Whether you’ve seen every episode of their reality shows or you have trouble keeping their names straight, chances are you’ve heard your fair share of news about the Kardashian-Jenner family in the past decade. It’s probably safe to say they’re America’s most famous family.
Why are they always popping up in the headlines? It doesn’t hurt that they’re all beautiful, and they’ve had dramatic love lives, many of which have involved other famous people.
Take a look back at the notable people who’ve had romantic relationships with members of the Kardashian-Jenner family over the years. While there have been plenty of rumored partners we haven’t included, that’s just because we’re sticking with the relationships that were confirmed to have happened.
Arguably the most obvious person to have been romantically linked to the Kardashian-Jenner clan is rapper Kanye West, who has been married to Kim Kardashian since 2014. The pair started dating in 2012 and their union has been a magnet for media attention ever since. One of their most infamous moments of bliss came in 2013, when Kardashian appeared in the music video for West’s song “Bound 2,” which was loaded with moments that seemed too intimate to be on YouTube for all to see! The couple already has three children together and recently announced they are expecting a fourth baby.
The family’s supermodel sister, Kendall Jenner, has been quieter about her dating life than many of her siblings. But that doesn’t mean she hasn’t been publicly linked to several famous suitors. One of those was rapper A$AP Rocky, who had a relationship with Jenner that lasted about a year. The pair started dating in 2016 and later went to the 2017 Met Gala — always a haunt of the famous family — together. They eventually split, apparently because their busy schedules were too incompatible.
A staple of E!’s “Keeping Up with the Kardashians” in the early seasons, former NBA great Lamar Odom was married to Khloe Kardashian for seven years. The couple met in 2009 and tied the knot just weeks after they’d started dating, which was the first hill in this roller-coaster romance. Kardashian and Odom eventually agreed to divorce in 2015, but it was put on hold when Odom was hospitalized after a series of medical episodes. He recovered fully, but the pair officially called it quits in December 2016.
Another famous person who had a dramatic, up-and-down relationship with a member of the Kardashian-Jenners was model Blac Chyna. In 2016, she began dating Rob Kardashian and the two had a daughter together that year. Shortly after the birth of their baby, Dream, the couple split up. Things got ugly between them in 2017 when Chyna filed for a temporary restraining order against Kardashian after he posted personal images of her online. As of 2019, they are reportedly again on speaking terms.
One of the stars of “Keeping Up with the Kardashians” since the first season in 2007, Scott Disick was in a relationship with Kourtney Kardashian from 2006 until 2015. The pair dated, with varying degrees of seriousness, that entire time, all while an audience of millions watched their drama unfold. Kardashian and Disick have three children together but never tied the knot in all those years together. They finally split after Kardashian got tired of dealing with Disick’s selfish and self-destructive behavior, according to reports.
Rapper Travis Scott is one of the most recent people to join the Kardashian-Jenner family. The “Sicko Mode” rapper has been dating Kylie Jenner since 2017. The youngest child of the family gave birth to her and Scott’s daughter, Stormi, in 2018. The first, blurry image of Stormi, posted by Kylie Jenner shortly after her birth, became the most-liked image in Instagram history shortly after it went live. Scott and Jenner were still dating as of February 2019.
Not long after her split from ex-husband Lamar Odom was made official, Khloe Kardashian was rumored to be in a relationship with current NBA star Tristan Thompson. Kardashian, who is seven years older than Thompson, announced she was pregnant with his child in December 2017. She gave birth to daughter True, her first child, in March 2018. The relationship between Kardashian and Thompson was fraught until they broke up in February 2019, with multiple reports of him cheating on her making news during their time together.
Speaking of young NBA stars dating members of America’s unofficial royal family, Philadelphia 76ers point guard Ben Simmons and Kendall Jenner have been together since summer 2018. The pair’s relationship hasn’t exactly been tabloid fodder, but they’ve been spotted together many times in that span, including on Valentine’s Day 2019 in New York City.
Another pro baller who became a legitimate part of the Kardashian-Jenner family was Kris Humphries. The affable athlete was infamously married to Kim Kardashian for just 72 days before the reality star requested a split. The pair had begun dating in 2010 and their entire romance — and rocky marriage — was documented on “Keeping Up with the Kardashians.” Humphries and Kardashian were involved in a lengthy legal battle before their divorce was finally made official in 2013. The ex-NBA player has since said he is certain Kardashian was cheating on him with Kanye West during their relationship.
The youngest of the four Kardashians, Rob, also had a high-profile relationship that ended in a painful way. Rob dated singer Adrienne Bailon (now Houghton) of 3LW and The Cheetah Girls fame, from 2007 t0 2009. Their relationship was shown on “Keeping Up with the Kardashians” in the early seasons. They eventually split up and Rob later admitted it was because he had cheated on Bailon.
It’s sometimes easy to forget about Brody Jenner (son of Caitlyn Jenner and ex-wife Linda Thompson) when you’re looking at the dating history of his massive, famous family, but he’s also dated a few notable women in the past. One of those was Lauren Conrad, with whom Jenner appeared in the MTV reality series “The Hills.” The pair dated briefly in 2007 and Conrad has since said that the show’s producers edited the series in a way that made their relationship look like it lasted longer than it really did. Jenner and Conrad are expected to reunite as part of a reboot of “The Hills” in 2019.
Did you know that the Jacksons and Kardashians were once linked? For a few years starting in the late-’90s, Kourtney Kardashian dated Taryll Jackson, the son of Jackson 5 member Tito Jackson. The couple was reportedly linked when they were both in their 20s, dating from 1999 until about 2004. It’s unclear why they split up, but the timing of the breakup meant Jackson just missed out on being a star in “Keeping Up with the Kardashians.”
Kris Jenner, the matriarch of the Kardashian-Jenner family, was married to attorney Robert Kardashian from 1978 to 1991, then to Olympian Caitlyn Jenner from 1991 to 2015. Since her highly publicized split from the latter, Jenner has been dating Corey Gamble, a man who works in the entertainment business. Jenner is 25 years older than Gamble and rumors of them being close to marriage have been swirling.
Talk about an it-couple for today’s world. Kendall Jenner has been romantically linked with musician Harry Styles several times going back to 2013. Dating rumors first flew that Christmas, when the two celebs were spotted spending time together on a yacht in St. Barts. The pair eventually split up but were seen again on a date in 2016, igniting new rumors. In 2017, it was reported that Styles had written several songs as a nod to his time with Jenner on his debut solo record.
Most people know about Kim Kardashian’s failed marriage to Kris Humphries — but most people don’t realize that was actually her second marriage. When Kim was just 19 years old, she married music producer Damon Thomas, who is 10 years older than her. The union lasted from 2000 until 2004 and court documents eventually showed that Kardashian claimed she was abused by Thomas during their time together.
This was one of the more controversial relationships any member of this famous family has had. After splitting up with fiancee Blac Chyna — who we’ve seen elsewhere on this list — in 2014, rapper Tyga was revealed to be dating Kylie Jenner. The only problem with that? Jenner was just a kid at the time, reportedly only 16 years old when she started seeing Tyga, who was 25 at the time. The pair continued to date for a few years, eventually calling it quits in 2017.
As you’ve seen, Kendall Jenner has had some very famous boyfriends over the years, allegedly including Justin Bieber. The Canadian pop idol has been a friend of the family for some time, but he was romantically linked to Jenner for a few months from 2014 to 2015. The relationship between the two was reportedly never anything serious, but if they had ended up getting married, their combined social media powers could have legitimately broken the internet.
Obviously, Rob Kardashian has had his fair share of notable relationships. One of those was with singer Rita Ora. Kardashian announced he was dating Ora in 2012 after online rumors said they were in a relationship. The pairing didn’t last long, however, with Ora and Kardashian splitting up by the end of that same year. Kardashian quickly tweeted some hurtful things about Ora in 2013, but apparently tried to patch things up with his ex in 2018 over social media.
As we’ve seen with the Kardashian-Jenner family, age differences are no big thing when it comes to finding potential lovers. Such was the case when Kendall Jenner was reported to be seen on several dates with actor Orlando Bloom in 2015. Bloom is nearly 20 years older than Kendall. The relationship was never publicly confirmed by either celeb and it doesn’t appear to have been anything more than a fling if it happened.
Before her marriage to Kris Humphries, Kim Kardashian had a pretty serious relationship with ex-NFL running back Reggie Bush. The pair had a high-profile relationship from 2007 to 2010 and were rumored to be close to getting engaged before it came to an end. After they broke up, it was reported that Kim left Bush because he wasn’t ready to get married. She ended up marrying Humphries in 2011 after a quick courtship.
After Kourtney Kardashian finally walked away from her up-and-down relationship with Scott Disick, her most serious boyfriend so far has been with model Younes Bendjima. Kourtney, who is nearly 15 years older than Bendjima, dated him from 2016 until 2018. Months after their split, Bendjima posted a nice tribute about Kourtney on social media, calling her “a beautiful woman inside and out.”
Rapper and model Romeo Miller, aka Lil Romeo, apparently had a relationship with Khloe Kardashian at a tender time in his life. In 2018, Miller claimed that he had briefly dated Khloe in 2007 when he was a senior in high school and she was in her early 20s. Miller said the relationship was cut short because his father, rapper Master P, didn’t approve and told him to dump her. Khloe herself hasn’t commented on the alleged romance.
One of Kendall Jenner’s more high-profile relationships was with NBA star Blake Griffin. Kendall dated the Detroit Pistons player from 2017 to 2018 before they split and she moved on to fellow baller Ben Simmons. After the breakup, tabloids were abuzz whenever Kendall and Griffin were spotted in the same location together, especially at a Coachella party in 2018, where they were reportedly avoiding each other at all costs, despite being in the same room.
Before Kim Kardashian’s doomed marriage to Damon Thomas had ended in 2004, she was already romantically linked to musician Ray J, the brother of R&B star Brandi. This relationship spawned the infamous sex tape that went public in 2007, launching Kim Kardashian into household name status. The couple had reportedly made the tape in 2003. Kim and Ray J dated until 2006 before calling it quits.
Ah, the more innocent days of puppy love in the Kardashian-Jenner family! When Kylie Jenner was just 15 years old, she had a cute relationship with fellow teen star Jaden Smith, who was 14 years old. The young love wasn’t meant to last, as Smith and Kylie were linked for about a year, wrapping up before she got involved with Tyga. Linking up the Smith family with the Kardashian-Jenners may have been too much star power to handle.
Another NBA player who spent time dating Khloe Kardashian was former North Carolina Tar Heels great Rashad McCants. The pair dated for a brief time in 2009, but McCants has claimed that the relationship had a big impact on his basketball career. McCants’s pro career only lasted a few years, despite heavy expectations coming into the NBA, and he has said it’s because of his time with Khloe. He’s said the media attention that came with being involved in the famous family made the media question how serious he was about basketball.
Another cast member of MTV’s “Laguna Beach” that Brody Jenner dated was Kristin Cavallari (now Cutler). The pair actually dated when Cavallari was 18 years old, following the end of the hit reality series. Their relationship apparently didn’t last long but producers of the sequel series, “The Hills,” urged the pair to carry on a fake relationship for the benefit of the show. Cavallari has said that all of the dating you see between Jenner and herself on “The Hills” was just for entertainment.
Caitlyn Jenner isn’t going to be outdone by her famous family members when it comes to starting a relationship despite a big age gap. The former Olympian has been linked to model Sophia Hutchins for several years, despite an age difference of nearly 50 years between them. Caitlyn and Hutchins reportedly live together but it’s been reported that their relationship is strictly platonic and is more of a friendship than a romantic one. Regardless, Jenner has referred to Hutchins as her “partner.”
Dating Khloe Kardashian — or any member of this family, for that matter — apparently comes at a great cost. Just ask Houston Rockets star James Harden. Harden and Khloe were publicly linked in 2015, and it didn’t go well for the NBA player. He’s since called that period the worst in his life and has said the constant media attention that came with dating her distracted him and made the relationship untenable.
It’s hard to believe that when Kim Kardashian dated Nick Cannon, he was definitely the bigger star in the relationship. The pair saw each other for a few months, starting in fall 2006 and ending in early 2007. Years after they split, Cannon revealed he broke up with her because she lied to him about the existence of her infamous sex tape with Ray J. Despite that lie, Cannon has continued to praise Kim for being nice and for her business acumen.