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The Weeknd Dating History: From Simi Khadra to Angelina Jolie

Abel Tesfaye, professionally known as The Weeknd, has been known to make headlines for his chart-topping tracks and public relationships.

Throughout his decade-long career, The Weeknd has had two significant relationships with model Bella Hadid and actress Selena Gomez.

The 32-year-old was also linked to actress Angelina Jolie and DJ Simi Khadra.

So, who is The Weeknd dating now? Let’s take a deep dive into The Weeknd’s dating history.

Who Is The Weeknd Dating Now?

The Weeknd Dating History: From Simi Khadra to Angelina Jolie
Simi Khadra and The Weeknd were spotted making out in February 2022 while celebrating the singer’s 32nd birthday in Las Vegas, Nevada.

Although it is unclear who The Weeknd is currently dating, his last alleged romance was with Simi Khadra.

Khadra and The Weeknd were spotted making out in February 2022 while celebrating the singer’s 32nd birthday in Las Vegas, Nevada.

The Weeknd Dating Timeline

TAMPA, FLORIDA – FEBRUARY 04: The Weeknd speaks during the Pepsi Super Bowl LV Halftime Show Press Conference at Tampa Convention Center on February 04, 2021 in Tampa, Florida. (Photo by Kevin Mazur/Getty Images for TW)

The Weeknd’s love life with his ex-girlfriends Bella Hadid, Selena Gomez, and rumored flings Angelina Jolie and Simi Khadra share common similarities.

The list included The Weeknd dining at what appears to be his favorite Italian restaurant and showcasing his raw emotions about some of the women in songs.

The Weeknd and Bella Hadid (2015-2019)

Bella Hadid
Bella Hadid and The Weekend were spotted leaving Kylie Jenner’s birthday bash late Thursday night. (Image courtesy of Elle)

The Weeknd began dating supermodel Bella Hadid in 2015 after the singer asked her to pose for the cover of his 2015 album “Beauty Behind the Madness.” Although Hadid denied the offer, the pair did, however, remain in touch.

According to Us Weekly, Hadid and The Weeknd’s friendship blossomed into a relationship in May that same year. In December 2015, the pair would officially collaborate together after Hadid appeared in The Weeknd’s “In The Night” music video.

All appeared to be going well with the couple until November 2016.

The History of The Weeknd and Bella Hadid’s On-Again, Off-Again Relationship

Bella Hadid and The Weeknd reportedly broke up because of their busy schedules. 

In November 2016, news outlets reported that Hadid and The Weeknd broke up because of their busy schedules. 

A source told People Magazine, “Their schedules have been too hard to coordinate, and he is focusing on finishing and promoting his album. They still have a great deal of love for one another and will remain friends.”

Their split would be short-lived because after The Weeknd’s relationship with Selena Gomez ended in October 2017, seven months later, in May 2018, he and Hadid were spotted kissing at the Cannes Film Festival

Hadid and The Weeknd would remain together until August 2019, when they called it quits a second time. Since then, it’s been reported that the pair are “in touch” again.

The Weeknd and Selena Gomez (2017)

The Weeknd, left, and Selena Gomez attend The Metropolitan Museum of Art’s Costume Institute benefit gala celebrating the opening of the Rei Kawakubo/Comme des Garçons: Art of the In-Between exhibition on Monday, May 1, 2017, in New York. (Photo by Evan Agostini/Invision/AP)

The Weeknd dated Selena Gomez for about nine months in 2017. Gomez and The Weeknd first met in 2015 at Victoria’s Secret Fashion Show, where they both performed. 

Years later, in January 2017, The Weeknd would be romantically linked to Gomez after the stars were spotted kissing following a dinner at Giorgio Baldi in Santa Monica, California. This incident occurred on Jan. 10, 2017, months after The Weeknd and his ex, model Bella Hadid, first break up.

At the time, a source told People magazine that although bystanders saw Gomez and The Weeknd sharing a meal, laughing, holding hands, and kissing, the relationship was “new and nothing serious.”

Months following those claims, the couple ultimately paraded their love by sharing various posts on their respective social media accounts and taking lavish trips to Italy and The Weeknd’s hometown of the Canadian capital, Toronto. 

Things continued to heat up between Gomez and The Weeknd that May when they made their red carpet debut as a couple at the Met Gala. The pair appeared to be doing well even after Gomez had to undergo a kidney transplant for her ongoing lupus battle. 

It was reported that The Weeknd even prioritized spending more time with Gomez by scheduling his tour around her surgery timeline. Despite his efforts, Gomez and The Weeknd would split on Oct. 30. 

People magazine reported that Gomez and The Weeknd’s breakup stemmed from their long-distance relationship and that they have been contemplating this for months. 

Another insider denied that the actress’ ex Justin Bieber contributed to the pair’s demise, even though they were spotted hanging out numerous times following the announcement. At the same time, The Weeknd was seen spending time with Bieber’s ex, model Yovanna Ventura.

The Weeknd would allegedly reference his breakup with Gomez in the 2018 song “Call Out My Name”

The Weeknd and Angelina Jolie (2021-2022)

The Weeknd was inspired by French Montana to donate fund a Ugandan health center. (Andrew Chin/Getty Images)

The Weeknd and Angelina Jolie made headlines in July 2021 after the pair were spotted having dinner at Giorgio Baldi in Santa Monica, California. The pair allegedly met through mutual friends in the music and film industry. 

According to The Sun, Jolie and The Weeknd spent hours dining at the Italian restaurant and left separately to “avoid raising suspicion.” A few months later, in September, The Weeknd was spotted having dinner with Jolie again at the same restaurant. 

As dating rumors began circulating online, an insider told E News! that the duo weren’t dating but were discussing new creative ventures over their similar interests in the arts and humanitarian work. 

The source said, “They are not dating. They have mutual interests and are enjoying putting their ideas together to see what they can come up with. They have been recently talking about partnering on a few humanitarian projects together. He loves talking about movies and the art form.”

Despite insiders denying the dating rumors, it appears things may have taken a turn romantically for Jolie and the singer and on Jan. 7, 2022, after The Weeknd released his “Dawn FM” album. 

In the song titled “Here We Go…Again,” The Weeknd allegedly references his romance with Jolie. He said in the track, “My new girl, she a movie star. I loved her right, make her scream like Neve Campbell.”

Although The Weeknd and Jolie didn’t publicly discuss their alleged relationship, the dating rumors simmered down in February after the Canadian singer was seen hanging out with Simi Khadra. 

The Weeknd and Simi Khadra (2022)

The Weeknd and Simi Khadra were romantically linked in early February 2022 after the pair were reportedly caught having dinner in Los Angeles. Khadra is a professional DJ alongside her twin sister Haze Khadra, and they make up the duo act called “Simi Haze”

At the time, an insider told E News! that The Weeknd and Khadra’s relationship was strictly platonic. That person said, “The Weeknd and Simi are not dating. They’ve been friends for years.”

A few weeks later, on Feb. 22, The Weeknd and Khadra were spotted kissing in Las Vegas, Nevada. According to TMZ, the incident occurred around 2 a.m. at the “Party Monster” singer’s birthday party at a club named Delilah. The Weeknd turned 32 on Feb. 16.

Since then, no additional details about The Weeknd and Khadra’s relationship have been released to the public, so it’s safe to say that their romance may have been short-lived.

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