Kim Kardashian & Nick Cannon

Before Kim Kardashian became one half of Hollywood’s most powerful duos with Kanye West, she tried her shot at love with Nick Cannon. The couple dated in 2006, a year before Kardashian’s breakout show, “Keeping Up with the Kardashians,” premiered. Though their romance was short-lived, the tabloids continue to use it to dig up drama, like that Cannon’s ex-wife, Mariah Carey, was jealous of his relationship with Kardashian. Cannon later shut that down, saying that Carey didn’t even know who Kardashian was. According to Us Weekly, Cannon and Kardashian broke up over her sex tape with Ray J.

Nick Lachey & Kim Kardashian

After his high-profile divorce from Jessica Simpson, Nick Lachey briefly dated Kim Kardashian in 2006 after they met at a party for their mutual friend Arizona Cardinals quarterback Matt Leinart, according to the Daily Mail. However, the relationship doesn’t seem to have ended on good terms. In an interview with Details, Lachey suggested that Kardashian used his celebrity to become famous by tipping off paparazzi to their dates.

“Let’s just say this: We went to a movie. No one followed us there. Somehow, mysteriously, when we left, there were 30 photographers waiting outside,” he said. “There are certain ways to play this game, and some people play it well.”

Jaden Smith & Kylie Jenner

Jaden Smith and Kylie Jenner both come from famous families, so it’s no surprise that they ended up dating. The twentysomethings, who were family friends growing up, dated from 2013 to 2014. The relationship was so serious that Jenner brought Smith as her date to her sister Kim Kardashian’s wedding to Kanye West in 2014. To keep their high-profile relationship private, Smith was known to resort to stunts with the paparazzi, such as when he put on an Iron Man costume to walk around with his then-girlfriend in New York City.

“She’s one of my best friends. It’s pretty awesome,” Smith told Wonderland magazine of his relationship with Jenner in 2013. 

Cody Simpson & Kylie Jenner

Before Cody Simpson dated Gigi Hadid, he was briefly linked to Kylie Jenner. According to E! News, the two met at the Hollywood premiere of “Breaking Dawn: Part 1” in 2011 when Kylie and her sister, Kendall, interviewed the singer.

“You’re my rumor boyfriend on Twitter,” Kylie told Cody. “Nice to finally meet you.”

“I think Kylie should date Cody Simpson because they’d be so cute together,” Kendall later told the camera.

Though it’s unclear how long the relationship lasted, the two were linked in late 2011 and were spotted together until 2012. In an interview with Ross Mathews, Simpson joked that the relationship ended because he felt pressure to change his name to start with a K. ‘The whole K-O-D-Y thing didn’t really work for me,” Cody said.

Ben Flajnik & Kris Jenner

In 2014, rumors circulated that Kris Jenner was romantically involved with former “Bachelor” Ben Flajnik after the two were photographed on multiple dates, including one double date with Kim Kardashian and Kanye West at the rapper’s concert in Oakland, California. The dates came after Flajnik ended his engagement with his “Bachelor” winner, Courtney Robertson.

Despite the rumors, both Flajnik and Jenner have denied being romantically involved. “Ben and I are good friends,” Jenner told E! News in 2013. “I think he is a great guy, but we aren’t dating!”

Cristiano Ronaldo & Kim Kardashian

In April 2010, an insider for The Sun spotted Kim Kardashian and soccer superstar Cristiano Ronaldo making out at a restaurant in Spain. According to the insider, Kardashian, who was in Spain for a three-day trip, and Ronaldo were enjoying a romantic dinner together before they were seen locking lips later in the night.

“She and Ronaldo were kissing and very affectionate,” the source said. “They looked to be getting on really well, laughing the whole time.”

Though it’s unclear if the two dated or only hooked up, Ronald has since denied being in a relationship with Kardashian, according to HollywoodLife.

Justin Bieber & Kourtney Kardashian

In 2015, several outlets reported that Kourtney Kardashian and Justin Bieber were an item after they were spotted on multiple dates, including one instance in which Kardashian showed up at Bieber’s surprise concert in Los Angeles. The rumors reached an all-time high when Kardashian and Bieber posted Instagrams of each other hanging out. In one picture, the two can be seen visiting Universal’s Hollywood Horror Nights together. In another, Bieber can be seen leaning over an unidentified woman, whom many fans believe was Kardashian. He captioned the Instagram, “Lord knows,” which fans also believe is a jab at Kardashian’s ex-boyfriend, Scott Disick.

Though neither has confirmed nor denied the romance, Bieber spoke highly of the mom of three, whom he claims to have known for a long time, in an interview on The Bert Show. “No, no, but for real, she’s great,” Bieber said. “I’ve known [the family] for years.”

In response to the tabloid coverage of their relationship, Bieber had this to say: “I’m being used, man. What can I say?”

Harry Styles & Kendall Jenner

After months of rumors, Kendall Jenner’s older sister, Khloé Kardashian, confirmed that she dated Harry Styles in an interview with Entertainment Tonight.

“They were hanging out together. Do I think they’re dating? Yes. I don’t know if they’re like boyfriend-girlfriend. Nowadays, I don’t know, people are weird with stuff. So I don’t know their ‘title,'” Kardashian said. “But I mean, they were in St. Barts together hanging out, so to me that’s dating. I would call that dating.”

The two dated briefly in 2016, with rumors reaching an all-time high in June when Kendall was photographed on a yacht with Harry in St. Barts. In September, the couple was spotted at a romantic dinner by an onlooker, who told People that the model “was beaming” on her date.