One of the most renowned singers and famed action star? A comedienne and a
rapper? These couples gave a new whole new meaning to "opposites attract".
Chelsea Handler and rapper 50 Cent engaged in a strange romance that lasted about five
months. Though they feverishly denied the rumors several times, the unlikely duo was spotted on
several occasions in 2010 that had the media hot on their tails. When asked about the relationship,
50 told E! News that the two were merely meeting up to discuss a film project. But
he did hint that he might have a sweet spot for the late-night host, saying:
"Yeah I did send her flowers [after the VMAs] ... why not?"
The two stars have kept the details of their romance private. When asked about the fling,
the Chelsea Lately host told Oprah:
"It was fun. It mean, it wasn't, you know, the most serious relationship,
but he came on my show and he sent me a bunch of flowers."
In 2013, 50 seemed to echo Handler's statement, choosing his reputation over admitting if he was
ever in love with the comedian on The Howard Stern Show. Seven years later, 50 publicly
endorsed Donald Trump on social media, prompting his comedian ex-girlfriend to respond on Twitter:
"You used to be my favorite ex-boyfriend."
The rapper publicly denounced the former president
when Handler jokingly suggested she'd rekindle their fling if he did so.
Few remember that actress Nicole Kidman and musician Lenny Kravitz dated pretty
seriously back in 2003. According to People, while the two claimed to be pals in public,
the couple was apparently inseparable in private and frequently met for secret
rendezvous in Manhattan. The two shared a love for music and the city but also bonded
over their lives as single parents. Kidman also bonded with his daughter, Zoë Kravitz,
years before the two women would star alongside each other on Big Little Lies.
"They ended up on the same show, and Zoe hadn't seen Nicole since she was younger."
The secretive couple even got engaged but called it off before any nuptials
were made. Kidman shared with Vanity Fair in 2007:
​​"I didn't really want a relationship. I just wanted my kids to have me,
and I didn't feel comfortable having some person in that small hubbub. And then I got
engaged to somebody ... but it just wasn't right. I wasn't ready. We weren't ready."
Kidman didn't confirm Kravitz's identity until nearly ten years later,
during an interview with Net-a-Porter. Despite calling off the engagement,
the rocker confirmed in 2017 that he had remained friends with his unlikely former lover, stating,
"Nicole is amazing."
Former child star Ashley Olsen and road racing cyclist Lance Armstrong were first linked
sometime in 2007, when they were seen on a few cozy dates around New York City. The odd union
came shortly after Armstrong ended a year-long relationship with fashion designer Tory Burch.
The 15-year age gap in his new relationship subsequently caused a stir in the tabloids,
but the couple apparently paid the public no mind. According to Juliet
Macur's tell-all book about Armstrong's infamous fall from grace, Cycle Of Lies:
The Fall of Lance Armstrong, their age gap is actually what drove the duo apart.
The book alleged that Armstrong was advised against dating Olsen by his handlers because
the relationship was considered a threat to his reputation and his charity work.
The head of Armstrong's Livestrong Foundation requested that the former
cycling champ end the romance. According to Macur, Armstrong allegedly responded:
"She's twenty-one… F--- you."
In 2008, the couple had seemingly parted ways with
Olsen moving on with Justin Bartha while Armstrong started dating Kate Hudson.
Madonna and Dennis Rodman's relationship is definitely a strange match. According
to Rodman's autobiography, I Should Be Dead By Now, the two dated for roughly
six months back in the '90s. He stated that he was hardly infatuated with the
pop superstar when she first started calling up the Spurs' office asking for him. He revealed:
"I didn't like her music [...] [I] didn't like anything about her."
He soon realized that Madonna was more than her media persona and that he actually enjoyed
her company. Despite her alleged desire to marry him, he wasn't interested. He wrote:
"If I had married Madonna, my career would have come second. Madonna was
like a f---ing industry. She was General Motors."
In an interview with The Breakfast Club, Rodman even claimed that the performer was
so desperate to get pregnant by him that she offered $20 million to have his baby.
"Were you disappointed that y'all, that you didn't get her pregnant?”
“No. Well…well.’
Madonna hasn't commented on the claims or the relationship, but Rodman has suggested that
the two remain friends to this day. Despite the drama, it seems like the
relationship was pretty casual. In 2019, Rodman downplayed it completely telling USA Today:
"We had a nice little fling. We came together in
the perfect time. She was stagnating in her career, and I was coming up."
Three months after his split from Ariana Grande, Pete Davidson was spotted getting
close to English actor Kate Beckinsale. According to E! News, the two first met at a
2019 Golden Globes after-party, where a source claimed they were seen flirting for an hour.
"Apparently, apparently people have a crazy fascination with
our age difference. Uh, but it doesn't really bother us."
The odd couple was then spotted publicly for the first time leaving the Los Angeles comedy venue
Largo at the Coronet, where they held hands as paparazzi snapped pics. An insider told E!News:
"Kate thinks [Pete is] the sweetest and nicest guy."
The two were spotted having fun together at hockey games and parties. While attending a dinner with
Beckinsale's parents, their PDA became the stuff of legend. A source told E! News:
"They may seem like an unlikely match but she thinks he's great
and she just loves all the laughs she has with him."
After four months of dating, the two eventually split according to People,
reporting that the long-distance element of their relationship had
put a strain on the romance. An anonymous source told People:
"They're still friendly, but it just didn't work out."
Musical icon Cher's love life has featured a number of high-profile relationships,
but surprisingly one of her most lowkey was with megastar Tom Cruise. The Top Gun star
and disco legend dated briefly in the '80s, having first met at Madonna and
Sean Penn's wedding. Though they didn't start dating until later,
Cher admitted to the Daily Mail that there was a vibe between them from the get-go.
She was 39 years old at the time,
and Cruise was 23. Cher recalled in an interview with Oprah Winfrey:
"I was so crazy about him. He was so wonderful. He was a shy boy. He didn't have any money."
Cruise was just starting his career at the time,
while the pop superstar had already been married and divorced twice. Cher seemed
to be attracted to his everyday boy-ish charm and Cruise went along for the ride.
Though the couple eventually separated, it seems they remained on good terms.
In a 2013 episode of Watch What Happens Live!, Cher seemed happy to talk about
her ex and revealed that the actor was in her top five of all-time best lovers.
"Where did Tom Cruise rank on that list?”
“Well he was in the top five."
She reminisced by saying:
"He wasn't a Scientologist then. It was pretty hot and heavy for a little minute.
He's a great guy. The person that I knew was a great and lovable guy."
British singer Jessie J and actor Channing Tatum dated on and off for two years before
splitting up for good in 2020. The relationship wasn't super private, but for some reason, most
people completely forgot it ever happened. The two were first spotted together in October 2018,
a few months after Tatum split from long-time wife Jenna Dewan. Tatum attended the Wiltern Theater
with his 5-year-old daughter to cheer on his new girlfriend, while Jessie attended the opening
night of Magic Mike Live in London. Tatum appeared to make the relationship Instagram official by
posting a tribute to his girlfriend's performance following her show at the Royal Albert Hall.
By June of 2019, the couple was already being asked if they wanted to get married
or had desires to have children. Jessie laughed off the speculation
during an interview with Heart Breakfast. In December, they split up for the first
time but reunited in time for the new year. The couple then did their first red carpet
together in January 2020 but were broken up for good by April. Six months later,
Jessie seemingly confirmed the split in an Instagram post she cryptically captioned,
"Single life in a pandemic is ... " alongside a mysterious crystal-ball emoji.
In 2013, Nathan Sykes of The Wanted and pop superstar Ariana
Grande engaged in a PDA-filled fling. The couple first met on a red carpet,
long before they collaborated on a duet. Grande told Entertainment Wise:
"We locked eyes with each other all night. I thought,
he was cute as hell. Nothing happened obviously and then, the duet came about."
Their duet, "Almost Is Never Enough", is a romantic ballad that was featured on the Mortal
Instruments: City of Bones soundtrack. Grande told the outlet that the couple shot an intimate
video for the single but didn't really connect until they met again on Justin Bieber's tour. By
September, the rumors surrounding Grande and Sykes had taken Twitter by storm. They had no choice but
to confirm their romance in a series of sugary, affectionate tweets, according to Seventeen.
But the couple called it quits a few months later due to their busy schedules. They remained close,
even collaborating on a track for Sykes' album in 2016. The boy band member is the
only one of Grande's exes that wasn't featured on "Thank U Next" — but he
doesn't seem to mind. He told TMZ that he was relieved not to be featured, saying,
"It's been a long time."
In the 1980s, Brooke Shields and King of Pop Michael Jackson were rumored
to be dating. But Shields tells a different story. She told People:
"Of course we loved each other, but nothing happened romantically."
Just teens when they met, the pair clicked instantly and became inseparable. Shields
explained that the two young stars felt safe with each other and shared a deep connection. She said:
"Together, we felt impervious to the craziness that swirled around us."
But Shields revealed to Rolling Stone that as they got older,
Jackson maintained his innocence surrounding sexuality and romance.
Though they didn't work out romantically, their bond was
unique and lasted until Jackson's passing in 2009. Shortly after Jackson's sudden death,
Shields contributed to the commemorative issue of Rolling Stone dedicated to the
late singer. Shields revealed that the singer had proposed to her several times. She wrote:
"I would say, 'You have me for the rest of your life, you don't need to marry me, I'm going to go
on and do my own life and have my own marriage and my own kids, and you'll always have me."