Odd Celebrity Couples You Forgot Existed
To many of us normies, famous people exist in a vacuum that doesn't expand beyond our phones and our TV screens, where they're perfectly molded for our consumption in every way. Our collective fascination for the rich and famous has no bounds, especially when it seems like there are endless combinations of their relationships with each other. There is just something so interesting that happens when two celebs that seemingly have it all come together — especially when they appear to be from completely different worlds.
Nevertheless, some celebrity unions have been ... odd to say the least. From couples with huge age gaps to bizarre love matches, the random romances on this list will leave you wondering: What on earth did these two people have in common? How is it possible that they dated? And better yet, how does no one remember that this peculiar pairing was even a thing? Let's dive right into the oddest celebrity couples you probably forgot existed.
Chelsea Handler and 50 Cent
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 seemingly spotted on several dates in 2010 that had the media hot on their tails. However, when asked about the relationship, 50 told E! News (via MTV News) that the two were merely meeting up to discuss a film project, and stated, "No, I'm not dating her." Still, 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?"
Over the years, the two stars have kept the details of their romance quite private. When asked about the fling, the "Chelsea Lately" host told Oprah, "It was fun. It wasn't the most serious relationship." In 2013, 50 seemed to echo this sentiment, choosing his reputation over admitting if he was ever in love with the comedian on "The Howard Stern Show" (via MTV News). The rapper also cited issues with his ex-girlfriend Ciara as the reason for their split during his chat with the shock jock.
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." Regardless, the two seem amicable. The rapper even publicly denounced the former president when Handler jokingly suggested she'd rekindle their fling if he did so.
Nicole Kidman and Lenny Kravitz
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. While renting his apartment, the outlet reported that Kidman grew closer and closer to the rocker. She also bonded with his daughter, Zoë Kravitz, years before the two women would star alongside each other on "Big Little Lies". The secretive couple even got engaged but called it off before any nuptials were made.
"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," Kidman shared with Vanity Fair in 2007. "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 to Mr. Porter in 2017 that he had remained friends with his unlikely former lover, stating, "Nicole is amazing." They were snapped looking friendly together just a year earlier at the Hollywood Film Awards.
Russell Brand and Katy Perry
In 2010, pop sensation Katy Perry and comedian Russell Brand got engaged after just four months of dating. The curious couple tied the knot with a luxurious traditional Indian wedding that featured everything from elephants to safari trips for guests. Three months later, rumors emerged that the couple was already struggling and receiving marriage counseling — gossip that Perry denied, per the Daily Mail. However, by the end of 2011, the two were done. Speaking to Vogue two years later, the singer alleged that Brand had informed her of his plans to divorce her via text message on New Years Eve. She also raised her suspicions that Brand was threatened by her success and couldn't handle the dynamics of their marriage.
In 2020, Perry, who now shares a child with boyfriend Orlando Bloom, sat down with "60 Minutes Australia" to reflect on her early-twenties marriage. "I met someone that was interesting and stimulating," she said about her ex-husband. "It was just like a tornado, it was everything happening at once." Over time, Brand has gone from bitterness to affection when speaking of his ex-wife and their relationship. In the documentary, "BRAND: A Second Coming" (via People) he recalled, "I [was] living ... this life of the very thing I detest: vapid, vacuous celebrity." Years later, he changed his tune about Perry, and told UKTV, "I still feel very warm towards her. When I hear about her or see her, I think 'Aww, there's that person.';"
Harry Styles and Taylor Swift
In 2012, at the height of One Direction's powers and hot on the heels of the success of "Red," Harry Styles and Taylor Swift briefly dated. Naturally, the relationship incited some furious responses from fans, but nevertheless, the couple persevered for two months. The couple eventually broke up after reportedly having a heated argument while on vacation in Virgin Gorda. Unresolved feelings lingered in their music. Swift's "Out of the Woods" and "Style" were rumored to be about the 1D star, and she's coyly confirmed "I Knew You Were Trouble" was about Styles as well. As for the "Watermelon Sugar" star, his co-written 1D track "Perfect" was rumored to be about her.
Since the breakup, both parties have been timid about discussing what went down. While Swift has thrown some subtle shade, Styles has mostly avoided the topic altogether. On the rare occasions when he did speak about Swift he was always nice. On an episode of "The Howard Stern Show," the performer took the time to praise Swift's songwriting abilities when asked about exes writing songs about him. "I think about what it means to me to write a song about somebody else and for somebody else to do that, it's like flattering, even if the song isn't that flattering," he said. "... Ultimately, using Taylor as an example, she's a great songwriter." Interestingly, the pair were spotted catching up at the 2021 Grammy's and seemed to be on friendly terms.
Ashley Olsen and Lance Armstrong
Former child star Ashley Olsen and disgraced 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. However, if Juliet Macur's tell-all about Armstrong's infamous fall from grace, "Cycle Of Lies: The Fall of Lance Armstrong" (via Radar) is to be believed, their age gap is what drove this duo apart.
The book alleged that Armstrong was advised against dating Olsen by his handlers as the relationship was considered a threat to his reputation. Most notably, John Koioth, the head of Armstrong's Livestrong Foundation, warned that the fling could affect his charity work and requested that the former cycling champ end the romance. According to Macur, Armstrong allegedly responded, "She's twenty-one... F**k 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
Madonna and Dennis Rodman's relationship is by far one of the strangest on this list. According to the rainbow-haired basketball star's autobiography, "I Should Be Dead By Now," the two dated for roughly six months back in the '90s. He added that he was hardly infatuated with the pop superstar when she first started calling up the Spurs' office asking for him. "I didn't like her music," he wrote. "... [I] didn't like anything about her." However, he soon realized that Madonna was more than her media persona, and she was actually pretty cool. Despite her alleged desire to marry him, he wasn't interested. "If I had married Madonna, my career would have come second," he wrote, "Madonna was like a f***ing industry. She was General Motors."
Rodman has spoken candidly about the relationship many times. In an interview with "The Breakfast Club," he even claimed that the performer was so desperate to get pregnant by him that she offered $20 million to have his baby. Madonna hasn't commented on the claims or the relationship, as a whole. However, Rodman has suggested that the two remain friends to this day. Despite all 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."
Bella Thorne and Scott Disick
In 2017, rumors of a romance between Bella Thorne and Scott Disick were running rampant. The two had been spotted enjoying a casual dinner date and were seen hopping on a flight from LAX together just a week later. Gossip regarding the two was heightened when paparazzi caught the pair looking cozy together on a daybed in Cannes, France.
Speaking to Complex, Thorne suggested that the two met when Disick showed up at one of her house parties with French Montana. While they had fun, it seems like the pair were just not a match. The former Disney star told the outlet that she couldn't keep up with the renowned socialite's partying. "Scott is really nice, sweet, charming," she said. "I don't drink, and he really drinks a lot. And it just ended up ... I just wasn't down. I was like, 'I gotta leave.'" She elaborated that the two were only in Cannes for a day and a half before she left due to Disick's alleged hardcore partying. "I was like, 'Woah, this is not the way I live my life, bruh,'" she added.
On "The Jenny McCarthy Show," Thorne later clarified that her relationship with Disick was never sexual, insisting that they were just friends. By the same token, Kendall Jenner alleged in "Keeping Up With The Kardashians" (via Entertainment Tonight) that Disick had very maturely orchestrated the situation to annoy his ex-girlfriend, Kourtney Kardashian.
Pete Davidson and Kate Beckinsale
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 on the smoking patio for an hour. 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. The pair seemed smitten already, with an insider telling the outlet, "Kate thinks [Pete is] the sweetest and nicest guy."
The two were spotted having fun together at hockey games, parties, and while attending a dinner with Beckinsale's parents, and their PDA became the stuff of legend. A source told E! News that the two appeared to share a unique connection built around good vibes and good times. "They may seem like an unlikely match but she thinks he's great and she just loves all the laughs she has with him," they said. After four months of dating, the two eventually split with People reporting that the long-distance element of their relationship had put a strain on the romance. "They're still friendly, but it just didn't work out," another anonymous source told the outlet. Davidson's dance card has been full ever since.
Tom Cruise and Cher
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 the disco legend dated briefly in the '80s, having first met at Madonna and Sean Penn's wedding. Though they didn't actually start dating until much later, Cher admitted to the Daily Mail that there was a vibe between herself and the actor from the get-go.
She was 39 years old at the time, and Cruise was 23. "I was so crazy about him," Cher recalled in an interview with Oprah Winfrey (via People). "He was so wonderful ... He was a shy boy. He didn't have any money." The "Mission: Impossible" actor was just starting his career at the time, while the pop superstar was fresh off the heels of a divorce from songwriter Sonny Bono. Cher seemed to be attracted to his everyday boy-ish charm and of course, 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. "He wasn't a Scientologist then," she reminisced to Andy Cohen on the show (via PageSix). "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."
Channing Tatum and Jessie J
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 even happened. The two were first spotted together in October 2018, a few months after Tatum split from long-time wife Jenna Dewan and they soon began showing up to each other's shows. Tatum attended the Wiltern Theater with his 5-year-old daughter in tow to cheer on his new girlfriend, while Jessie attended the opening night of "Magic Mike Live" in London. Around the same time, Tatum appeared to make the relationship Instagram official by posting a tribute to his girlfriend's performance prowess 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 if they had desires to have children, with Jessie laughing 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.
Ariana Grande and Nathan Sykes
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, with the "7 Rings" singer telling 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."
The duet that she's referring to is "Almost Is Never Enough", a romantic ballad that was featured on the "Mortal Instruments: City of Bones" soundtrack. As Grande told the outlet, 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 the Twitterverse by storm. They had no choice but to confirm their romance in a series of sugary, affectionate tweets (via Seventeen).
Sadly, the couple called it quits a few months later due to their busy schedules. However, they remained close, even collaborating on a track for Sykes' album in 2016. Funnily enough, 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 be bothered by that at all. He told TMZ that he was relieved not to be featured and that he couldn't think of anything he learned from his relationship with the singer either. "It's been a long time," he remarked.
Brooke Shields and Michael Jackson
This one's a major throwback! In the 1980s, Brooke Shields and King of Pop Michael Jackson were rumored to be dating. However, Shields tells a different story. "Of course we loved each other, but nothing happened romantically," she told People. Just teens when they met, the pair clicked instantly and became inseparable with the actor explaining that the two young stars felt safe with each other and shared a deep connection. "Together, we felt impervious to the craziness that swirled around us," she explained. Shields further suggested 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 everlasting, with Shields going on to share her respects at Jackson's memorial in 2009. Shortly after Jackson's sudden death, Shields contributed to the commemorative issue of Rolling Stone dedicated to the late singer. In the emotional issue, Shields revealed that the singer had proposed to her several times, and lamented on what she would respond each time he asked. "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,'" Shields told the outlet. "I think it made him relax. He didn't want to lose things that meant something to him."
Justin Timberlake and Fergie
Back in the late 90s, singers Justin Timberlake and Fergie engaged in an extremely age-inappropriate relationship, making them one of the weirdest couplings on this list. Fergie revealed to Australia's Courier-Mail (via Pop Sugar) that they allegedly started dating when Timblerlake was 16 and Fergie was 23, a little while before Timberlake's infamous relationship with Britney Spears. The "Big Girls Don't Cry" singer went into more detail about the coupling with Cosmopolitan. "One of my good friends was dating J.C. Chasez, and so we'd all hang out with 'N Sync. Justin and I would go out together and have fun and make out," Fergie shared. "We went to Hawaii together, but we were never serious. He was Mr. Right Now."
While she was initially open about discussing the relationship, it seems that with time, Fergie might've realized just how improper it was that she was involved with a minor in her early twenties. During a 2017 appearance "Watch What Happens Live!" with Andy Cohen, the singer smartly avoided the question when the relationship was brought up. "It wasn't all that serious. Am I allowed to pass on this? Pass. Plead the fifth." Timberlake, on the other hand, has never spoken about the relationship publicly.