Kendall Jenner and Bad Bunny: A Complete Relationship Timeline

Kendall Jenner and Bad Bunny began dominated the tabloids for a little under a year before seemingly calling it quits. Now, it looks like they may be back together, if a bit more low-key about it.

The rumors that started it all first surfaced around Valentine’s Day 2023. In just one week, the model and Grammy-winning rapper allegedly made out at a private club in Los Angeles and went on a double date with Justin and Hailey Bieber, two of Jenner’s besties.

Jenner ended her relationship with NBA player Devin Booker in the fall of 2022 and seemed to be ready to mingle. Meanwhile, Bad Bunny was previously linked to singer and jewelry designer Gabriela Berlingeri since 2017, but the pair reportedly called it quits sometime in 2023.

Alas, after nine months of public make outs and courtside photos, it looked like Bad Jenner was over before the new year…until those reconciliation rumors began circulating this January. And while those were muddled by conflicting reports that Jenner was rekindling her romance with Booker, a Met Gala moment between the Kendall Jenner and Bad Bunny signaled that their story might not be over.

So, what’s really going on? Here is a detailed timeline of all the events, rumors, and anon sources so far.

February 2023: Someone sends a blind item to the celeb gossip account DeuxMoi suggesting that a person of Jenner’s description and Bad Bunny were making out at a private club in Los Angeles.

“This single, famous model sister was seen playing tonsil hockey with Bad Bunny at a private L.A. club last night,” the celebrity gossip account posts on February 16. The anon gossip whisperer later confirmed it was Jenner on her Deux U podcast: “So I’m revealing it was Kendall Jenner and Bad Bunny, I have witnesses on the scene who saw her in the club,” the host said.

February 18, 2023: Jenner and Bad Bunny are spotted leaving the same restaurant through separate exits. According to a TMZ report, the model and rapper were on a double date with Justin and Hailey Bieber at Wally’s in Beverly Hills.

February 20, 2023: A source tells People that Kendall and Bad Bunny “are spending time together.”

Another source told the outlet, “Kendall recently started hanging out with him. They were introduced by friends. He moved to LA a few weeks ago and bought a house. She likes him and is having fun,” they said. “He is different from guys that she dated in the past. He is very charming.”

March 8, 2023: Jenner and Bad Bunny are photographed embracing after they left LA hotspot Sushi Park on Tuesday, March 7.

In photos obtained by TMZ, the pair appear to keep their distance as they walk out of the restaurant. However, as Jenner stands outside her car, they share a hug and a kiss. Per the outlet, the couple dined with a group, including Jenner’s sister Kylie.

Meeting the family already? Sounds like things could be getting serious….

March 29, 2023: A source tells Us Weekly that Jenner and Bad Bunner were “being very affectionate” and “openly kissing” at Sushi Fumi in LA.

April 15, 2023: Jenner is captured on camera dancing during Bad Bunny’s Coachella set. The model wore a denim miniskirt and black bomber jacket to her rumored boyfriend’s performance.

April 16, 2023: The pair are photographed getting “very cozy” at the music festival.

April 29, 2023: Jenner and Bad Bunny are spotted on their way to dinner at New York City celebrity hotspot Carbone and later photographed leaving the restaurant in the same car.

May 1, 2023: They’re “getting more serious,” a source tells People. “It was a slow start, but they spend almost every day together now,” the source says. “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.”

May 12, 2023: The pair share some PDA moments while sitting courtside at a Lakers game. Note Bad Bunny’s hand placement as well as their coordinated snakeskin boots….

Kendall Jenner and Bad Bunny attend the Western Conference Semifinal Playoff game between the Los Angeles Lakers and Golden State Warriors at Crypto.com Arena on May 12, 2023.

Kevork Djansezian/Getty Images

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 Crypto.com Arena on May 12, 2023 in Los Angeles, California. (Photo by Kevork Djansezian/Getty Images)Kevork Djansezian/Getty Images

June 21, 2023: Bad Bunny is trying to protect his privacy in the wake of all this speculation. “I know something is going to come out. I know [people are] going to say something,” Bad Bunny told Rolling Stone for his July/August cover interview, per People. “People know everything about me, so what’s left for me to protect? My private life, my personal life.” When asked to comment on the recent rumors, he doubled down: “That’s the only answer. In the end, the only thing I have is my privacy.”

The rapper went on to decry the new era of social media, where “everyone’s a paparazzi,” saying, “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. There could be someone in line with, I don’t know, weird pants on or something, and someone is there filming them.”

He continued, “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.”

August 13, 2023: Jenner and Bad Bunny are caught canoodling at Drake’s tour stop in Inglewood, California. An eyewitness told Page Six the model and rapper were “making out while Kim [Kardashian] was right next to them” in the VIP section. In clips captured by fans and subsequently shared to TikTok, the pair can be seen whispering in each other’s ears and holding one another close as “God’s Plan” plays in the background.

August 27, 2023: Bad Bunny seems to soft-launch his relationship with Jenner on Instagram Stories. In one video from a hike, the rapper can be heard talking with someone who sounds a lot like Jenner, warning her, “Mami, be careful.”

“Rabies?” his hiking partner asks, before he clarifies: “The mosquitoes.”

September 12, 2023: In his cover interview with Vanity Fair, Bad Bunny declines to comment about whether or not his relationship with jewelry designer Gabriela Berlingeri at all overlapped with his relationship with Jenner.

As you’ll recall, “Bad Jenner” was first reported by Deux Moi back in February 2023. Per Vanity Fair, the celebrity gossip account had not reported a breakup between the rapper and Berlingeri, which led them to speculate that perhaps the two were in an open relationship. By way of response, writer Michelle Ruiz reports, Bad Bunny “laughs heartily” before his publicist “shuts down any comment.”

True to form, Bad Bunny did not discuss his relationship with Jenner in any meaningful way but did bemoan the paparazzi.

September 16, 2023: Kendall Jenner rocks a very un–Kendall Jenner ’fit to dinner with Bad Bunny. In a photo published by People, she can be seen exiting NYC’s Cosme in an oversized knit sweater with colorful floral details, paired with a camel-colored weekend bag, straight-leg black jeans, and loafers. Meanwhile, Bad Bunny wore a pair of light-wash baggy jeans and a white button-down, and had a blue tote of his own. You can see the image here.

September 30, 2023: Kendall Jenner and Bad Bunny go Instagram official…on Gucci’s grid. The pair starred in a romantic ad campaign for Gucci Valigeria luggage. See the adorable pics (and video) here and here and here.

October 29, 2023: TMZ shares photos of Jenner and Bad Bunny having breakfast the day after hosting a big Halloween party.

November 14, 2023: Jenner sparks breakup rumors with a cryptic Instagram post. “What’s meant for me, will simply find me,” she captioned an image of a sunset.

“Sounds like a break up post,” one of many fans replied.

December 15, 2023: Kendall Jenner is photographed in Aspen without Bad Bunny. As Page Six notes, the pair were last photographed together on October 29.

December 17, 2023: A source tells People that Bad Bunny and Kendall Jenner have split.

January 3, 2024: Jenner tells her followers to “go love on the people you hold close to your heart, and don’t waste a second ❤️” in a reflective Instagram post, adding, “2024, shower me with love and laughter, gratitude and growth, patience and presence.”

January 4, 2024: A source tells People that the pair “celebrated New Year together with friends near Barbados.” However, the same insider claimed they were “not on the same flight,” and are not “back together.”

February 23, 2024: Plot twist! Jenner and Devin Booker may be giving it another go. After Booker was spotted in the Kardashian’s Super Bowl suite earlier this month, sources told TMZ that the former couple “have been spending more time together lately,” but are “not rushing into things.”

Sources also claim to have spotted Jenner in Dallas around the same time Booker was in town for the Phoenix Suns game against the Dallas Mavericks…Interesting!

May 5, 2024: Not so fast! Bad Bunny and Kendall Jenner are spotted cozying up together at a Met Gala after party. In one photo from the event, the pair are seated very close together on a sofa, despite there seeming to be plenty of room to spread out…and don’t get us started on the way Bad Bunny is looking at the model!

“They were sitting together, laughing and having the best time,” a source tells People. “They were very much enjoying each other’s company. Sitting close and whispering in each other’s ears.”

WWD/Getty Images

May 17, 2024: “Kendall and Bad Bunny are still in contact and spend time together when they can,” a source tells Entertainment Tonight. “There’s a strong connection between them whenever they’re together and they have the same chemistry that they’ve always had.”

May 18, 2024: Jenner is spotted dancing at one of Bad Bunny’s concerts in Orlando, Florida. It seems the model was attempting to fly under the radar in a brown hoodie, but was unsuccessful.

May 24, 2024: Jenner and Bad Bunny appear to enjoy a “private dinner” in Miami, based on photos and video published by TMZ. Sources tell the publication that the duo were seated in a VIP room at Gekko Japanese Steakhouse following the rapper’s concert at the Kaseya Center.

This post may be updated.