Very few people have had a tougher 2019 than Britney Spears.

The iconic pop star saw her year quickly spiral out of control shortly after leaving 2018 behind, as her father Jamie Spears‘ near-fatal colon rupture prompted her to cancel her impending residency at the Park MGM in Las Vegas, go on an indefinite work hiatus, disappear from social media, and eventually enter into treatment to focus on self-care amid all the stress. 

Questions over just what was going on in Britney’s world would ignite a movement among fans, turning the hashtag #FreeBritney into something of a call to action, as an investigation into her decade-long conservatorship was ordered by the judge on her case. While the results of the probate court’s inquiry into the case remain to be seen, Brit’s only just begun to come out the other side of her truly trying past six months. 

She’s returned to social media in a big way, embarked on several relaxing getaways, and even made a surprise red carpet appearance at the July 22 premiere of Once Upon a Time in Hollywood. 

And she’s done it all with ride-or-die boyfriend Sam Asghari by her side. 

While the jury’s still out on whether the gorgeous diamond ring Britney was rocking on that finger means anything significant—her rep hadn’t returned E! News’ request for comment as of press time—the appearance at the Quentin Tarantino film’s Los Angeles premiere did mark a major milestone in her relationship with Sam, as it was the first time the two have walked red (or pink, if we’re being technical) carpet together since meeting on the set of her “Slumber Party” music video in late 2016. 

“I was excited that I [would] get to meet one of the biggest artists of all time,” Sam, who was hired to play Britney’s love interest in the video, recalled to Men’s Health in July of last year. “I had butterflies.”

As the singer, who had been single since splitting with Charlie Ebersol in June 2015, explained to AMP 103.7 in January 2017, it was the sort of downtime that’s unique to set life that allowed for a spark to ignite between herself and the now 25-year-old model.

“We were waiting and waiting together for 20 minutes at a time, literally stuck there,” she recalled. “We were forced to talk to each other.”

While Sam’s initial stab at humor didn’t go over so well—”She said, ‘Hi, I’m Britney,’ and I said, ‘I’m sorry, what’s your name again?'” he told Men’s Health. “I tried to be funny. I don’t think anybody got it”—talk soon turned to one of their favorite foods, sushi, and numbers were eventually exchanged so the two could enjoy a meal together IRL. 

“I found his number in my bag. I was like, ‘He is really cute. This guy is really cute,'” Britney told the radio station. “So then I called him, and ever since then, he is just a really fun, funny person.”

While the two attempted to keep their relationship quiet in its early days, with paparazzi only spotting them out on a date in December, Sam told the fitness mag that the secrecy had nothing to do with the nature of the relationship. “After the video came out, nobody knew we were dating,” he said. “I don’t think [she or I] had the intention to just be friends.”

By New Year’s Day 2017, Britney would finally make things Insta-official by sharing a photo of Sam putting his arm around her at dinner.

As Britney focused on the final days of her Las Vegas residency, which officially closed on December 31, 2017 almost exactly four years after it began at the Planet Hollywood Resort & Casino, she and Sam documented nearly all their time spent together on social media, giving fans a peek at their travels and their shared sweat sessions.

“Working out together is always nice and we try to do it a couple times,” Sam told Men’s Health. “It’s super healthy, mentally and physically. It takes your mind off of everything else.”

Though, as Brit revealed during a 2018 interview with the Associated Press, he can be a bit of a taskmaster when it comes to filming their exploits in the gym. “He’s a trainer so everything has to be so perfect. We probably did 40 (takes) and I hurt myself,” she joked. “It looked great, he did a good job and he edited it really, really well.”

Settling into life post-residency, the two began to find that they inspired one another in more ways than perhaps they’d initially realized. “I’ve been with this man for over a year,” Britney wrote on Instagram in February 2018. “Everyday he inspires me to be a better person and that makes me feel like the luckiest girl in the world!”

“She motivates me more than anyone. It’s crazy how I can be humbled by a person like her. If I could be that humble when I’m that high in life, that would be the best thing,” Sam told Men’s Health. “I grew up with three sisters, and my personality is just to be a supportive person for my family and she’s family. I’m always going to support her. She is another blessing that happened to me.”

It wasn’t until this year, however, that that support was put to the test. 

After Britney pulled the plug on her new “Britney: Domination” residency in January, telling the world she intended to “[dedicate] my focus and energy to care for my family” instead, and then revealed she’d checked into a mental health treatment facility in April, Sam took to social media to vocalize his support for his love.

“It isn’t weakness,” he wrote on his Instagram Story. “It’s a sign of absolute strength, people should only be inspired by this, at least I am.”

In spite of what Britney’s social media hiatus had led some fans to believe, an insider assured E! News at the time that two were “very much still together.”

“Sam has stuck by her side throughout all of her recent struggles and knows that this is just a phase in Britney’s life that they will have to adjust to right now,” the source added, explaining that Sam had been “very helpful in making sure Britney did whatever she needed to feel better.” That included him checking in on her and being “by her side.”

While fan concern over the Princess of Pop grew throughout the year, Sam played a vital role in Britney’s life. “Sam has been an absolute dream come true for Britney,” a source told Us Weekly in late May. “He is such a positive light in her life. No one makes her smile this much—other than her boys [Preston, 13, and Jayden, 12], of course.”

“Sam is really in love with Britney. He will always be there to help in any way he can. He’s her protector,” an insider told Entertainment Tonight in June. “When they’re together, they cook at home most nights. They like to keep things relaxed and simple.”

By then, Britney had completed treatment and embarked on a romantic getaway in Miami with her beau, where the couple recreated the iconic Titanic scene on the bow of a yacht together. 

“Britney and Sam took a quick weekend trip to Miami,” a source told E! News. “All [Spears] wanted was to be in a bikini by the water. She was so excited to be able to go. They had a room overlooking the ocean and Britney was in heaven.”

The time away with Sam was just what the pop star needed. “Britney was having the best time laughing and being with her man,” our insider added. “They went swimming, laid out, stretched together and had someone take their pictures doing all different poses and angles. They held hands and kissed. Britney couldn’t have looked any happier or more content.”

“Sam was taking care of her with towels and whatever she needed,” our source continued. “He arranged for a golf cart to take them down to the beach and back to their room. He dotes on her and it seems like his priority is for Britney to have fun and be happy. She got her wish and had a great weekend.”

When not on holiday, Sam also makes it a priority to be a part of the lives of Brit’s boys, whom she shares with ex-husband Kevin Federline. And that’s something that’s paramount for the doting mom. “For Britney, being a mother is the most important part of her life,” a source told ET last month. “She is the most content whenever she is around her boys. Sam is also very involved with the kids’ lives. The boys appreciate it when they all spend time together as a family.”

“Her kids love when Sam is around,” the source continued. “They have from the beginning of the relationship. He gets along with all of them very well.”

While it remains to be seen what, if anything, the rock on her finger means, it’s clear that Britney has found a more important rock in Sam. And after all she’s been through, that’s a beautiful thing.