Britney Spears and Sam Asghari's Relationship Timeline

Sam Asghari smiles as fiancé Britney Spears puts a hand on his shoulder

Scroll through the Instagram accounts of Britney Spears and Sam Asghari, and you’ll see a seemingly normal couple just like any other: They travel together. They sweat to synchronized workouts. They pose in front of the Christmas tree. But, their road to relationship bliss hasn’t been all rainbows and butterflies. In addition to the constant scrutiny they face as one of the most famous duos in the world (even Octavia Spencer has weighed in on their affairs), much of their time together has been spent with Britney, now 40, living under an conservatorship that was imposed upon her when she was roughly 27 years old.

Britney testified to a court in June that big decisions facing the twosome, such as when to wed or whether to have children, were not always theirs to make. Now free to be her own woman after Judge Brenda Penny ruled that her conservatorship was “no longer required” in mid-November, the couple, who got engaged in September, is embarking upon what is sure to be their best chapter yet. But first, we’re recapping their journey to true love below.  

  • The couple has been dating five years.
  • They met on the set of her music video, “Slumber Party.”
  • Britney made the first move, picking up the phone to call Sam five months after they first exchanged numbers.
  • The pop star, who was previously married to childhood pal Jason Alexander and backup dancer Kevin Federline, has revealed that she’ll walk down the aisle in a custom gown by Donatella Versace.
  • Britney announced the couple are expecting a baby!
01 of 23

2016: An Instant Connection

Britney and Sam first crossed paths in 2016, when he landed a role in her music video for her song, “Slumber Party.” The “Toxic” singer opened up about the moment they clicked to CBS Radio in January 2017. “We were doing the scene where I was doing the walk scene through the hall to go through the door to go to the bedroom, and we were sitting there and waiting and waiting together for like 20 minutes at a time," she revealed. "We were having to be literally stuck there together, so we were basically forced to talk to each other. We started talking about sushi and started talking about things we like, and, like, we should go to sushi one day. 'Let's do this, let's do this.' And he said, 'OK, I'll give you my number after the thing.'"

Sam later shared his own remembrance of the events to Men’s Health, recalling how jazzed he was to meet the musical icon. “I was excited that I get to meet one of the biggest artists of all time,” he told the outlet. “I had butterflies.”

When his big moment came, the model tried to break the ice with a little good, old-fashioned humor. Recalled Sam: “She said, ‘Hi, I’m Britney,' and I said, ‘I’m sorry. What’s your name again?’ I tried to be funny. I don’t think anybody got it.”

02 of 23

2016: Making the First Move

While nothing happened initially following the pair’s meet-cute, fate stepped in when the Crossroads actress was reminded of their introduction. “I kept his number, and it was so weird—it was like five months later, and I found his number in my bag," she told CBS Radio. “I was like, ‘He is really cute. This guy is really cute.’ So then I called him, and ever since then, he is just a really fun, funny person.”

03 of 23

November 26, 2016: Dinner à Deux

Britney may have made the first move, but Sam was the first to flaunt his new love on social media, posting a now-deleted photo at dinner with the performer to his Instagram. According to Us Weekly, he captioned the shot, “You totally are banging! Lol.”

04 of 23

January 1, 2017: Auld Lang Syne

By the New Year, there was no denying the couple’s off-screen connection. Britney introduced her followers to her new beau with a photo of them cuddled up for the holiday.

05 of 23

March 16, 2017: Meeting the Fam

Designer Michael Costello inadvertently revealed that Sam was ready to introduce the princess of pop to his family when he posted a photo for the couple sitting front row at his STELLO fashion show in March (Sam's sister Fay, was a model in the show).

06 of 23

June 5, 2017: A Grand Gesture

No distance could keep the fledgling pair apart—Sam flew all the way to Japan to be with her—and help her practice her pre-show moves in her dressing room—in June.

07 of 23

September 9, 2017: The Happiest Place on Earth

Brit and Sam were all smiles in September 2017 when they headed to the House of Mouse for a little summertime magic. According to Us Weekly, the pair were there to celebrate Britney's two sons with ex-husband Kevin, Jayden and Preston, whose birthdays fall on September 12 and September 14, respectively.

08 of 23

November 29, 2017: Sitting Courtside

Britney Spears laughs with boyfriend Sam Asghari's arm around her.

The couple was spotted sharing a laugh together at a Lakers game in Los Angeles against the Golden State Warriors in November.

09 of 23

December 2, 2017: Birthday Bonanza

One month later, the model went all out for his girlfriend’s birthday. In a video posted to his Instagram, Britney is seen kneeling down to blow out candles on a group of cupcakes next to a heart outlined with candles and rose petals. Sam wasn’t shy about expressing his emotions publicly, either, writing, “Thank you for being you, thank you for showing me the true meaning of a beautiful woman and a strong mother, and most of all thank you for being mine.” He closed the swoon-worthy message by saying that he considers himself the “luckiest man on the planet”—aww!

10 of 23

February 2018: One Year Down

In February, it was Britney’s turn to shower her significant other with praise. “I’ve been with this man for over a year,” she captioned a photo of the pair looking fit in front of a waterfall. She added: “Every day he inspires me to be a better person and that makes me feel like the luckiest girl in the world!”

11 of 23

April 12, 2018: A Proud Moment

Britney Spears looks gorgeous in a silver strappy gown next to boyfriend Sam Asghari in a tux

Sam was by his girlfriend’s side in April, when she was honored at the GLAAD Media Awards in Los Angeles with the organization’s prestigious Vanguard Award—a dignity bestowed upon notable persons who have made an effort to elevate the equality and acceptance of the LGBTQ+ community.

12 of 23

July 20, 2018: Laying Down Roots

After a year-and-a-half together, the personal trainer opened up about his relationship with the pop star to Men’s Health. “She motivates me more than anyone,” he raved. “It’s crazy how I can be humbled by a person like her.”

The athlete also made it clear that he had his partner’s back—no matter what. “I grew up with three sisters, and my personality is just to be a supportive person for my family, and she’s family," he said. "I’m always going to support her. She is another blessing that happened to me."

13 of 23

April 2019: Showing Support

Sam made good on his word in April 2019, when he was quick to speak out on the Grammy winner’s behalf after she reportedly checked into a mental health facility. Reposting a meme from her account about taking care of one’s mind, body, and spirit, the fitness guru wrote, “It isn’t weakness, it’s a sign of absolute strength, people should be inspired by this, at least I am. <3”

14 of 23

July 22, 2019: A Grand Debut

Britney Spears and Sam Asghari kiss on the red carpet.

The pair made their grand red carpet debut at the L.A. premiere of Once Upon a Time in Hollywood, where they not only shared a few kisses for the camera, but sparked engagement rumors thanks to the shiny bauble Britney wore upon her left finger.

15 of 23

May 11, 2020: Getting Fit Done

On the heels of the COVID-19 pandemic, the twosome showed the world how they were spending their quarantine time with an adorable clip of themselves being goofy and working out side-by-side. According to Sam, who later spoke to Men's Health about the video, their final cut, which sees them sparring, lifting weights, and jumping up and down in synchronicity, took a whopping 40 takes to get just right. (Worth it.)

16 of 23

March 6, 2021: Baby Fever

Sam left little doubt as to his intentions for his future with his lady love while speaking to Forbes earlier this year. “I want to take my relationship to the next step," he declared. More importantly, however, he revealed that he was ready to expand his family with the “Stronger” songstress. "I don’t mind becoming a father,” he said. “I want to be a young dad."

17 of 23

August 26, 2021: Her Biggest Fan

The former Mouseketeer acknowledged Sam’s love and support throughout her conservatorship in an August 2021 post on Instagram, writing, “Not only has this cute a**hole been with me through both the hardest and best years of my life, but he happens to be an extremely good cook.” She also threw her own support behind her partner’s endeavors, adding, “Fast & Furious franchise, don’t miss out on your next star!”  

18 of 23

September 12, 2021: Betrothed

After five years together, Sam popped the question to his lady love, as the pair showed off together with a hilarious video of Britney flashing her brand new bling and covering her mouth in disbelief. “I can’t f*cking believe it!!!!!!!” she wrote alongside six diamond ring emojis.

19 of 23

November 12, 2021: Let Freedom Ring

November 12, 2021 didn’t just mark the immediate cessation of Britney Spears’ conservatorship: It also marked a major milestone for the couple, ensuring that they would be able to follow through with their plans to marry. As attorney Sarah Wentz of Fox Rothschild explained to Variety in September, Britney would not have been able to personally sign off on a marriage license while under her conservatorship, leaving her vulnerable to the possibility that it could be invalidated, should her conservator refuse to sign it—a worry she need no longer be concerned with.

Sam showed his support for his other half on the joyous occasion with a meme reading, “Freedom.” “History was made today,” he announced to his followers. “Britney is free!”

20 of 23

November 9, 2021: Putting the Wheels Into Motion

Britney revealed that her wedding planning was well underway—at least as far as her dress was concerned—with a telling Instagram post in early November. “No … this is not my wedding dress 👗 bahahah !!!!” she captioned a photo of herself in a gorgeous pink ball gown. “Donatella Versace is making my dress as we speak 🤫”

21 of 23

November 18, 2021: Big Plans

Sam revealed his plans for the couple’s nuptials while attending the L.A. premiere of House of Gucci. While he told ET that most of the details will be up to his future wife ("It's up to her. She's wearing the pants now!"), he did hint that if he has his way, their ceremony won’t exactly be small and intimate. "I want the biggest wedding in the world!"

22 of 23

December 2, 2021: Romantic Getaway

The pair celebrated Britney’s 40th birthday with a special getaway. “Me and my fiancé are so excited to be going away,” the performer wrote on a shot of her and Sam embracing. Sam shared a similar shot, along with a sweet celebratory message for his future bride. “I call you Lioness because I admire your relentless strength, I’m inspired by your beautiful heart, I celebrate your smile that lights up my world ❤,” he gushed. “Every day is your birthday my queen 👑 Happy 1st birthday to my wife.”

23 of 23

April 11, 2022: Britney is Pregnant

Britney announced on April 11 that she and Sam are going to have their first baby together. The singer shared the big news on Instagram by explaining that she was confused why she was gaining so much weight after a trip to Maui with her fitness trainer fiancé. "So I got a pregnancy test … and uhhhhh well … I am having a baby,” she said in her caption. 

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