Britney Spears’ boyfriend just may be the biggest #FreeBritney supporter in the world. Spears has been dating Sam Asghari, a 27-year-old Iranian-American actor and model, for nearly five years — and their relationship timeline proves that not only is he in it for the long haul, but he’s also right by Spears’ side as she fights to end her controversial conservatorship.
Like a classic pop star fairytale, Spears met Asghari on the set of her “Slumber Party” music video in 2016, where he played the sexy love interest who immediately becomes intrigued by the star. While they proudly show each other off in workout videos and candid photos shared on Instagram, Asghari has been relatively quiet about their relationship in the press, even in the face of rumors about Spears’ personal life and legal battle. Now that she’s actively advocating for the end of her conservatorship, Asghari has been her No. 1 ally, and their relationship timeline shows that he’s been there throughout all of the hardships for almost half a decade now.
October 2016: “Slumber Party”
Spears met Asghari while filming the music video for her Glory single “Slumber Party” featuring Tinashe in October 2016. When she’s not frolicking around a lavish mansion with her collaborator Tinashe in the video, which premiered in November that year, Spears seduces Asghari into having a little slumber party, even crawling up a lavish dining table and licking milk straight out of Asghari’s bowl. Anyone would’ve instantly fell in love with Spears in that moment.
January 2017: Instagram Official
Rumors that Spears and Asghari had become an item started surfacing at the end of 2016 because of the “Slumber Party” video. However, she made their relationship Instagram official on New Year’s Day, sharing a photo of the couple at dinner with Asghari’s arm wrapped around her and wishing fans a simple “Happy New Year.”
Later that month in a radio interview, Spears opened up about how she connected with Asghari, saying they naturally bonded while waiting to film scenes for the video. “We were sitting there and we were waiting together for 20 minutes at a time,” she explained. “So we were basically forced to talk to each other and he has no idea — I mean, he knows my name — but he doesn’t know me as a person. He’s like, ‘What is this girl like?’ and I have no idea who the hell he is.” After filming the video, Spears said she made the first move and invited him out for sushi. “I found his number in my bag,” she explained. “I was like, ‘He is really cute, this guy is really cute.’ So I called him and ever since then, he is just a really fun, funny person.”
February 2017: Their Public Appearance
On Feb 12, 2017, Spears and Asghari made their first public appearance together at Clive Davis’ annual Pre-Grammy Gala. While Asghari didn’t walk the red carpet with her, it still marked their debut as a couple. Since then, they have also attended the GLAAD Media Awards in 2018 and the Once Upon a Time ... in Hollywood red carpet premiere in 2019 together, among other events.
September 2017: Disneyland
As any couple knows, no love story can ever be complete until you go to Disneyland together. Spears and Asghari hit up the Happiest Place on Earth on Sept. 10, 2017. Not only was it their first time at the theme park together, but Asghari was there to celebrate the birthdays of Spears’ sons — Sean Preston and Jayden James Federline — demonstrating how far they had come in their relationship.
February 2018: Their First Anniversary
In February 2018, Spears belatedly celebrated their first anniversary as a couple on Instagram, sharing a photo of them posing near a scenic waterfall. “I’ve been with this man for over a year,” she wrote. “Everyday he inspires me to be a better person and that makes me feel like the luckiest girl in the world!”
July 2018: Sam’s Pickup Line
Nearly two years after they started dating, Asghari told his story of how they connected in an interview with Men’s Health, revealing that he was nervous to meet the superstar. “I was excited that I get to meet one of the biggest artists of all time,” he said. “I had butterflies.” However, his attempt to “Break the Ice” almost completely backfired. “She said, ‘Hi, I’m Britney,’ and I said, ‘I’m sorry. What’s your name again?’” he recalled. “I tried to be funny. I don’t think anybody got it.” Evidently, Spears was the only one who did, and the down-to-Earth joke led to them talking during breaks and eventually sharing phone numbers before the video shoot wrapped.
April 2019: Sam’s Support
After it was reported that Spears entered a mental health facility in April 2019, Asghari took to Instagram to publicly support her. “It isn’t weakness, It’s a sign of absolute strength, people should only be inspired by this, at least I am,” Asghari captioned his post, completing it with #stronger, after Spears’ 2000 hit self-empowerment anthem.
May 2019: Still Going Strong
On May 17, 2019, Spears posted a slideshow of three selfies with her and Asghari on Instagram, with the simple caption, “I love this man.” Even in the face of adversity (Spears later revealed that she was allegedly held at the mental health facility against her will), Asghari had proven to be a safe haven for her.
March 2020: Sam’s Birthday
On March 4, 2020, Spears commemorated her boyfriend’s birthday by posting a seductive photo of Asghari in the bathtub and revealing that she took the picture, saying that he was “the only man I’ve ever photographed in my life” on Instagram. “Yes folks, he’s a stunner,” she captioned the post. “But I must say this shot is my favorite on his page …… why you ask ????! Well it’s because I shot it of course !!!! All I said was don’t look at the camera ….. he listened and it was magic !!!!... Happy Belated B-day @samasghari ..... love you !!!!!”
February 2021: “Jamie is a total d*ck”
After the premiere of Hulu’s New York Times documentary Framing Britney Spears, Asghari made a rare statement about Spears’ family on his Instagram Story and spoke out against her father and conservator Jamie Spears, calling him a “total dick” and claiming that he attempted to make their relationship difficult.
“Now it’s important for people to understand that I have zero respect for someone trying to control our relationship and constantly throwing obstacles our way,” he wrote. “In my opinion Jamie is a total d*ck. I won’t be going into details because I’ve always respected our privacy but at the same time I didn’t come to this country to not be able to express my freedom and opinion.”
June 2021: Sam’s #FreeBritney Support
Right before Spears took the stand during her conservatorship hearing on June 23, Asghari took to his Instagram Story to show his support for Spears as she prepared to speak against her legal arrangement. The model uploaded a selfie wearing a “Free Britney” T-shirt, officially proclaiming his support for the fan-driven online movement. He also added a “lion” emoji, referring to his affectionate nickname for Spears: “lioness.”
The couple that fights for freedom together stays together.
September 2021: The Engagement
On Sept. 12, just hours before the 2021 MTV Video Music Awards, Spears announced her engagement to Ashgari via Instagram. “I can’t f*cking believe it,” she captioned the post, in which she showed off her all-new rock. According to Brandon Cohen, Asghari's manager, the “one-of-a-kind ring” was designed by New York-based jeweler Roman Malayev’s Forever Diamonds. “Britney is ecstatic,” a friend close to the pop star told People.
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