ASAP Rocky Spills The Most Difficult Things He Had To Do In Order To Woo Rihanna While Courting Her

Today, we’ve got some juicy details about ASAP Rocky and his alleged difficulties in courting the music industry’s queen, Rihanna. Stick around to find out what went down! Before we dive into the nitty-gritty of ASAP Rocky’s courting challenges, let’s take a quick look at the timeline of their relationship. Rumors of their romance started swirling in 2016, but it wasn’t until 2019 that they made their official debut as a couple. The world couldn’t get enough of this power couple, but it turns out, things weren’t as smooth as they seemed. According to reports, ASAP Rocky allegedly revealed that it was no walk in the park trying to make Rihanna accept him. So, what exactly did ASAP Rocky say about his courting struggles?

ihanna and A$AP Rocky are in the club of power couples who will inevitably go down in history. The longtime friends made their romance official in 2020, after months of dating rumors and years of being at each other’s side.

Below, we track how their relationship blossomed from friendship to romance—and now, to parenthood. Here’s everything to know so far.

February 20, 2024: The couple “love[s] being parents.”

A source for Entertainment Tonight offers some insight into the duo’s new life as parents of not one but two little boys.

“Rihanna and A$AP are doing so well,” the insider says. “They both love being parents and balance each other out. A$AP is very outgoing and playful, and Rihanna is chill and fun.”

The source adds, “They make each other laugh and are also interested in the same things, like music, fashion, business ideas, art, and more, so they have fun together no matter what they’re doing.”

December 19, 2023: Rihanna is happy to be a “boy mom.”

During an interview with Entertainment Tonight, the superstar opens up about raising sons RZA and Riot with Rocky.

“They’re the best, though. Having a house full of boys—I thought I was a girl mom, but I’m a boy mom. I love this. I love it,” she says.

As for how RZA is adjusting to life as a big brother, she says, “He struggled in the beginning, but he loves his little brother. Every time he thinks we’re not looking at him, he’ll come over and touch him. If the baby’s crying, he’ll just hold his hands. It hurts him if the baby’s crying. He’ll wake up in the morning just saying, ‘Baby, baby, baby.’ He loves him. It took a while, but he got there, and I’m proud of him.”

August 2023: Rihanna gives birth to baby number two.

TMZ reports the couple welcomed their second child together sometime in August, with Rihanna giving birth in a Los Angeles hospital. While the baby’s name and gender have yet to be revealed, the outlet notes that the new addition’s name begins with the letter R.

“Rihanna feels her family is now complete,” a source tells People. “It’s something she’s always wanted.”

June 21, 2023: Rocky fuels marriage rumors with Rihanna.

While performing for Spotify Beach at the Cannes Lions International Festival of Creativity in France, the rapper seems to drop a major hint about his and Rihanna’s relationship status.

Rihanna supports her man during the show, dancing along and watching his performance from a balcony. She wears a black see-through Jean Paul Gaultier bodysuit with diamond paneling and a halter neckline, plus a sparkling sequined bikini from Oséree underneath.

A witness at the set tells Entertainment Tonight that before Rocky performed “D.M.B.”—the title of the ode to Rihanna stands for “dat’s my bitch”—he dedicated the song to “my beautiful wife in the motherfucking building! I love her.”

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The two previously sparked marriage speculation in the music video for “D.M.B.” There, Rihanna makes multiple PDA-filled appearances and shows up at the end as a bride dressed in red. During the wedding in the video, Rocky wears gold grills that spell out MARRY ME? while Rihanna wears her own bedazzled grills that read I DO.

February 15, 2023: Rihanna gushes about raising a family with Rocky.

In an interview with British Vogue, Rihanna discusses her relationship with her life partner and shares insight into how they’ve adapted to parenthood.

“We’re best friends with a baby,” she 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.”

She said that seeing Rocky become a dad to their baby son has been incredibly special, and she cannot get enough of their close bond. “Their connection is undeniable. The second Rocky makes eye contact with him he is on fire,” she said, adding of their son, “He is obsessed with his father. And I’m like: ‘Didn’t I give birth to you? What is going on?'”

February 12, 2023: Rocky cheers on Rihanna after she announces that she’s pregnant with baby No. 2!

A rep confirmed to The Hollywood Reporter and People that the singer is expecting her second baby. She made the announcement at the beginning of her explosive Super Bowl Halftime performance, in which she descended onto the stage while rubbing her growing baby bump.

In a video shared by the NFL’s Instagram account, Rocky adorably cheers her on from the sidelines. He can be seen recording her performance with his phone and bopping along to the music.

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February 10, 2023: Rocky supports Rihanna ahead of her Super Bowl performance.

An Entertainment Tonight insider reports that Rocky has been Rihanna’s rock throughout her months-long preparation for her much awaited performance at this Sunday’s Super Bowl Halftime Show.

“A$AP has been very supportive throughout her preparation and has really been stepping up his parenting game while she has been busy with rehearsals,” a source tells the outlet. “[A$AP] and her son plan to be there supporting her during her big day.”

The insider adds that Rihanna has been working hard to ensure that the upcoming show, which marks her first live performance in six years, does not disappoint.

“Rihanna has been preparing for her Super Bowl LVII halftime show for months and wants it to be the most iconic performance,” the source continues. “She really kicked things into gear and got right to work after she received the call. She has been nonstop in the studio, in design meetings, and working out to make sure she is fully prepared. Rihanna has been very hands on with every detail throughout the entire process. It is super exciting for her to get back out there and perform since having her son and she feels rejuvenated after taking some time off.”

May 2022: Rihanna is already a “wonderful mom.”

A source close to the couple tells People that the new parents are doing well at home in Los Angeles with their baby, whom Rihanna and Rocky welcomed earlier in the month. “They are very excited to be parents,” the insider says. “Rihanna is already a wonderful mom.”

May 13, 2022: Rihanna gives birth.

The couple welcome the arrival of their first child, a baby boy, per TMZ on May 19.

March 2022: The couple had a secret baby shower.

Rihanna and A$AP Rocky throw a “rave-themed” baby shower for their little one on the way, Entertainment Tonight reports. “They flew out some family and friends from Barbados,” a source tells the outlet.

“Rihanna has a great sense of humor and loves to have fun,” the insider adds.

Also per ET, HipHollywood receives exclusive details on the party, including its neon-themed attire, as well as its hilarious party favors: T-shirts printed with Rihanna’s and Rocky’s faces.

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February 2022: Rihanna and Rocky are excited about parenthood.

Following the news that Rihanna and Rocky are expecting, an exclusive People source tells the outlet that the singer has been welcoming her new pregnancy with open arms. “She couldn’t be happier and is so excited to be a mom,” the source said. “She’s loving all the changes to her body during pregnancy and has always celebrated pregnant women in her runway shows for Fenty.”

The source also affirms that the singer is confident in her decision to embark on parenthood with Rocky and has never felt obligated to rush the process. “Having a baby is something she was never focused on, but being with Rocky opened her up to the idea,” the source added. “Everything Rihanna does, she does it her own way on her own time table, and having a baby is no different.”

The insider continues, “They’re just like any other pair of parents-to-be. Yes, they happen to be famous but they’re just the cutest, giddiest young couple that’s expecting kids.”

“Everyone is happy it’s all working out,” another source tells the outlet. “They will be great parents.”

January 2022: Rihanna and Rocky share the news that they’re expecting.

Rihanna is pregnant with her and A$AP Rocky’s first child.

The singer debuts her baby bump in a series of photos taken around Harlem in New York City. She pairs a hot pink vintage Chanel puffer coat with ripped jeans, as well as body jewelry adorned around her stomach. Rocky opts for a denim Carhartt jacket, knit hoodie, and black leather trousers.

August 2021: Rihanna and Rocky are in it for the long haul.

According to People, Rihanna and A$AP Rocky do not have any plans to slow down their romance. “They are crazy about each other,” a source tells the outlet.

“This romance evolved since they were friends first. They already knew and respected each other and it has just grown from there,” another source reveals.

“They loved to laugh and have a blast together before they even dated,” the source continues. “All of that makes for a solid romance now.”

May 19, 2021: A$AP Rocky discloses his feelings for Rihanna.

Rocky leaves no confusion in the air during an interview with GQ: He and Rihanna are a serious item, and he is absolutely smitten with her.

In addition to calling Rihanna both “my lady” and “the love of my life,” the “PMW” rapper reveals that the two rented a tour bus last summer and embarked on a “Great American Road Trip,” which had a significant hand in strengthening their bond. “I met myself,” he says of the trip. “Being able to drive and do a tour without feeling like it was an occupation or an obligated job agreement, I feel like that experience is like none other,” Rocky recalled. “I never experienced nothing like it.”

A$AP Rocky acknowledges his past as a shameless ladies’ man. But upon being asked what it’s like to be in a relationship, he responds, “So much better when you got the One. She amounts to probably, like, a million of the other ones. I think when you know, you know. She’s the One.” Cue the waterworks.

April 12, 2021: Rihanna and A$AP Rocky go on a dinner date at Delilah in Los Angeles.

The two indulge the paparazzi with a public rendezvous at Delilah in Los Angeles. Both are spotted leaving the restaurant wearing matching leather ensembles—he in a simple black leather jacket and pants, she in a brown vintage leather fur coat from Archive.

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The pair have been reportedly inseparable since last summer. Although Rocky has been infatuated with Rihanna for years, they went official in the summer of 2020, according to a source. “Things changed over the summer and they finally hooked up. They’ve been together ever since,” the insider told Us Weekly.

January 2021: Rihanna publicly supports A$AP Rocky’s footwear in an Instagram photo.

On Instagram, Rihanna wears a metallic bikini and cover-up skirt, in addition to strappy heels designed by Rocky himself in collaboration with footwear designer Amina Muaddi: the Amina Muaddi x AWGE LSD Gladi Thigh Heel.

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“New year’s resolution: apply the pressure,” she captioned the image. This simple gesture testifies to Rihanna’s continuing public support of her man.

Late December 2020: Rihanna and A$AP Rocky show some PDA in Barbados.

A$AP Rocky and Rihanna are continuing their Barbados Christmas getaway. The singer is spotted getting cozy with her new beau atop a yacht for a beach-bound date, wearing a sexy emerald-green slipdress and sporting her signature mullet for the occasion.

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A source reveals to Entertainment Tonight that due to their longstanding friendship, which existed before the pair decided to become romantic, a trip back to Barbados to meet Rihanna’s family was bound to happen.

“They’ve known each other for so long as friends and in a work setting, which makes it so easy for them to get along, travel together and be involved in each other’s lives to the full extent,” a source tells ET. “They always have such a good time together and definitely seem in love.”

December 24, 2020: Rihanna and A$AP Rocky take a Christmas Eve cruise in Barbados.

A$AP Rocky joins Rihanna and her family in Barbados for the holidays, during which the couple take a romantic “Catamaran sunset cruise” on Christmas Eve.

A source tells People, “Rihanna has been in Barbados since [last] Thursday. … A$AP joined her and they are spending Christmas together with Rihanna’s family.”

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December 9, 2020: Rihanna and A$AP Rocky are reportedly “inseparable.”

A People source reveals just how happy Rihanna is with her new beau. “They’ve been inseparable the past few weeks,” the insider says. “It’s a new relationship, but they both seem very into it.”

Though Rihanna’s last relationship with Saudi billionaire Hassan Jameel allegedly ended due to their different lifestyles, no such conflict seems to exist between Rihanna and Rocky. “They’ve always seemed to have a great time together,” added the source. “They have a lot in common. … They both are very much about helping out in the communities where they grew up.”

Rihanna and Rocky have yet to acknowledge the dating rumors publicly, but the source relays that Rihanna is all in. “Rihanna seems very happy dating A$AP.”

December 2, 2020: Rihanna and A$AP Rocky take a winter night walk together.

Despite how Rihanna and Rocky have both remained tight-lipped about ongoing dating rumors, the duo are spotted one evening strolling around New York City together. Per paparazzi photos published at TMZ, both are seen bundled up in winter puff jackets and face masks.

December 2020: Reports allege that the two have made their relationship official.

Page Six reports that Rihanna and Rocky have finally taken their relationship to the next level after the pair are spotted at the Beatrice Inn in New York City. People reports at the time that a source has confirmed the romance.

August 26, 2020: The two collaborate on Fenty Skin.

In videos shot for Vogue and GQ, Rihanna recruits Rocky to talk all things skin care, just in time for the launch of her Fenty Skin line.

“Men love their skin, and they take care of it, but they feel obligated almost to only use products that are for men because anything beyond that feels too feminine, it’s not for them, they’re not allowed, they don’t have permission,” Rihanna told her friend in the video.

Rocky also gets candid about his skin care routine. “I had to discover face cleansing and skin care all at the same time when I was a young buck in the shower,” he says in the video. “You can’t wash your body with the same rag you wash your face with. I was lucky enough to be the type of guy that wants to wash my face.”

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Rihanna Asks A$AP Rocky 18 Questions | GQ

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Rocky is also featured in promo shots for the new line, for which he poses alongside Rihanna.

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January 2020: Rumors that Rihanna and Rocky are an item begin to swirl.

Rumors that Rihanna was linked to A$AP Rocky begin to swirl after sources report that the Fenty Beauty founder had split from Hassan Jameel, her boyfriend of three years.

“[Rihanna and Rocky] shared a hotel suite during that trip in New York,” a source tells The Sun at the time, adding, “Rihanna is reluctant to put a label on it as it’s so soon after Hassan. They’re really enjoying each other’s company and taking things easy as it’s still early days.”

The insider continues, “It’s really casual between them and she’s not thinking about whether there’s a future with Rocky. She’s a newly-single girl having fun.”

December 2, 2019: They attend the Fashion Awards in London.

The two friends walk the red carpet together at the British Fashion Awards.

Rihanna wears a mint-green satin dress by her fashion brand, Fenty, and accessorizes with a matching wrap, gloves, and heels. She tops off the look with a diamond choker necklace. Meanwhile, Rocky supports the singer’s fashion endeavors in a black suit by Fenty.

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Rihanna and A$AP Rocky pose at the British Fashion Awards.

September 12, 2019: Rocky again attends Rihanna’s Diamond Ball.

The rapper attends Rihanna’s annual Diamond Ball for a second consecutive year.

September 13, 2018: Rihanna invites Rocky to her annual Diamond Ball.

Rihanna’s Diamond Ball doubles as the fashion affair of the year and a charitable event, as it supports funds to the Clara Lionel Foundation, the organization she founded to support educational programs across the globe.

Rocky makes his debut at the fourth annual Diamond Ball, for which he wore a sleek black suit and diamond stud earrings.

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A$AP Rocky, Diamond Ball

June 21, 2018: The two attend a Louis Vuitton show together.

The duo sit together front row at the Louis Vuitton show during Paris Fashion Week, demonstrating how closely they’ve maintained their friendship over the years.

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Rihanna and Rocky attend the Louis Vuitton menswear spring/summer 2018 show as part of Paris Fashion Week.

2013: Rocky joins Rihanna’s tour.

The rapper joins the North American leg of Rihanna’s Diamonds World Tour, performing as her opening act.

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A$AP Rocky performs in concert at Air Canada Centre on March 18, 2013, in Toronto, Canada.

2012: Rocky and Rihanna collaborate together.

Rocky is featured in a remix of Rihanna’s single “Cockiness (Love It),” a song about the singer’s sexual dominance over her partner. It includes suggestive lyrics, like, “I can be your dominatrix / Just submit to my every order / Enter my diamond matrix / Devour my golden flower.”

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Rihanna – Cockiness (Love It) (Remix) (Audio) ft. A$AP ROCKY

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After the song’s release, the duo performed together at the MTV Video Music Awards.

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[HD 1080p] Rihanna ft A$AP Rocky & Calvin Harris – Cockiness & We Found Love Live at the VMAS