and your pants are ripped and you can see a butt cheek, or a pigeon shits on you, there’s a bastard who will film you and take a picture of you.”

August 28, 2023: Bunny wears Kendall’s K initial necklace.

Benito once again subtly showed his love for Jenner on his Instagram Story by wearing a dainty gold chain necklace with a K charm. The necklace appears to be the same one the model wore during a recent video interview.

August 27, 2023: Bunny posts a rare video with Kendall.

On his Instagram Story, the rapper shares a rare clip of an intimate moment with his girlfriend—in it, Jenner is heard calling to a little squirrel who is running in the bushes next to them. “It’s the cutest thing ever. Come here!” she says. “Mami, be careful,” Bunny tells her. “Rabies?” she asks. “The mosquitoes,” he replies.

The pair’s faces don’t show in the video, but the sweet back-and-forth conversation is the most we’ve gotten from them in terms of insight into their dynamic.

And in another subtle tribute to Jenner, the “Where She Goes” rapper also posts a photo on his Story of two cocktails—presumably his and Jenner’s—next to an 818 tequila bottle, which is the model’s brand. No caption needed.

bad bunny instagram
Bad Bunny / Instagram

August 13, 2023: They make out and dance at a Drake show.

The couple look so in love while at Drake’s concert in Los Angeles on Sunday. A video shared by a concertgoer on TikTok shows Jenner and Bad Bunny making out, sweetly embracing, laughing, and dancing to the music. What makes it all hilarious, though, is that the model’s older sister Kim Kardashian is standing right beside Bunny the whole time.

July 31, 2023: They match in dark outfits for a date.

Jenner wears an asymmetric black mesh top over a lacy black bralette for a date with the rapper. He, meanwhile, opts for a cool black tank and brown leather jacket.

bad bunny and kendall jenner

July 26, 2023: They coordinate looks for a sushi date.

The singer and the supermodel step out for dinner at Sushi Park in West Hollywood in all-black looks. Jenners opts for a chic black midi dress with spaghetti straps and a matching black leather mini shoulder bag. Bad Bunny looks cool in a dark-wash denim jacket layered over a black top and paired with black pants. He accessorizes with a black baseball cap—which he wears backward—black oval sunglasses, and gold jewelry.

kendall jenner and bad bunny

July 20, 2023: Kendall and Bad Bunny are reportedly “becoming more serious.”

While Jenner and Bad Bunny have kept their romance private, the couple are reportedly getting closer than ever. A source tells Entertainment Tonight the pair are getting closer as they keep things light and continue dating.

“Kendall and Bad Bunny are still hanging out and having a great time with each other. Things are definitely progressing between them,” the source says. “Things are becoming more serious and their relationship is on the upswing. They are still keeping things light, but they are both super into each other and have a ton of chemistry. Their friends and families are really happy for them and like them as a couple.”

June 21, 2023: The two publicly allude to their relationship for the first time.

In new interviews, the couple open up about keeping their romance out of the spotlight.

Speaking with WSJ magazine, Jenner has “no comment” when asked about her relationship status. She explains, “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. 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.”

Bad Bunny echoes the model’s sentiment in an interview with Rolling Stone. “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,” he tells the outlet. “That’s the only answer. In the end, the only thing I have is my privacy.”

He adds, “We’re in the worst time, the worst moment for the privacy of other humans; not just artists, but human beings. Today, no one respects the privacy or life of anyone. … I keep living. Fans are always going to want to know more, but I don’t focus on that. I’m always going to keep living my way.”

June 20, 2023: They coordinate outfits during a night out with friends.

While getting sushi with a group of friends, Jenner and Bad Bunny both wear white T-shirts. Jenner pairs her shirt with black-and-white snakeskin pants, a black bag, and square-toe boots. Bad Bunny coordinates his tee with off-white trousers with a light gray print and a camouflage trucker hat.

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Getty Images

May 14, 2023: They show off their couple style on a dinner date.

The model and rapper embark on a dinner date in Santa Monica, where the two coordinate in black leather ensembles. The model pairs a black leather trench coat with pointed-toe kitten-heel mules, and accessorizes with a black-and-yellow croc-embossed Fendi purse. The rapper, meanwhile, wears a black leather collared jacket with leather trousers and chunky square-toe boots, topping off the look with a backward baseball cap and red-tinted shades.

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May 12, 2023: They have their first public outing at a Lakers playoff game.

Jenner and Bad Bunny make a buzzy appearance at Arena, where they sit courtside for the Lakers-Warriors playoff game while wearing coordinating snakeskin-print boots. They are seen smiling and chatting closely together throughout the game, with the rapper occasionally resting his arm on the model’s seat.

For the outing, Jenner wears a casual white tank top and a dyed brown skirt with knee-high tan stiletto boots and gold jewelry. Meanwhile, the rapper pairs his pointed-toe boots with a black leather jacket, a white shirt, black pants, and a bolo tie with a silver bull pendant. He adds sunglasses and a baseball cap worn backward.

los angeles, california may 12 kendall jenner and bad bunny attend the western conference semifinal playoff game between the los angeles lakers and golden state warriors at cryptocom arena on may 12, 2023 in los angeles, california photo by kevork djanseziangetty images
Kevork Djansezian - Getty Images

May 1, 2023: They both attend the Met Gala, then make a date night out of the after-party.

Jenner and Bad Bunny are among the night’s attendees at the 2023 Met Gala, where Jenner wears a glittering black bodysuit by Marc Jacobs and Bunny wears a white tweed suit with a rosette cape by Jacquemus. Although they don’t make a joint appearance at the event, they are later seen heading into the after-party together.

For the occasion, Jenner wears a shimmering Nensi Dojaka playsuit—a replication of a 1994 Chanel creation, consisting of pearl-embellished spaghetti straps, plus a black thong and an ultra-cropped black tank layered over the piece.

Meanwhile, the rapper trails after the model in a white T-shirt, brown suede collared jacket, dark brown trousers, and caramel suede boots.

<span class="photo-credit">Getty Images</span>
Getty Images
new york, new york may 01 kendall jenner and bad bunny are seen heading to a met gala afterparty on may 01, 2023 in new york city photo by gothamgc images
Gotham - Getty Images

April 29, 2023: They go on a dinner date in NYC.

The two are spotted during a night out in NYC, where they eat at celeb hotspot Carbone before heading to Pergola.

For the evening, Jenner wears a transparent brown top with a belted, fur-trimmed micro-miniskirt and boots by Blumarine. Bad Bunny wears a pale-yellow-and-black bomber jacket with a black tee, black trousers, black oval sunglasses, and silver hoop earrings.

April 26, 2023: They’re spotted leaving a concert together.

The pair attend Tyler, the Creator’s concert in L.A. for a casual date night. For the evening, the stars coordinate in white T-shirts and black pants. (Jenner adds a hoodie and baseball cap, and Bad Bunny a pair of dark sunglasses.) They are later photographed leaving the venue in the rapper’s car, where Jenner is seen laughing in the passenger seat.

April 16, 2023: They pack on PDA at Coachella.

The two make a buzzy joint appearance at this year’s music-and-arts festival in Indio, California.

During the artist’s April 14 performance, Jenner supports him from the crowd and is seen dancing to his final song, “Después de la Playa,” alongside a group of friends, per footage captured by fans.

Onstage, the rapper directly alludes to recent dating rumors for the first time in an emphatic speech. “People think they know the lives of famous people—but they don’t,” he says in Spanish. “They don’t know what we feel, what we live through. They will never know what a heart can feel. Don’t believe everything you hear. You won’t get to know the real me through a video on Instagram, an interview, or a TikTok. If you really want to get to know me, I invite you to my home.”

Jenner and Bad Bunny were seen at the festival again on April 15, as they watched Rosalía’s performance with a group of friends. They ended the weekend on April 16, getting cozy in the crowd during one of the Sunday performances.

Later in the evening, Bad Bunny nearly goes Instagram official with the model when he shares a video of himself to his Instagram Story singing along to a song on the radio from a golf cart. Jenner’s voice is heard in the background, and her hair is seen blowing in the wind beside him.

April 4, 2023: Kendall takes Bad Bunny on a horse date.

The model takes things to the next level with Bad Bunny with a romantic horseback riding date at the Hidden Hills Equestrian Center in California.

Photos published by TMZ show the two riding around the corral on one of Jenner’s horses. The rapper later goes on a solo ride while the model smiles and films him.

March 8, 2023: They are captured kissing.

In an outing that confirms their status as an item, the two are photographed sharing a kiss in a parking lot following a night out with friends at a sushi restaurant in West Hollywood.

February 20, 2023: Romance rumors swirl.

Jenner and Bad Bunny first meet through mutual friends when the rapper moves to Los Angeles toward the beginning of February, according to People.

Weeks later, rumors of their fling swirl as the two are captured by TMZ leaving the same restaurant in Beverly Hills, allegedly following a double date with Justin and Hailey Bieber. (The outlet notes that the Biebers headed out of the restaurant almost an hour earlier than Jenner and Bad Bunny, suggesting that the supermodel and rapper spent some alone time.)

Per an anonymous submission to celebrity gossip account DeuxMoi, the two were seen locking lips at a private club earlier in the month, on February 15. “I have witnesses on the scene who saw her in the club,” the source reportedly tells the account. “Word is [Bad Bunny] is in an open relationship.”

On the Monday following the pair’s double date, People reports Jenner and Bad Bunny have indeed been “hanging out.” According to one insider, Jenner “likes” Bad Bunny “and is having fun.” The source adds, “He is different from guys that she dated in the past. He is very charming.”

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