From their first road trip to a courtside kiss, here’s a breakdown of Kendall Jenner and Devin Booker’s low-key love

While most of the Kardashian-Jenner family are used to having their relationships play out in the public eye, Kendall Jenner has always preferred to take a more laid-back approach to her love life.

The supermodel was first linked to NBA All-Star and Phoenix Suns guard Devin Booker in April 2020, but only confirmed the rumored romance on Valentine’s Day 2021.

In a 2019 interview with Vogue Australia, Jenner revealed that her reluctance to reveal too much about her relationships comes from watching her older sisters navigate the highs and lows of dating in the spotlight.

“A relationship is only meant to be between two people, and the second you make it the world’s business is when it starts messing with the two people mentally,” she said. “Like once everyone is let in, you’re letting all these opinions into your relationships, and I don’t think that’s fair.”

KENDALL JENNER INSTAGRAM

Throughout their romance, the private pair offered a few glimpses into their love story, from their first quarantine road trip to their sweet Instagram tributes. However, in November 2022, news broke that Jenner and Booker had called it quits a month prior due to their demanding work schedules.

Here’s everything to know about Kendall Jenner and Devin Booker’s relationship.

April 2020: Kendall Jenner and Devin Booker go on a road trip to Sedona, Arizona

Jenner and Booker first sparked romance rumors when they were spotted at a rest stop during a quarantine road trip to Sedona, Arizona. At the time, a source told PEOPLE that the pair weren’t dating — at least not yet.

“She and Devin have a lot of mutual friends. They’re just friends for now but you never know with Kendall,” the source said.

After the hangout garnered criticism on social media, with Twitter users accusing Jenner of dating a lot of basketball players, the social media star shot back with a fiery tweet of her own.

“They act like i’m not in full control of where i throw this cooch,” she wrote.

August 2020: Kendall Jenner and Devin Booker head to dinner with her sister Kylie

It was a family affair as Jenner’s younger sister Kylie stepped out for dinner with Jenner and Booker. The trio dined together at Nobu restaurant in Malibu, California, days after the Phoenix Suns shooting guard sent fans into a frenzy with a flirty exchange on Jenner’s Instagram account.

“I like strawberries,” Booker wrote under Jenner’s glam post captioned with a strawberry emoji. The model responded with four more strawberry emojis.

September 2020: Kendall Jenner and Devin Booker enjoy lake life with Justin and Hailey Bieber

KENDALL JENNER/INSTAGRAM

Booker joined Jenner and her longtime friends Justin and Hailey Bieber for a lake vacation in Idaho in September 2020. The group spent several days at the Gozzer Ranch Golf & Lake Club, where they relaxed by the lake and hung out around a campfire.

“Kendall seems very happy,” an insider told PEOPLE at the time. “Devin is very sweet to her. He spends a lot of time with Kendall’s family and friends too. They seem to be on the same page. They haven’t been working lately and have been able to enjoy quiet beach outings and dinners instead. They both seem to enjoy the quiet time together.”

October 2020: Kendall Jenner and Devin Booker make an appearance at Kim Kardashian’s birthday party

Eagle-eyed internet sleuths spotted the couple in the background of a photo from Kim Kardashian’s birthday trip. The controversial 40th birthday bash was held on a private island in Tahiti and attended by family and close friends of the reality star. As photos from the event started to surface, fans quickly pointed out Jenner and Booker standing next to each other in Scott Disick’s Instagram post.

Jenner also posted a few solo photos from the vacation, including a couple of bikini shots and snaps of the picturesque landscape. An insider told PEOPLE that the model “is very private about their relationship,” but added it’s “obvious that they have something special going on.”

November 2020: Kendall Jenner cuddles with Devin Booker at her birthday party

To celebrate her 25th birthday, Jenner threw a star-studded party at Harriet’s Rooftop above 1 Hotel in West Hollywood, California. The event also doubled as a Halloween party, and the model donned a skin-tight bodysuit and blonde wig to transform into Pamela Anderson circa Barb Wire.

The reality star later shared a series of snaps from the party’s photo booth, one of which showed her cozying up to Booker.

January 2021: Devin Booker posts a sexy snap of Kendall Jenner on his Instagram story

In January 2021, Booker turned up the heat on the couple’s romance by reposting a steamy picture Jenner shared of herself clad in a blinged-out bikini and lounging by the pool.

“Whew,” the NBA player captioned the cheeky pic along with a panting emoji.

February 2021: Kendall Jenner and Devin Booker go Instagram official

Jenner and Booker celebrated Valentine’s Day 2021 by making their relationship Instagram official. The supermodel shared a lighthearted moment between the couple as they lay intertwined on a countertop captioned with a heart emoji. Booker posted a video of the two sprawled on a blanket while snuggling with a dog as they enjoyed some time outdoors. The athlete added a single orange heart emoji to the black and white post.

“What first seemed like a fun hookup is now a relationship,” a source told PEOPLE. “They are exclusive and Kendall is very happy with Devin.”

June 2021: Kendall Jenner and Devin Booker celebrate their first anniversary

Kendall Jenner and Devin Booker. KENDALL JENNER/INSTAGRAM

The pair gave a rare glimpse into their relationship as they celebrated their first anniversary. Jenner and Booker both commemorated the occasion with social media posts. The Keeping Up with the Kardashians star shared a couple of PDA-filled snaps on Instagram, which showed her embracing Booker from behind and another wrapped in each other’s arms.

Booker tagged the model in a photo of a dining set-up at sunset, simply captioned “1.” He also added a snap of a solo Jenner and another of the couple titled “365” and “52”; all references to their one-year milestone.

“She is crazy about him. She has never looked happier. Her whole family loves Devin too,” a source told PEOPLE.

“Devin is such a cool guy,” the insider added. “He is very low-key and doesn’t want to be a celebrity. He is very sweet to Kendall.”

July 2021: Kendall Jenner supports Devin Booker at the NBA Finals

KEVORK DJANSEZIAN/GETTY

In July 2021, Booker helped lead his Phoenix Suns squad to the NBA Finals for the first time since 1993, and Jenner was at Game 1 to cheer on her man.

“I’m not emotional, you are,” she captioned a photo of the pregame festivities in her Instagram stories.

August 2021: Kendall Jenner and Devin Booker go an Italian getaway

Devin Booker, Kendall Jenner. KENDALL JENNER/INSTAGRAM

After a busy summer, which saw Booker win gold at the Tokyo Olympics as part of the U.S. Men’s Basketball team and Jenner promoting her tequila brand, the couple jetted off to Italy for some downtime. During their Amalfi Coast getaway, the twosome made multiple stops, which included a night out in Capri, a yacht excursion, and a stroll along the region’s cobblestone streets at sunset.

September 2021: Kendall Jenner opens up about Devin Booker on The Tonight Show

Jenner typically keeps her relationships private, but during an appearance on The Tonight Show, she revealed to host Jimmy Fallon that Booker has been bonding with her younger family members — especially one of her nieces.

“He loves them,” Jenner said, adding that he and Kylie’s daughter Stormi are particularly close. “Him and Stormi have an amazing relationship. She has the biggest crush on him, and I’m, like, jealous sometimes. I’m like, ‘Stop. Can you guys not?’ ”

October 2021: Devin Booker teases Kendall Jenner about her pumpkin carving skills on Twitter

Jenner and Booker put their pumpkin carving skills on display in October 2021 as the duo geared up for Halloween. However, the NBA star wasn’t too impressed with his girlfriend’s technical approach to the process.

“Pumpkin dont count if you used a stencil,” he tweeted. Jenner retweeted the jab, responding, “I feel personally attacked.”

A week later, on October 25, Jenner shared a courtside kiss with Booker after his Phoenix Suns defeated the Los Angeles Lakers.

November 2021: Devin Booker posts a sweet birthday tribute to Kendall Jenner

DEVIN BOOKER/INSTAGRAM

Jenner turned 26 in early November 2021, and to mark the occasion, Booker took to Instagram to gush over his girlfriend. The NBA player posted a series of photos to his Instagram story, including one featuring Jenner gazing into the distance with a smiling Booker in the background, captioned, “Most beautiful woman.”

A few days earlier, the reality star called Booker her “best friend” as she honored his 25th birthday with a couple of Instagram story snaps and a trio of heart emojis.

December 2021: Kris Jenner includes Devin Booker in a family tradition

The Kardashian-Jenner crew is known for their elaborate holiday festivities, sparing no expense or detail. One of those traditions includes a personalized gingerbread house that the family matriarch, Kris Jenner, gifts her six children every year. And in 2021, Booker was welcomed into the fold. Kris added the NBA star’s name to Jenner’s custom confection along with the names of her daughter’s three dogs.

January 2022: Kendall Jenner and Devin Booker kick off the New Year with a cozy weekend away

Jenner and Booker rang in the New Year together in January 2022 with a weekend holiday. The model shared a carousel of photos on Instagram showing her and Booker in what appeared to be a mountaintop escape, complete with wooden panels and a roaring fireplace. In one mirror selfie, the couple cuddled together in warm clothing while Booker enjoyed a glass of wine.

A few days later, Jenner took to social media to drum up support for Booker’s NBA All-Star Game campaign. “Y’all know I wanna see #DevinBooker play in the All-Star Game #NBAAllStar,” the Keeping Up With the Kardashians alum tweeted.

February 2022: Kendall Jenner and Devin Booker spend time with the Biebers at the Super Bowl

Justin Bieber, Hailey Bieber, Kendall Jenner and Devin Booker. KEVIN MAZUR/GETTY

Jenner and Booker made a rare public appearance as a couple at the 2022 Super Bowl in L.A. Frequent double date partners Hailey and Justin Bieber joined the two at SoFi Stadium to watch the Los Angeles Rams take on the Cincinnati Bengals. The group even color-coordinated in white tops.

March 2022: Devin Booker talks about public life with his girlfriend Kendall Jenner in an interview

In an interview with the Wall Street Journal, Booker was asked whether his life in the spotlight as an athlete and as Jenner’s boyfriend is hard.

“I wouldn’t say hard,” the NBA star responded. “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.”

He added, “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.”

May 2022: Kendall Jenner and Devin Booker attend Kourtney Kardashian and Travis Barker’s wedding

Jenner brought Booker along as her date to sister Kardashian’s wedding to Blink-182 musician Travis Barker in Italy. The two were spotted holding hands as made their way to Ristorante Puny in Portofino, where the Kardashians, Barkers, and other loved ones dined ahead of the couple’s wedding on May 22.

June 2022: Kendall Jenner and Devin Booker reportedly break up

After two years together, Jenner and Booker reportedly called it quits in June 2022, according to Entertainment Tonight and E! News.

“Kendall feels like they’re on different paths,” a source told ET. Another insider told the outlet that Jenner and Booker “have had discussions about their future but they are not on the same page.”

Another source also told E! News that the pair “hit a rough patch recently and have been split for about a week and a half.”

June 26, 2022: Kendall Jenner and Devin Booker spotted together after reportedly breaking up

Jenner was spotted with Booker over the weekend at Soho House in Malibu following their alleged breakup earlier in June. The two were captured by paparazzi and appeared to be in good spirits, as they were photographed smiling and sharing a laugh together.

July 20, 2022: Kendall Jenner reportedly attends wedding with Devin Booker

KENDALL JENNER/INSTAGRAM

Since being spotted at Malibu’s Soho House in June following their alleged breakup, Jenner and Booker have yet to confirm their relationship status — but about one month later in July, the 818 Tequila founder posted a snap with a mystery man causing fans to spectate.

While attending a friend’s wedding over the weekend, Jenner shared a photograph of herself and a guest on her Instagram Story. Although the guest’s head was cut off in the picture, speculators think it’s Booker — especially since a video was uploaded by fan account @kendallsjbr showing Jenner and Booker walking together inside the wedding venue.

July 31, 2022: Kendall Jenner and Devin Booker enjoy an adventurous day together

Amidst reconciliation rumors, the former couple met up for some outdoor activities. Jenner shared a video of Booker throwing an axe in a wooded area on her Instagram Story, which Booker reposted with a bullseye emoji.

The model also posted a video of herself ziplining, as well as a photo of a suspension bridge and a shot of her feet high above the foliage below.

August 27, 2022: Kendall Jenner and Devin Booker step out for a date night in L.A.

Jenner, who was all smiles, clung to Booker as they left Catch Steak in West Hollywood, California. The reality star was dressed in a plunging crop top, black leather pants and pink heels. Booker looked casual in a graphic tee, jeans and baby blue Converse.

September 7, 2022: Kendall Jenner and Devin Booker attend NBA event in L.A.

Jenner and Booker seem to be putting rumors of a breakup to bed. The couple were spotted together in L.A. at the release party for NBA 2K23 in early September 2022.

While Booker walked the red carpet alone, a source told PEOPLE that the couple shared some time together among the crowd.

September 11, 2022: Kendall Jenner and Devin Booker spend a weekend in N.Y.C

Later that month, the duo were seen smiling, cheering and kissing while attending the US Open in N.Y.C.

The on-again couple were also spotted at the SS23 Marni fashion show that weekend, apparently making the most of their trip to the Big Apple.

October 19, 2022: Devin Booker comments about Kendall Jenner on Kim Kardashian’s post

Kardashian posted a photo of the whole family to promote new episodes of The Kardashians on Hulu.

“Middle,” Booker wrote in the comments, referencing his girlfriend who appeared front and center in the photo. Jenner liked the comment but didn’t reply.

November 21, 2022: PEOPLE confirms that Kendall Jenner and Devin Booker have quietly split

On Nov. 21, 2022, several sources confirmed to PEOPLE that Jenner and Booker had ended their relationship a month prior due to their busy careers.

“Both have incredibly busy schedules right now with their careers and they’ve decided to make that a priority,” a source told PEOPLE.

“They have a lot of love and respect for each other and wish only the best,” a second insider added.

March 17, 2023: Bad Bunny disses Devin Booker in new song

Bad Bunny is Kendall Jenner’s rumored new beau. Roughly a month after the couple were first spotted together, the singer seemingly dissed Booker in his new track “Coco Chanel.”

Bad Bunny rapped that the “sun in Puerto Rico is hotter than in Phoenix” and “she knows it.” In a now-deleted Instagram comment, the Phoenix Suns player responded: “He worried about another MAN again.”