Britney Spears & Sam Asghari's Relationship Timeline

“Free Britney” has taken on a whole new meaning now that Britney Spears’ latest marriage to Sam Asghari has ended. After a whopping 14 months, news came out that the pop star and model are going their separate ways. While fans were rooting for the two to make it, they couldn’t seem to make it last.

Since this was Britney’s third marriage, many felt this was it, the one where she could live happily ever after. But unfortunately, things didn’t work out that way. Through the ups and the downs, here’s Britney Spears and Sam Asghari’s relationship from beginning to end.

Like many celebrity couples before them, Britney Spears and Sam Asghari met on the video set of her single "Slumber Party" in 2016. The video was a bit of foreshadowing since Sam played Britney's love interest. Sam described having “butterflies” meeting the Britney Spears for the first time.

Even though the two hit it off, exchanged numbers, and planned on having a first date, things didn’t quite work out that way. Britney later admitted in an interview on AMP 103.7's Fast in the Morning with Nathan Fast and Sybil Summers that she only reached out to Sam five months later after digging up his number from her bag.

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Once they reconnected, it was on and popping because the couple made their relationship Insta-official in January 2017. The two grew closer as they dated and shared their love with the world. Social media posts showed that their relationship was blossoming.

One of the first major tests of Britney’s and Sam’s relationship came when Britney checked herself into a wellness facility in April 2019. Sam proved that he was ten toes down with Britney Spears because he stayed with her throughout her stay. Once she finished her program the following month, Britney took to IG to let everybody know, “I love this man.”

By July 2019, the couple’s relationship really heated up when Britney was caught out in public with a diamond ring. As fans wondered what was going on, the two kept things on the low, and Sam denied they were engaged.

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As the #FreeBritney social media campaign picked up speed throughout 2021, Sam supported freeing his lady from her conservatorship overseen by her father, Jamie. Sam publicly called out Jamie for trying to meddle in his and Britney’s relationship. Sam wrote on social media he had “zero respect” for somebody trying to control their relationship and throwing obstacles in their way. He added Jamie was “a total d*ck.”

A few months later, Sam posted a selfie of himself wearing a “Free Britney” t-shirt and posted a lion emoji as an homage to his “lioness.” Britney matched Sam’s same energy when she spoke in court about her conservatorship. She said she saw a long-term relationship with Sam, including getting married and having a baby. Britney mentioned how she wanted to remove the IUD she had in order to have Sam’s baby.

Britney’s dream came true when she and Sam got engaged in September 2021 where she posted a video on IG with Sam by her side. As she flaunted her huge diamond, Sam was smiling ear to ear. She captioned the video, “I can’t f*cking believe it,” followed by six ring emojis.

The good times kept rolling in when Britney’s 13-year conservatorship ended that November. Britney and Sam were finally free to live their best life with no strings attached. That led to the lovebirds announcing in April 2022 that the 40-year-old mother of two was expecting her first child with 28-year-old Sam. The two were over the moon.

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Unfortunately, Britney announced in May that she and Sam had lost their “miracle baby.” They wrote on IG, “It is with our deepest sadness we have to announce that we have lost our miracle baby early in the pregnancy.”

The two looked at the bright side and wrote, “Our love for each other is our strength. We will continue trying to expand our beautiful family.” Sam commented they would “have a miracle soon.”

Despite the loss the two suffered, they persevered and made it to their big day…but there were a few hiccups. Before the big day on June 9, 2022, Britney’s first husband, Jason Alexander, who she was married to for 55 hours in 2004, decided to crash her wedding. The whacky ex broke into her home and filmed himself running around trying to find his former wife. Although he claimed he was invited by Britney herself, security wrestled him to the ground and kicked him to the curb.

Thankfully, all that messiness was cleared up before Britney and Sam exchanged their vows. The intimate ceremony took place in front of the likes of Madonna, Donatella Versace, Selena Gomez, Drew Barrymore, and Paris Hilton. Britney and Sam never looked happier, but would it last?

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Over time, fans and the public began to notice a breakdown in Britney’s well-being, like troubling social media posts, including nude photos, and publicly arguing with her two sons. Throughout it all, Sam defended his wife and remained by her side, but one public incident gave an unprecedented glimpse into their private lives.

In January 2023, while the newlyweds were dining out at Joey in Woodland Hills, reports surfaced that Britney “caused a scene.” Witnesses described her as acting “manic” and “talking gibberish.” How did Sam handle it? He walked out.

However, other sources say that Britney reacted to being taunted by another diner, and Sam only walked to the car and returned. It didn’t really matter the real situation because the rumor mill had already started – was there trouble in paradise?

Adding fuel to the fire was the fact that Britney’s loved ones became so concerned about her that they staged an intervention to get her some help. Her inner circle spoke about drug use and taking meds that made her erratic. Sam, along with her manager, doctors, and an interventionist, planned to take Britney to a rented house in February.

Britney caught wind of what was going on behind her back, and the whole plan was scrapped. With Britney and Sam being on two separate pages about her behavior and what was best for her, major splinters formed in their relationship.

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By May 2023, numerous insiders reported that trouble had been brewing for a while between Britney and Sam. These sources said the couple was dealing with extreme difficulties, including physical altercations. They were also reportedly arguing more and more, with things getting so intense that security had to step in.

Sam complained Britney was the actual aggressor and claimed that she attacked him while he was asleep. According to his claims, this aligns with the time the paparazzi spotted him out with a black eye. Photographers also noticed he had bite marks on his forearm. Sam also expressed concern over Britney’s fascination with knives.

And, to top it off, Sam accused Britney of cheating on him. He became so fed up with Britney and her behavior that he reportedly started spending more time away from the marital home.

By August 16, Sam was finally done and filed divorce papers. Sources claimed that a “nuclear fight” in June was the final straw. There was also talk that Sam would challenge his prenup, which Britney had insisted he sign. Some said Sam was trying to walk away with “hush money” to prevent him from airing Britney’s dirty laundry.

At first, both parties remained silent on the divorce news, but Sam spoke out days later. On his Instagram story, he wrote that the couple decided to end their journey. He added, “We will hold onto the love and respect we have for each other and I wish her the best always. Sh*t happens.”

Britney reportedly was making the best of the situation. Days later, Britney posted a video of herself on Instagram dancing to “If” by Janet Jackson. She wrote that six years was a long time to be with someone, and she was a little shocked by the breakup. However, she said she couldn’t take the pain anymore. Britney added, “I will be as strong as I can and do my best!!!” Hopefully, both Britney Spears and Sam Asghari will stay strong through this very public breakup and get the support that they each need.