As Aaliyah once sang, “If at first you don’t succeed, dust yourself off and try again.” Those words appear to be the mantra some celebs decided to double down on before spinning their block and taking a second chance at a happily ever after with their ex. As most of us probably know, the decision can be a risky one. But lucky for these celebs, things panned out in their favor. Now, The Shade Room is running down the list of 4 celebrity couples who decided to spin the block for their fairytale ending.
Celebrity Couples Who Spun The Block For Their Happy Every After: Ashanti & Nelly
According to PEOPLE, Ashanti and Nelly initially crossed paths at a press conference for the announcement of the 2003 Grammy Award nominations. Per the outlet, in VH1’s ‘Behind the Music,’ Ashanti explained that Nelly asked her for her autograph.
“The first time I met Nelly, he asked me for my autograph, but I think he was being sarcastic… For the record, it took him a long time to get my number,” she reportedly said on the show.
Fast-forward to February 2006, PEOPLE notes that the pair were seen together at multiple industry events. However, they never explicitly confirmed their romance, and by 2013, rumors swirled that the pair had split.
“It’s a very small industry. Are we gonna see each other? Yeah… I’m not bitter.I feel like in a relationship, it’s like ping-pong. Sometimes you love them, sometimes you hate them. That’s a real statement, everyone goes through that,” she reportedly said when asked about the rapper while sitting down with Angie Martinez in 2014.
Fast forward to September 2021, and all eyes were on Ashanti and Nelly as they both took the stage at Ja Rule and Fat Joe’s Verzuz. To fans’ surprise — and Ashanti’s – the pair shared a huge onstage.
“Now look, this is the crazy part: I had no idea he was gonna be there. I haven’t seen him or spoken to him since we broke up. Six years or something? So, I didn’t know what to expect,” she reportedly said while livestreaming with Ja Rule, per PEOPLE.
#3
Ryan Destiny & Keith Powers
According to Bombshell by Bleu, Ryan Destiny, and Keith Powers met in 2015 at a Teen Vogue party. Per the outlet, during a 2018 appearance on ‘The Real,’ Powers explained that he approached Destiny and asked her how she was doing. From there, he and Powers became friends and ultimately built their chemistry.
#4
In 2019, the outlet notes that Destiny and Powers went public with their relationship.
“For a minute, we tried to hide it for numerous reasons, but as human beings, sometimes you want to just shout to the world, ‘I love this person and I’m happy!’ We try to find a balance. I’m already a private person and very career driven, so reminding people that I am my own person is important,” Destiny reportedly told We The Urban that year, per PEOPLE.
#5
By 2022, however, PEOPLE reports that the pair went their separate ways. At the time, a “source” shared a statement with the outlet:
“They’re taking time to focus on themselves and their emerging careers, but are remaining close friends.”
#6
In February 2025, Destiny exclusively confirmed to PEOPLE that she and Powers are now back on.
“I just love him so much, and I just appreciate him every step of the way,” she told the outlet about her bae. “He’s such a cheerleader for me, as I am for him. It just means everything. We’re just best friends — you know, we’re more than best friends.”
#8
Sterling K. Brown & Ryan Michelle Bathe
According to ELLE, Brown and Bathe met as freshmen in College.
“I saw his audition for ‘Joe Turner’s Come and Gone’ [as an undergraduate at Stanford University]. And I was riveted. I had never seen anybody so young do what he was doing. I was floored. And that’s my first memory of Sterling,” Bathe told The Parade in 2021.
#9
At that time, the pair reportedly started dating but reportedly broke up after graduating from college in 1998.
“We broke up for three and a half years before we came back into each other’s lives,” Brown said while appearing on ‘The Talk’ in 2017, per PEOPLE. “She was on the treadmill working out, and I had this epiphany, ‘I have to go tell this woman she’s the love of my life.’ I go to her apartment, I tell her, and she’s like, ‘Well, I’m working out right now,’ and I was like, ‘No, I can see that— I’ll just talk to you while you’re on the treadmill,’ and she said, ‘Well, I feel like going outside. So I’m gonna go on a run.’ So I’m like, dressed [in a suit], and she starts running through Koreatown, and I start running along with her. Brother had to work, but it was well-worth while.”
#10
The couple reportedly eloped in 2006, per ELLE. To date, the pair shares two children.
#12
Gabrielle Union & Dwyane Wade
According to PEOPLE, Gabrielle Union and Dwyane Wade met in February 2007 at a Super Bowl party.
“I stayed on one side of the room with my people. We like to party and he doesn’t drink at all. He was on the other side of the room holding bible study,” Union reportedly told Essence of their meeting, per the outlet.
Furthermore, at the time, Union was recently divorced from NFL player Chris Howard. Meanwhile, Wade was married to Siohvaughn Funches.
“When I met Dwyane, his résumé looked like crap: athlete, going through a divorce, nine years younger than me. None of that screamed, ‘Let’s have a lasting relationship,'” she recalled to Glamour years later.
#13
Fast-forward to 2010, the pair went public after dating for about a year. In July of that year, Union and Wade posed for photos at the Summer Groove Benefit Dinner in Hollywood, Florida. Additionally, PEOPLE notes that around the same time, the pair were spotted courtside packing on some PDA.
#14
Then, in January 2013, Gabrielle Union and Dwyane Wade split. According to the outlet, in 2014, Union opened up about their decision and the brief period to Glamour.
“When Dwyane and I broke up briefly in 2013, it was because of distance and scheduling. I finished filming [‘Being Mary Jane’], then I flew to Vegas right away to start shooting ‘Think Like a Man Too.’ I couldn’t take time off, and I missed some quality togetherness we desperately needed… Moving forward, I decided my work schedule has to make sense for our family,” the actor explained.
#15
However, by December of that year, Union and Wade were back on and had announced their engagement.
“She said YES!!! @gabunion” Wade wrote via photo shared on Instagram at the time.
#17
Per PEOPLE, Union later shared that Wade incorporated his children into his proposal to her.
“They were like, ‘We wanna do a presentation for you.’ They like to do skits and songs and stuff, so we turn around, and they’re like, ‘Okay, we’re ready!’ and I turned back around and all the boys were holding up signs that said, ‘Will you marry us?'” she said while on ‘Good Morning America.’
#18
By August 2014, the pair were married, per PEOPLE. The pair reportedly tied the knot in an intimate ceremony in Miami.
#20
In November 2018, Union and Wade welcomed a daughter whom they named Kaavia James.
#22
As of August 2024, the pair has celebrated ten years of marriage, sharing a blended family of five children total.
