Abel Tesfaye, the man we all know as The Weeknd, has basically built a multi-platinum career out of being the guy you probably shouldn't date. He’s the king of "toxic" R&B. But honestly, while his lyrics paint a picture of late-night regrets and pills in Vegas, his actual dating life has been defined by a few high-profile, long-term relationships that the paparazzi just couldn't get enough of. If you’re wondering who did The Weeknd date, you’re likely looking for more than just a list of names. You want to know how these women influenced the dark, moody tracks that have topped the Billboard charts for a decade.
It’s never just a simple "we're together" with Abel. It's complicated. It's messy. It's usually very, very public despite his attempts to be mysterious.
The Bella Hadid Era: A Timeline of On-Again, Off-Again
Most people start here. Bella Hadid and Abel were the "It Couple" for years. They first sparked rumors back in 2015. They met because he wanted her to be on the artwork for Beauty Behind the Madness. She said no to the art but yes to a date.
Their debut at the 2016 Grammys was iconic. They looked perfect. But behind the scenes, the pressure of two exploding careers started to show cracks. By November 2016, they split for the first time. The reason? Scheduling. It’s the classic Hollywood excuse, but for a world-touring singer and a jet-setting supermodel, it was probably the truth.
Then came the Victoria’s Secret Fashion Show.
You’ve seen the clip. She’s walking the runway in silver lingerie, and he’s performing "Starboy." The eye contact was intense. Fans thought they were back together immediately, but things were actually about to take a sharp turn toward Selena Gomez.
After the Selena detour, Abel and Bella found their way back to each other in 2018. They were spotted kissing at Cannes. They moved in together in New York. For a second, it felt like they might actually make it. They didn't. They broke up again in 2019, and while rumors of a reconciliation pop up every few years, they seem to have finally closed that chapter.
The Selena Gomez "Interlude"
In early 2017, the internet practically melted. Photos surfaced of Abel and Selena Gomez kissing outside a restaurant in Santa Monica. This was a big deal. Not just because they were superstars, but because Selena was part of the "squad" that included Bella’s sister, Gigi Hadid.
They weren't shy. They went to the Met Gala together. They traveled to Italy. Selena even underwent a kidney transplant while they were dating, and reports at the time suggested Abel was a huge support system for her.
But it lasted ten months.
When they broke up in October 2017, Selena was almost immediately spotted back with Justin Bieber. That had to hurt. Abel’s response was the My Dear Melancholy EP. If you listen to "Call Out My Name," it’s pretty clear he’s singing about her. The lyrics mention "I almost cut a piece of myself for your life," which fans widely interpreted as him being willing to donate a kidney to her. Talk about heavy.
The Angelina Jolie Rumors: Fact or Fiction?
This is where things get interesting and a little more speculative. In 2021, the tabloids went wild when Abel was seen leaving dinner with Angelina Jolie. Multiple times.
Now, on paper, this feels like a fever dream. The R&B star and the Oscar-winning UN ambassador? But they were seen at Giorgio Baldi in Santa Monica—his favorite spot—multiple times. Neither ever confirmed a romance.
Some insiders claimed it was strictly business. Abel was moving into acting and producing with The Idol, and who better to learn from than Jolie? Others pointed to his song "Here We Go... Again," where he sings about his "new girl" being a "movie star."
"My new girl, she a movie star / I loved her right, make her scream like Neve Campbell."
The Neve Campbell line is a Scream reference, obviously, but the "movie star" label stuck to Jolie in the press. Whether they were actually a couple or just bonded over film projects remains one of the more mysterious entries in the "who did The Weeknd date" saga.
Simi Khadra and the Current Vibe
Lately, Abel has been linked to Simi Khadra. She’s one half of the DJ duo Simi Haze and, in another twist of Hollywood irony, was once considered a friend of Bella Hadid.
They were first caught on camera kissing at his 32nd birthday party in 2022. Since then, they’ve been spotted at Coachella, traveling through Europe, and just generally being low-key. Compared to the high-drama years of Bella and Selena, this relationship seems much more grounded. They aren't doing the big red carpet reveals. They aren't posting gushing Instagram captions.
It feels like he’s learned his lesson about the spotlight. Or maybe he’s just tired. Either way, Simi seems to be the one currently in his orbit as he transitions from "The Weeknd" persona back into Abel Tesfaye.
Why Does This Matter for the Music?
You can't separate Abel’s dating life from his discography. It’s impossible.
- Beauty Behind the Madness: Mostly about the lifestyle, but the early Bella influence is there.
- Starboy: The peak of his public fame and his first real "celebrity" relationship struggles.
- My Dear Melancholy: The Selena breakup album. Raw, bitter, and sad.
- After Hours: A mix of longing for Bella and the loneliness of being the biggest star in the world.
- Dawn FM: A more reflective, existential look at love.
The women he dates aren't just partners; they are muses. When he sings about "the city's cold and empty," he’s usually talking about the space they left behind.
The Complicated Reality of Fame
Dating Abel Tesfaye seems exhausting. He’s admitted in interviews—like with Rolling Stone—that he’s a workaholic. He’s often in the studio until 4 AM. He lives in a world of high-concept art and "the character" he’s created.
There were also rumors about him and Rosalia after their "La Fama" collaboration, but those were mostly just fan theories fueled by their incredible chemistry in the music video. Same goes for the brief chatter about him and Yovanna Ventura back in 2017.
The truth is, for a guy who sings about being "heartless," he seems to fall pretty hard. His relationships last years, not weeks.
Actionable Takeaways for Fans and Collectors
If you're following Abel's journey, his dating history offers a roadmap to his music. To truly understand the "Abel" era moving forward, keep these points in mind:
- Listen to the lyrics geographically. He often mentions specific places (like "The 6" or New York vs. LA) to signal which relationship he’s referencing.
- Watch the credits. Simi Khadra and others in his circle often appear in the creative periphery of his projects.
- Check the "Starboy" archives. Many of the unreleased tracks from that 2016-2017 era give more insight into his headspace during the transition from Bella to Selena.
- Follow the aesthetic. Abel changes his look with his relationships and his albums. The "After Hours" red suit was a specific persona that coincided with his single era.
Understanding the history of who The Weeknd dated isn't just about gossip. It’s about understanding the emotional catalyst for some of the most influential music of the 21st century. As he sheds the "Weeknd" name, expect his future relationships to stay even further under the radar. He’s looking for something real now, away from the flashing lights of the Victoria's Secret runway.