It’s safe to say Rihanna and A$AP Rocky both have “Love on the Brain!”

The musical pair were close friends for nearly a decade before their longtime friendship blossomed into a romantic relationship. Since PEOPLE confirmed their relationship in November 2020, the couple has been spotted out together frequently, on dates and on vacation together.

On May 19, 2022, PEOPLE confirmed that Rihanna and A$AP Rocky welcomed their first child, RZA Athelston. “Rihanna is doing well,” a source told PEOPLE. “They are very excited to be parents. Rihanna is already a wonderful mom.”

In February 2023, Rihanna revealed she was pregnant with her second child as she debuted her baby bump at the Super Bowl Halftime show. In August, sources confirmed to PEOPLE that she and A$AP Rocky had welcomed their second child, Riot Rose Mayers.

Read on to see the evolution of Rihanna and A$AP Rocky’s romantic history, from a sultry performance at the 2012 MTV VMAs to welcoming their two children.

September 6, 2012: Rihanna and A$AP Rocky collaborate and perform together

Nearly a decade ago, RiRi may not have been penning a “Loveeeeeee Song” for Rocky, but the pair’s friendship was kicking off. The singer had the rapper record a verse for the remix of her song “Cockiness (Love It)”; the pair then put on a steamy show while performing the song during the 2012 MTV Video Music Awards, showing off their chemistry even then.

March 2013: A$AP Rocky joins Rihanna on tour

The rapper, born Rakim Mayers, served as the opening act during the North American leg of Rihanna’s Diamonds World Tour.

September 25, 2013: Rihanna stars in A$AP Rocky’s music video

Life imitates art! Seven years before they’d officially become an item, the pals once again proved they’d make a gorgeous pair when they portrayed a couple for the rapper’s “Fashion Killa” music video.

June 2018: Rihanna and A$AP Rocky attend Paris Fashion Week together

Fast-forwarding a bit: the longtime pals made a strikingly stylish pair in coordinating black-and-white outfits while sitting front row at the Louis Vuitton Menswear Spring/Summer 2018 show together during Paris Fashion Week.

September 13, 2018: A$AP Rocky attends Rihanna’s annual Diamond Ball

As longtime friends, it came as no surprise to see Rocky on the guestlist for Rihanna’s annual Diamond Ball, which serves as one of fashion’s biggest nights and a fundraiser for her Clara Lionel Foundation.

December 2, 2019: Rihanna and A$AP Rocky hit their first red carpet together

The pair caused quite the stir when they walked the red carpet together for the British Fashion Awards. During an interview co-hosted by GQ and Vogue, Rocky revealed to Rihanna that her look that night was his “favorite outfit” of hers.

According to Billboard, she designed the Fenty tuxedo he wore.

August 2020: Rihanna and A$AP Rocky collaborate for Fenty Skin

Rocky joined Rihanna’s debut Fenty Skin campaign in 2020, sending the Internet into yet another tizzy when the pair began doing press to promote the campaign — notably including their “Face to Face” video interviews for GQ and Vogue, in which they asked each other rapid-fire questions ranging from what their skin is like to the last thing they bought for under $20.

November 2020: PEOPLE confirms Rihanna and A$AP Rocky’s romance

A source confirmed that the longtime friends were officially an item in November, after months of romance rumors following Rihanna’s split from her boyfriend of three years, billionaire Hassan Jameel, in January 2020.

December 2020: Rihanna and A$AP Rocky vacation in Barbados together

The newly-minted couple took a romantic getaway to Rihanna’s native Barbados for their first holiday together. A source told PEOPLE at the time that “A$AP joined her [in Barbados] and they are spending Christmas together with Rihanna’s family.”

“They’ve been inseparable the past few weeks,” a source told PEOPLE. “It’s a new relationship, but they both seem very into it.”

The source added, “They’ve always seemed to have a great time together,” continuing, “They have a lot in common.”

January 2021: Rihanna Supports A$AP Rocky’s Shoe Line

The fashion mogul showed support for her beau on Instagram by posting a sultry shot of herself wearing a pair of heels that the rapper designed. The crystal-embellished gladiator sandals are a collaboration between Amina Muaddi and Rocky’s creative agency, AWGE.

May 2021: A$AP Rocky opens up to GQ about his feelings for Rihanna

The “Wild for the Night” rapper got candid about his leading lady in GQ‘s June/July 2021 cover story, referring to Rihanna as the “love of my life” and “the one.”

Describing what it’s like to be in a relationship, Rocky said, “So much better. So much better when you got ‘the One.’ She amounts to probably, like, a million of the other ones.”

He continued, “I think when you know, you know. She’s the One.”

May 2021: Rihanna and A$AP Rocky talk about having kids

Speaking about potentially starting a family one day, Rocky told GQ that it is “in my destiny, absolutely.” He added, “I think I’d be an incredible, remarkably overall amazing dad. I would have a very fly child. Very.”

Previously, Rihanna told British Vogue in May 2020 that she wants kids without a doubt.

“I’ll have kids — three or four of ’em,” said the singer, who added without hesitation that she would raise them as a single mother if there wasn’t a man in her life.

“I feel like society makes me want to feel like, ‘Oh, you got it wrong … ‘ They diminish you as a mother if there’s not a dad in your kids’ lives,” Rihanna said. “But the only thing that matters is happiness — that’s the only healthy relationship between a parent and a child. That’s the only thing that can raise a child, truly, is love.”

September 13, 2021: Rihanna and A$AP Rocky make their red carpet debut at the Met Gala

The pair picked fashion’s biggest night to make their red carpet debut, dressing in coordinated looks for the event.

Rihanna arrived in an oversized black sculptural coat dress, while A$AP complimented her with a pop of color in a quilted blanket look.

January 31, 2022: Rihanna announces she’s expecting a baby with A$AP Rocky

Rihanna revealed she was expecting her first child with A$AP Rocky on Jan. 31, after she was photographed showing off her baby bump in New York City.

February 11, 2022: A$AP Rocky and Rihanna coordinate on the red carpet at the Fenty Beauty Universe Event in Los Angeles

Rihanna and A$AP Rocky appeared on the red carpet together at the Fenty Beauty Universe Event in Los Angeles on Feb. 11, 2022. The couple coordinated in purple and green, which, according to Rihanna, was unplanned. “That always happens with us,” she told PEOPLE at the event. “We get dressed in completely separate [areas] across the house, and we leave looking coordinated somehow.”

February 12, 2022: Rihanna and A$AP Rocky make a surprise appearance at Rihanna’s Savage X Fenty store

That following weekend the singer and rapper surprised a group of shoppers at Rihanna’s Savage X Fenty store at the Westfield Culver City mall. The L.A. brick-and-mortar retail store was one of the first to open in early 2022. The couple posed for pictures in front of mannequins which featured lingerie pieces from Rihanna’s Savage X Fenty’s Valentine’s Day collection.

March 6, 2022: Rihanna and A$AP Rocky shop for baby clothing at Baby Dior in Paris

Rihanna and A$AP Rocky were spotted shopping in Paris on March 6, 2022. The expectant parents made a late-night stop into Baby Dior on Avenue Montaigne for baby clothes. Rihanna had already been in the city for Paris Fashion Week the week before.

April 1, 2022: Rihanna wears ‘Baby Daddy’ T-shirt on a casual dinner date with A$AP Rocky

Rihanna and A$AP Rocky held hands on their way to enjoy a casual dinner date together on April 1, 2022. Rihanna sported a white T-shirt with photos of Mickey Mouse and Minnie Mouse that read, “Who Dat Is? Dat’s Jus My Baby Daddy,” while Rocky wore a navy zipper hoodie with reflective sleeves. Together they wore matching AWGE trucker hats to complete the look.

The couple ate at Craig’s restaurant in West Hollywood, Calif. A source told PEOPLE they “had an early dinner … and left around 8.” The insider also noted the mom and dad-to-be “held hands a lot and looked really happy.”

April 23, 2022: Rihanna and A$AP Rocky enjoy dinner following his arrest earlier that week

Three days after A$AP Rocky’s arrest for an alleged shooting, he and Rihanna enjoyed a night out and had dinner at Giorgio Baldi in Santa Monica, Calif. A source told PEOPLE that the couple was joined by a small group of close friends.

“It was a happy and relaxed group,” the source said. “Rihanna looked great. She sat next to A$AP Rocky, and they were affectionate. They dined for a couple of hours. The focus was very much on Rihanna and the baby.”

May 5, 2022: Rihanna and A$AP Rocky “pretend” to tie the knot in a music video

On May 5, 2022, A$AP Rocky dropped his “D.M.B” music video featuring girlfriend Rihanna. The music video was written, directed and executive produced by A$AP Rocky, and, according to a press release, is an “ode to the classic love story.”

The video was shot in the style of a vintage video montage. By the end, Rihanna is wearing a red veil and dress at what appears to be a wedding ceremony. “I was lost then, but I found you/I was slim thick with a bounce too,” Rocky raps. “It’s your tough love that I’m bound to/I f— it up, then it’s round two.”

May 2022: Rihanna and A$AP Rocky welcome their first child

On May 19, PEOPLE confirmed the couple welcomed their first child together.

“Rihanna is doing well,” said the source. “They are very excited to be parents. Rihanna is already a wonderful mom.”

May 30, 2022: A$AP Rocky opens up about fatherhood nearly one month after Rihanna gives birth

A$AP Rocky opened up about fatherhood to Dazed magazine just a few weeks after Rihanna gave birth to their first child. In an interview published on May 30, 2022, Rocky shared how he hopes to raise his kids and the type of father he plans to be.

“I will always remind my children to never lose their imagination, even as adults, no matter what,” Rocky said. He added that he hopes to “raise open-minded children” and “not people who discriminate.” He continued, “And I’m not trying to describe a saint, but realistically, I just want a cool child with cool parents.”

August 23, 2022: Rihanna and A$AP Rocky step out in New York

Rihanna and A$AP Rocky were photographed going out in New York City. The two looked comfortable and casual, with Rihanna in a blue No. 99 football jersey and Rocky wearing a white T-shirt and blue patterned pants.

The couple’s evening outing followed Rocky’s Aug. 17 court appearance, where he pleaded not guilty to two counts of assault with a firearm during a November 2021 incident in Los Angeles.

September 9, 2022: Rihanna supports A$AP Rocky and his whisky line at an event in New York

Rihanna joined A$AP Rocky at a Mercer & Prince event, celebrating the rapper’s new whiskey line. The singer wore a chic black dress and a diamond necklace while Rocky switched between a white tee and a multicolor crewneck.

Clips of the famous couple at the event gained plenty of attention on Twitter, including a video of Rocky putting his arm around Rihanna as she whispers into his ear.

October 2, 2022: Rihanna and A$AP Rocky celebrate his birthday in Hollywood

Rihanna and A$AP Rocky were photographed heading to the Olivetta restaurant in West Hollywood to celebrate the rapper’s 34th birthday a day early.

For the outing, Rihanna wore a ruched black gown with a slit on the left leg, which she paired with an oversized leather jacket. Meanwhile, A$AP Rocky was seen in a black suit and tie.

October 26, 2022: Rihanna and A$AP Rocky attend the Black Panther: Wakanda Forever premiere

Rihanna and A$AP Rocky walked the red carpet at the premiere of Marvel’s Black Panther: Wakanda Forever. Rihanna’s single, “Lift Me Up,” appears on the soundtrack of the Marvel sequel.

The songstress wore a strapless green Rick Owens dress to the event, which she accessorized with a pair of long gloves. Meanwhile, Rocky looked casual look in an oversized khaki jacket and matching pants. The couple posed for photographers with their arms wrapped around each other.

November 7, 2022: Rihanna says A$AP Rocky encouraged her to do the Super Bowl Halftime Show

In September 2022, Rihanna was announced as the headliner for the 2023 Super Bowl Halftime Show.

“I often get so overwhelmed and intimidated by stages like that, so Super Bowl is huge,” she told Access. “[A$AP] was one of my biggest supporters in making my decision to do the Super Bowl. He was like ‘You got this. You can do this.’ “

The Love on the Brain singer went on to gush about her partner and their rock-solid relationship.

“It’s amazing to have a friendship be the center of our entire family. I really love it,” Rihanna said.

January 10, 2023: Rihanna and A$AP Rocky attend the Golden Globes

A$AP Rocky joined Rihanna at the 2023 Golden Globes, where the singer was nominated for best original song for “Lift Me Up” from the Black Panther: Wakanda Forever soundtrack. Rihanna wore a ruched black gown, velvet gloves and a velvet wrap cape while Rocky chose a monochromatic suit by Bottega Veneta.

January 18, 2023: A$AP Rocky says he’s “excited” for Rihanna’s Super Bowl performance

During an interview with Apple Music’s Zane Lowe, A$AP Rocky gushed about the mother of his child.

“I’m so glad that my lady’s back making music again and whatnot, and getting back out there. It’s just incredible,” he said.

The rapper went on to talk about Rihanna’s highly anticipated 2023 Super Bowl Halftime performance.

“The Super Bowl is huge, and her being the creative she is, she going to bring it, man. I’m excited. I’m more excited than everybody else, honestly,” A$AP said.

February 12, 2023: Rihanna and A$AP Rocky are expecting their second baby together

A rep for Rihanna confirmed to PEOPLE that the singer was pregnant following her halftime performance at Super Bowl LVII. Rihanna revealed her baby bump during the opening moments of her show, rubbing her stomach and leaving the front of her jumpsuit — which was layered over a form-fitting bodysuit and sculpting bandeau — unzipped.

A$AP was also on the sidelines during Rihanna’s performance and was seen filming his girlfriend and singing along.

February 15, 2023: Rihanna and A$AP Rocky appear on the cover of British Vogue

The couple, along with their son, posed for the cover of British Vogue‘s March 2023 issue. In the accompanying article, Rihanna shared that having a baby together has only brought her and A$AP closer.

“We’re best friends with a baby,” the “Diamonds” singer said. “We have to be on the same page, but we’ve always kind of had that in our relationship. Everything changes when you have a baby but I wouldn’t say it’s done anything but made us closer.”

February 20, 2023: A$AP Rocky and Rihanna celebrate her 35th birthday

The couple, along with a few family and friends, celebrated the “Umbrella” singer’s birthday with a private dinner at Giorgio Baldi in Santa Monica, California. A source told PEOPLE that Rihanna and her guests had the entire restaurant to themselves.

“Rihanna looked gorgeous and was in the best mood,” the insider said, adding that the pop star and A$AP “were very affectionate” throughout the evening.

May 1, 2023: A$AP Rocky and Rihanna attend the Met Gala

Per tradition, A$AP and Rihanna were two of the last people to walk the red carpet at the Met Gala. The “Diamonds” singer showed off her growing baby bump in a white, spaghetti-strap dress by Valentino, which she paired with a floral cape and Karl Lagerfeld-inspired white gloves.

As for the “Fashion Killa” rapper, he wore a kilt over a pair of denim, a crisp white dress shirt and a black suit jacket.

July 20, 2023: A$AP Rocky teases possible collaboration with Rihanna

Whether it’s music or merchandise, A$AP is “always down to collab” with Rihanna.

“She’s a phenomenal creative. Yeah, there’s a lot of things we’re going to collaborate on, from products for children, there’s a lot of things to look forward to,” he told Complex.

August 2023: A$AP Rocky and Rihanna welcome their second baby

In August 2023, sources confirmed to PEOPLE that Rihanna and A$AP Rocky had welcomed their second child together, son Riot Rose Mayers. He was born on Aug. 1.

“Rihanna feels her family is now complete,” an insider told PEOPLE. “It’s something she’s always wanted.”

September 19, 2023: Rihanna and A$AP Rocky share first photos of Riot Rose

The proud parents released adorable pictures of their family of four in September. It was the first time Rihanna and A$AP shared photos of Riot.

In the snaps, Rihanna held baby Riot while Rocky carried RZA on his shoulders. In other photos, the couple played with Riot as he lay on a blanket.

December 19, 2023: Rihanna says it’s a “turn on” to see A$AP Rocky with their children

According to Rihanna, Riot and RZA are “obsessed” with their dad.

“I love him differently as a dad. It’s a turn on,” she told Page Six, adding that Rocky is a “great, patient, loving” father.

February 22, 2024: Rihanna and A$AP Rocky leave Venice after celebrating her birthday

The couple was photographed leaving Venice after celebrating Rihanna’s 36th birthday. In the pictures, Rihanna and Rocky huddle together under an umbrella, smiling and holding hands.

Earlier in their trip, the pair were seen enjoying a romantic boat ride on the Grand Canal, where they were photographed kissing and laughing.

February 28, 2024: Rihanna and A$AP Rocky debut short film for their first beauty collaboration

To promote their first Fenty collab, a lip balm called Fenty Skin Lux Balm, Rihanna and Rocky costarred in an almost two-minute long short film called Born to Steal: Yours, Mine, Ours.

In the video, Rihanna plays a woman who steals from her lover, Rocky, who is in turn determined to find the thief.