Britney Spears and Sam Asghari's Relationship Timeline

From the start, it's been clear that Britney Spears and Sam Asghari have a lot of love for each other.

The pair were first romantically linked after meeting on the set of Spears' "Slumber Party" music video, and they've been inseparable since, going on cozy date night dinners, attending friends' birthday parties and jet setting to favorite locales including Hawaii.

In between hitting the gym, hiking and traveling, Spears is busy documenting her love fest with her beau on social media. And now, the two are married!

After getting engaged in September 2021, the couple tied the knot in Los Angeles in front of about 60 guests — including famous friends Madonna, Paris Hilton, Kathy Hilton and Drew Barrymore.

Take a look back at their relationship timeline below.

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.

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.

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."

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.

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.

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!!!"

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

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

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.

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!!  🌈🌸❤"

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

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 ❤️ ."

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.

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.

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! You might be the princess of pop but mostly you're my princess 👸 Biggest Happy Birthday to you @britneyspears 🎆 My Ass still hurts from falling and breaking the ice 😂😂😂😂 you get it?"

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."

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.

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 👶🏼 …"

The "Oops!... I Did It Again" singer left fans in a tizzy with the post's wording, as many wondered if it served as a pregnancy announcement.

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."

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."