The couple has been going strong since they met in 2016

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From the start, it’s been clear that Britney Spears and Sam Asghari are “Crazy” for each other.

It’s been nearly five years since the pair were first romantically linked after meeting on the set of Spears’ “Slumber Party” music video. The cute couple has 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 engaged!

Here's a look back at how it all began:

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.

The duo wasted no time in welcoming the spring, jumping in the pool to show off an impressive trick: Spears standing on her boyfriend’s shoulders, showing off her incredible physique.

The singer then set off for a month-long international tour in Asia, but her boyfriend wasn’t far behind. Before he came to visit in Japan, Spears shared an adorable video of the duo pulling off a dance move.

“Thinking of tonight’s show has me spinning… just like this night in Vegas,” she wrote. “Can’t wait to see you, #Osaka!!!”

The duo went back to their goofy ways after Spears returned to the States, rocking their heads to J. Balvin and Willy William’s hit song “Mi Gente” in a psychedelic Instagram video.

“Me and my boyfriend,” she captioned the post.

And continuing to channel their inner kids, Spears and Asghari spent a day at Disneyland in September 2017, which she marked with a couples’ pic on Instagram.

The pop star shared a holiday-themed video on Instagram to celebrate the beginning of December 2017, in which the pair shared a sweet kiss while having dinner by the lake.

They then showed off their dance moves with Spears twirling in Asghari’s arms in a short, ruffled black dress as he dipped her.

Their romantic holiday season continued into 2018. Asghari shared a cute video to Instagram taken ahead of her final Las Vegas residency show.

“Are you excited about 2018?” he 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!!  🌈🌸❤”

The couple continued to breeze through 2018 while having fun, playing tennis, dancing and working out.

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 ❤️ .”

By July 2018, Spears kicked off her Piece of Me tour, her first since ending her four-year Las Vegas residency, and got a visit from her boo in Belgium.

Suddenly, things for Spears took a turn when 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.

Once Spears was able to take her much-needed time off, she went back on Instagram to confirm to fans that she was still deeply in love with her man.

Soon enough, the couple began showing back up on each others’ social media feeds. 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?"

By early 2020, the couple was sticking close to home amid the beginning days of the COVID-19 pandemic, posting cheeky workout videos, reminding people to dance and promoting masking (and later, vaxxing). But their relationship grabbed even more attention in June 2021, when 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."

He made good on that last statement on Sept. 12, 2021, when he 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.