Britney Spears and Sam Asghari's Relationship Timeline

Britney Spears and Sam Asghari have broken up.

On Aug. 16, 2023, multiple sources confirmed to PEOPLE that the couple separated after 14 months of marriage. That same day, Asghari filed for divorce.

Spears and Asghari were first romantically linked after meeting on the set of Spears' "Slumber Party" music video. In the years that followed, the two were seen going on cozy date night dinners and jet-setting to favorite locales, including Hawaii.

The two got engaged in September 2021 and tied the knot the following June in front of about 60 guests — including famous friends Madonna, Paris Hilton, Kathy Hilton and Drew Barrymore.

From their first meeting to their split, here's a look at Britney Spears and Sam Asghari's relationship timeline.

October 2016: Sam Asghari appears in Britney Spears' "Slumber Party" music video

The two first connected after Asghari appeared as Spears' love interest in her "Slumber Party" music video, which was shot in October and released the following month.

November 2016: Britney Spears and Sam Asghari spark dating rumors Sam Asghari and Britney Spears. Sam Asghari/Instagram

In late November 2016, the duo kept people guessing about their relationship when Asghari posted a photo of himself cozied up to Spears while out at a restaurant, which he later deleted.

January 2017: Britney Spears and Sam Asghari go Instagram official Britney Spears Instagram

It wasn't long after a source told PEOPLE in December 2016 that Spears and Asghari were getting to know each other when the model made his first official appearance on her Instagram. They rang in the new year together at Catch LA, where they seemed cozy and in great spirits leading up to a midnight kiss. She seemingly confirmed suspicions of a blossoming relationship with an Instagram post showing Asghari with his arm around her shoulder.

Fans may be surprised to know that their new relationship was nearly a missed connection. After their initial meeting, the Princess of Pop dug up Asghari's phone number out of her bag nearly "five months later," she revealed in a January 2017 radio interview.

"I was like, 'He was really cute, this guy was really cute,' so I called him," she said. "He's just a really fun, funny person."

February 14, 2017: Britney Spears and Sam Asghari spend Valentine's Day together Britney Spears Instagram

Fortunately, it was a match and Asghari became Spears' date to the Clive Davis Pre-Grammy Gala in February 2017, before they spent Valentine's Day in a $30 million villa in Malibu, courtesy of Airbnb, with her sons Sean Preston and Jayden James Federline.

March 3, 2017: Sam Asghari celebrates his birthday with Britney Spears

The following month meant the celebration of Asghari's 23rd birthday.

"My baby's birthday," Spears captioned her set of PDA-packed pictures, which included their hike, cake and fun selfies with more Snapchat filters.

Asghari also gushed about his special cake from Spears that read "Happy Birthday Hesam."

"She calls me by my real name," he wrote on Instagram.

June 6, 2017: Sam Asghari visits Britney Spears during her international tour

As the singer toured in Japan, her first stop on a month-long international tour, Asghari paid her a special visit.

"Came to Japan to see this one @britneyspears," Asghari wrote on Twitter —while Spears wrote earlier, "Thinking of tonight's show has me spinning… just like this night in Vegas. Can't wait to see you, #Osaka!!!"

September 11, 2017: Britney Spears and Sam Asghari go to Disneyland together

Channeling their inner kids, Spears and Asghari spent a day at Disneyland in September 2017, which she marked with a couples' pic on Instagram.

November 29, 2017: Britney Spears and Sam Asghari attend a basketball game together

On Nov. 29, the couple attended a Los Angeles Lakers game together with Spears' two sons, Preston and Jayden, whom she shares with ex-husband Kevin Federline.

January 1, 2018: Britney Spears and Sam Asghari spend New Year's together

The two rang in 2018 together with a cute video to Instagram taken ahead of her final Las Vegas residency show.

"Are you excited about 2018?" Asghari asked Spears, to which she replied in the affirmative.

"You look beautiful," Asghari told his girlfriend.

"Thank you, and I love you," the singer said before giving him a kiss on the cheek as he grinned.

February 5, 2018: Britney Spears gives Sam Asghari a sweet shout-out on Instagram Britney Spears Instagram

In early February 2018, Spears shared a sweet post commemorating their time together.

"I've been with this man for over a year," she captioned a photo of the couple on a hike near a waterfall. "Every day he inspires me to be a better person and that makes me feel like the luckiest girl in the world!! 🌈🌸❤."

April 12, 2018: Britney Spears and Sam Asghari attend the GLAAD Media Awards Britney Spears and boyfriend Sam Asghari. Vivien Killilea/Getty

Spears had Asghari by her side as she was honored with the Vanguard Award during the ceremony.

June 2018: Britney Spears and Sam Asghari take a trip to Miami

Once summer was in full swing, the two took a trip to Miami, where Spears wrote that she was "having the best time with my other half ❤️ ."

April 3, 2019: Sam Asghari supports Britney Spears during her mental health treatment

After her father, Jamie Spears, became seriously ill when his colon spontaneously ruptured in November 2018, the singer revealed that she would be taking an indefinite break from preparing for her next Las Vegas show, Domination, to support her father.

During the tough time, Spears checked into a facility for "all-encompassing wellness treatment" in April 2019. That's when Asghari stepped in to play a bigger role in supporting Spears as she dealt with her father's health scare.

A Spears family source told PEOPLE, "There is no question that Sam is great for Britney. He has a very positive influence on her. He is very motivated to stay healthy and fit, and they often work out together."

Asghari also often cooks healthy meals for the star, and "he is a wonderful boyfriend," the source added.

July 23, 2019: Britney Spears and Sam Asghari attend their first film premiere as a couple Britney Spears and Sam Asghari. Kevin Winter/Getty

In late July 2019, the two posted about attending their first film premiere together as a couple. Spears and Asghari walked the Once Upon a Time in Hollywood red carpet on July 23. The couple happily posed for photos on the carpet and even shared a kiss.

December 2, 2019: Sam Asghari celebrates Britney Spears' birthday

On Spears' 38th birthday that December, Asghari posted a tribute to his "princess" alongside a video of the two ice skating.

"We live, we laugh, we argue, and most of all we LOVE ❤️ There's a reason why the world fell in love with you!" he wrote. "You might be the princess of pop but mostly you're my princess 👸."

Asghari continued: "Biggest Happy Birthday to you @britneyspears 🎆 My Ass still hurts from falling and breaking the ice 😂😂😂😂 you get it?"

June 23, 2021: Sam Asghari supports Britney Spears during her conservatorship battle Sam Asghari and Britney Spears. Sam Asghari/Instagram

In June 2021, Spears spoke at a conservatorship hearing in Los Angeles, spending 30 minutes telling Judge Brenda Penny by phone, "I'm not happy. I can't sleep. I'm depressed. I cry every day."

Following the singer's explosive court appearance, a source told PEOPLE that Asghari — who wore a #FreeBritney T-shirt on his Instagram Story ahead of the hearing — has been the singer's "rock."

"Sam has been Britney's rock for years. He makes sure that she eats well and works out," the source says about Spears' boyfriend. "She leans on him for everything. He works and has his own life too, but is around as much as he can."

It's a sentiment Asghari made clear in February when he spoke to PEOPLE about being by her side following the release of an unauthorized Hulu documentary on Spears' life and conservatorship.

"I have always wanted nothing but the best for my better half, and will continue to support her following her dreams and creating the future she wants and deserves," he told PEOPLE exclusively then. "I am thankful for all of the love and support she is receiving from her fans all over the world, and I am looking forward to a normal, amazing future together."

September 12, 2021: Britney Spears and Sam Asghari get engaged

On Sept. 12, 2021, Asghari proposed to Spears. The couple shared the happy news on Instagram, and Asghari's manager Brandon Cohen shared in an additional statement to PEOPLE that he is "proud to celebrate and confirm the engagement."

"The couple made their long-standing relationship official today and are deeply touched by the support, dedication and love expressed to them," said Cohen, adding that Spears' new ring was designed by N.Y.C. jeweler Roman Malayev.

April 11, 2022: Britney Spears calls Sam Asghari her "husband" on Instagram and reveals that she is expecting Sam Asghari Instagram

On April 11, Spears posted a photo of a pink tea set and matching flowers to her Instagram page along with a lengthy caption about her latest vacation to Maui, leaving many fans wondering if she and Asghari have tied the knot and are expecting their first child together.

"I lost so much weight to go on my Maui trip only to gain it back 🤷🏼‍♀️🤷🏼‍♀️🤷🏼‍♀️ … I thought 'Geez … what happened to my stomach ???' My husband said 'No you're food pregnant silly 🤪 !!!' So I got a pregnancy test," Spears wrote, "and uhhhhh well … I am having a baby 👶🏼 …"

May 14, 2022: Britney Spears and Sam Asghari announce that they have lost their baby

The following month, Spears and Asghari announced in a joint Instagram post that they "have lost" their baby.

"It is with our deepest sadness we have to announce that we have lost our miracle baby early in the pregnancy," they wrote in the post. "This is a devastating time for any parent. Perhaps we should have waited to announce until we were further along, however we were overly excited to share the good news."

June 9, 2022: Britney Spears and Sam Asghari get married Britney Spears Instagram

On June 9, the longtime couple said "I do" in Los Angeles. Around 60 guests were in attendance, including Drew Barrymore, Madonna, Paris Hilton and Selena Gomez.

According to sources, Spears wore a gown by famed fashion house Versace and walked down the aisle to Elvis Presley's "Can't Help Falling in Love."

August 6, 2022: Britney Spears and Sam Asghari respond to Kevin Federline's claims that her sons don't want to see her

Spears and Asghari responded to her ex-husband Federline's comments to The Daily Mail, in which he claimed that his two sons with Spears are choosing not to see her.

Spears shot back with an Instagram Story saying, "It saddens me to hear that my ex-husband has decided to discuss the relationship between me and my children."

"As we all know, raising teenage boys is never easy for anyone. It concerns me the reason is based on my Instagram. It was LONG before Instagram," she continued, referencing Federline's comment about how the boys react to their mom's social media posts.

Spears added, "Only one word: HURTFUL."

Asghari supported his wife with his own Instagram Story. "There is no validity to his statement regarding the kids distancing themselves and it is irresponsible to make that statement publicly," he wrote. "The boys are very smart and will be 18 soon to make their own decisions and may eventually realize the 'tough' part was having a father who hasn't worked much in over 15 years as a role model."

He added that he doesn't know Federline personally, but he has "nothing against him aside from him choosing to vilify my wife."

In a second Instagram Story, Asghari wrote, "I wish him the best and hope he has a more positive outlook in the future for benefit of all involved." He added, "But for now: Keep my wife's name.....out your mouth."

December 2, 2022: Sam Asghari celebrates Britney Spears' 41st birthday

On her birthday, Asghari surprised Spears with cake, flowers and balloons.

"My husband surprised me ✨🎂🎈!!!" Spears wrote on Instagram. "I'm sick with the flu and he came downstairs … he was pretty f---ing smooth !!!! I love you 🥰😘 !!!! It's Mr. and Mrs. Asghari 💍💍💍 !!!"

Asghari shared a behind-the-scenes video of how he prepared the house for his wife's birthday.

"Today's your girl's birthday. Been together for a few years, you're starting to run out of ideas," he can be heard saying in the clip. "You've gotta be creative fellas. You will never have enough balloons. The more, the better. Regular guys just buy flowers, but you're not a regular guy, so you buy a bunch of rose petals and place them like a classic man."

March 31, 2023: Source says Sam Asghari and Britney Spears are not having marital issues

Asghari and Spears were both spotted without their wedding rings, which led fans to believe that the couple had split.

However, Brandon Cohen, a rep for Asghari, told PEOPLE that the pair are not having marital problems despite the rumors. He explained that Asghari wasn't wearing his ring because he was filming a movie.

August 16, 2023: Sources confirm that Britney Spears and Sam Asghari have separated

After months of rumors about marital issues, multiple sources confirmed to PEOPLE that Spears and Asghari split. A source also confirmed that the personal trainer filed for divorce from the pop star. Court documents revealed that the couple separated on July 28 and that Asghari is requesting spousal support.

"Their marriage has been on the rocks for months," a source told PEOPLE. "There has been constant drama. It's sad. A divorce would be devastating for Britney."

A separate insider added: "It's been very toxic between them for a long time."

August 17, 2023: Sam Asghari breaks silence after filing for divorce from Britney Spears

A day after filing for divorce, Asghari shared a statement on Instagram.

"AFTER 6 YEARS OF LOVE AND COMMITMENT TO EACH OTHER MY WIFE AND I HAVE DECIDED TO END OUR JOURNEY TOGETHER," he wrote. "WE WILL HOLD ONTO THE LOVE AND RESPECT WE HAVE FOR EACH OTHER AND I WISH HER THE BEST ALWAYS."

Asghari continued: "S--- HAPPENS. ASKING FOR PRIVACY SEEMS [RIDICULOUS] SO I WILL JUST ASK FOR EVERYONE ... TO BE KIND AND THOUGHTFUL."

The actor's rep, Brandon Cohen from BAC Talent, made a separate statement to PEOPLE.

"There are many claims that Sam is challenging the prenup and threatening to exploit his ex-wife with videos," he said. "However, all these claims are false, as no negative intention has ever been directed towards her and never will be. Sam has always and will always support her."

According to a source, Spears is in "great spirits despite everything going on."

"Obviously it's never an easy thing to go through," the source said, "but she's remaining positive and focusing on the future."

March 2, 2024: Sam Asghari says he'll "never" talk badly about Britney Spears

Asghari harbors no negativity toward Spears or their short-lived marriage.

"It was a blessing to be able to share life with someone for a long time. And people grow apart and people move on," he told PEOPLE. "I never understood when people part ways [and] they talk badly about each other. That's something I'm never going to do because I had nothing but an amazing experience."