The Kardashian-Jenner family is a big group of socialities, and so it’s no surprise that among them they have many ex-partners from all walks of the celebrity life. It includes models, rappers, athletes, actors, and more. American’s unofficial royal family sure gets around. Something all these exes share is the claim that they’re been affected by the Kardashian curse. Let’s dive in and see if there’s any evidence of that at all, why don’t we?
Ray J is the one that helped catapult the family to fame. This American rapper and actor featured alongside Kim in her infamous 2003 tape. He was actually the one accused of leaking it, for publicity. Ray J’s real name is William Ray Norwood Jr, and he’s the brother of the more famous singer Brandy, plus he’s cousins with Snoop Dogg. Ray J and Kim got together when he was 22 and she was 23.
Ray J Today
The rapper and Kardashian had been broken up for an entire year before the tape was leaked.
The man himself eventually followed in the footsteps of the Kardashians with his own reality TV show called For The Love Of Ray J in 2009 and then in a follow-up reality TV show alongside his sister Brandy. He later married co-star Princess Love, but the marriage only lasted 4 years, with Love filing for divorce in 2020.
Tyga And Kylie Jenner
This pairing caused quite a stir due to the big age gap between Jenner and the singer. This was especially so at the beginning of the relationship. They got together in 2011 when Jenner was only 14 years only, and Tyga was 21.
Although nothing was official, there was obvious flirting, until Tyga eventually canceled his engagement to Blac Chyna and officially started dating Kylie. They swear they were just friends up until that point.
Tyga Today
The two of them planned on getting married eventually, but alas it wasn’t meant to be. Jenner even got Tyga’s name tattooed on her ankle, but luckily it was possible to have it redone so it said “LA” instead.
No one is sure why they broke up, but Hulk Hogan of all people got embroiled in a beef with him, which lead to accusations that he cheated on Jenner. What a crazy situation to see.
Adrienne Bailon And Rob Kardashian
The only Kardashian brother dated the singer and actress Adrienne Bailon for a mere two years, during the period of 2007 to 2009. At the time Balion was in the Disney-funded band The Cheetah Girls, and another band called 3LW.
She even featured on the Kardashian’s main TV show but eventually dumped Rob after he was unfaithful. She maintains that being involved with the family was a mistake. She wanted a complete break from them.
Adrienne Bailon Today
Since 2013 Balion has been a co-host on the daily talk show The Real, alongside another teen star named Tamera Mowry. Her role in the show actually made her the first Latina daytime show host in the United States.
Some of her other appearances include competing in The Masked Singer. For a time she was engaged to music industry exec Lenny Santiago, but they split up in 2015. She married singer Israel Houghton in 2016.
Lamar Odom And Khloé Kardashian
Following what has been described as a whirlwind romance, Khole Kardashian married basketball superstar Lamar Odom. The two met back in 2009 at a party thrown by the Lakers and were married a short year later.
He featured prominently on the family’s show, leading to the couple getting their own spin-off. Unfortunately, Odom suffered from substance abuse issues, and Kardashian had him admitted for treatment in 2015. They were very nearly divorced back in 2013.
Lamar Odom Today
Eventually, Kardashian and Odom did get divorced. Following a long recovery, Odom released a book in 2019 about his struggles. In it he admits that he was unfaithful to Khloe and that he even used to threaten her while drunk.
Today he is engaged to fitness instructor Sabrina Parr. He even has a tattoo of her name. They’re often spotted stepping out in Los Angles. He and Khloe are still on good terms these days.
PartyNextDoor And Kylie Jenner
Most of the Jenner-Kardashian relationships have their off periods, and in those moments another partner may step in for a little while. During one such break from Tyga, Kylie took the opportunity to have some fun with PartyNextDoor.
She even starred in one of his music videos. When quizzed about the relationship, Kylie Jenner said that she had never gotten to do the couples stage thing before and that she had a lot of fun.
PartyNextDoor Today
PartyNextDoor whose real name is Jahron Anthony Brathwaite continues to be a popular rapper. He was the first to sign up with Drake’s record label and has even performed with him and other big acts like Big Sean.
Interestingly enough, it was he who wrote Rihanna’s hit “Work”. Since Jenner, PartyNextDoor has stayed single, but before Jenner, he was with the RnB singer Kelani. Some fans speculate that one of his songs is about this.
Scott Disick And Kourtney Kardashian
It’s hard to know where to begin with this one. Scott Disick is considered by many to be an honorary Kardashian. He and Kourtney were already together when the family’s show began airing in 2007.
The show documented much of their relationship, including the births of their three children—Mason Dash, Reign Aston, and Penelope Scotland. Scott Disick was known for his outrageous behavior and went to rehab many times. The two split up in 2015.
Scott Disick Today
Despite a very troubled relationship, Disick and Kardashian continue to co-parent their children and often spend time together that’s amicable. They’re often seen on vacation together and Scott maintains a relationship with the rest of the family.
In 2017 Disick started dating Lionel Richie’s youngest daughter, with an age difference of 15 years. This drew some outrage. The couple decided to go more lowkey after that, but they are still spotted out in public together.
Nick Lachey And Kim Kardashian
You’ve probably heard of this singer from the band 98 Degrees from his troubled marriage and the accompanying TV show, with Jessica Simpson. You might also remember him from the show Love is Blind, which he hosted.
Either way, Lachey once went on a date with Kim K back in 2006. In an interview with Andy Cohen, he said it’s incorrect to say they’re exes. They just went to watch The Da Vinci Code together.
Nick Lachey Today
Lachey claims that Kim called some paparazzi during their date, because they were met by 30 photographers as they left the theatre. Today he is married to Vanessa Minnillo, whom he met while shooting the music video for “What’s Left of Me”.
The two got engaged in 2011, and now they have three kids together named Camden John, Brooklyn Elisabeth, and Phoenix Roberts. It seems like celebs really like long and strange names for kids.
French Montana And Khloé Kardashian
After the end of her marriage to Lamar Odom, Khloe got together with the Moroccan-American rapper French Montana. This was in 2014. The couple’s relationship lasted less than a year. While it didn’t work out, they have remained on friendly terms with one another.
In an interview, Montana says they had a great relationship, but it wasn’t meant to be. This is certainly a rarer instance of two high flyers falling out but staying friends.
French Montana Today
French Montana, whose real name is Karim Kharbouch, and Kardashians still keep in touch, and he even features on the family’s shows from time to time. He even attended Khole’s 40h birthday, following his scandalized relationship with Tristan Thompson.
Montana was granted US citizenship in 2018 and released a third album in 2019. He is known for collecting exotic pets like Tigers, and he even has a cute baby monkey that he’s named Julius Caesar.
Blake Griffin And Kendall Jenner
For a very brief period between 2017 and 2018, Jenner dated the LA Clippers player Blake Griffin. As she’s generally quite private, Jenner kept the details out of the papers, but this relationship actually ended Griffin’s engagement to his long-time partner Brynn Cameron.
In court papers, Brynn Cameron states that Blake Griffin cared more about celebrities than his own family and his responsibility as a father. It’s actually a pretty sad outcome all things considered.
Blake Griffin Today
The two’s relationship ended when Griffin was drafted to play for the Detroit Pistons and he had to move across the country. During the 2019 to 2020 season, he had to undergo knee surgery and so he missed the first ten games.
It’s unclear when he’ll be able to resume play. Since his split with Jenner, he’s been spotted with multiple other women, including Tinashe and Brooke Fletcher, who reports for Fox News Sports Division.
Rashad McCants And Khloé Kardashian
In case you haven’t realized it yet, there are a lot of basketball players on this list. In 2008 Khloe got with the former basketball player Rashad McCants after the pair were introduced by NFL player Reggie Bush.
At that point, Bush was dating Khloe’s sister Kim, which made the pairing easier. He features in one episode of the family’s show, as the relationship only lasted seven months. Many of these relationships are pretty short.
Rashad McCants Today
Like many on this list, Rashad McCants implied that his involvement with the Kardashians had a negative effect on his career.
In an interview in 2017, he was quoted as saying that if he hadn’t gotten with her, he would have been a player worth about $70 million today. It’s alleged Khloe left him because he cheated, and during the break up he missed some work and eventually went to play in foreign leagues overseas.
Cody Simpson And Kylie Jenner
Back in 2011 when they were both still teenagers, Kylie Jenner and Ozzie popstar Cody Simpson dated. It wasn’t a very serious relationship, but by all accounts, they made a good pairing.
It was during this time that Kylie would be introduced to a future boyfriend, Jaden Smith. Smith in turn would eventually introduce Jenner to Jordyn Woods, who for a time would be her best friend. Much came out of this very short relationship.
Cody Simpson Today
Kylie Jenner would by no means be the last celebrity that Cody Simpson dated. He went on to date many others, such as Gigi Hadid for two years, in the period of 2013 to 2015, and later he got together with ex-Disney star Miley Cyrus.
Following that, he experimented with stage acting and landed a role on Broadway as a leading man. He also had a great run on Australia’s version of The Masked Singer.
Jaden Smith And Kylie Jenner
Here’s a fun fact. Jada and Will Smith named each of their kids with a longer version of their own names. Will becomes Willow and Jada becomes Jaden. There’s that celebrity kid naming thing again.
After dating Cody Simpson, Jenner would get with Jaden Smith. The two dated for about a year in 2013, and although they split, they stayed on good terms with one another. Their relationship was highly publicized indeed, but ultimately short-lived.
Jaden Smith Today
Drama alert! Remember how we said that Jaden Smith introduced Kylie to her best friend Jordyn Woods? Well, when Khloe was dating Tristan Thompson, he cheated on her with Jordyn! That’s a real spicy one. The Smith family backed Jordyn, which created a strain on the Smith-Jenner relationship.
As for Jaden, he’s been living the life of a celebrity kid, getting into conspiracy theories, and shooting a Netflix cartoon about pink-haired exorcists. Yes, that’s real.
Nick Cannon And Kim Kardashian
Before Kim Kardashian was really big, she dated the comedian, actor, and rapper, Nick Cannon. The two dated for one year, and there are many photos of them sporting kitschy mid-2000s fashion. At that time, Kim was working as Paris Hilton’s assistant.
The two split up when Kim’s infamous tape was finally leaked. While Kim Kardashian accused Ray J, however, Cannon suspects it might have actually been Kim who leaked it. Would that surprise you?
Nick Cannon Today
Nick Cannon could honestly have his own list and it would be about as big as this one. The Short Circuits creator married Mariah Carey in 2008, but unfortunately, they have since divorced.
They have twin daughters together, plus he has another child, a son, from the well-known supermodel Brittany Bell. His son was born just a year after his divorce. Nick Cannon has recently been in hot water over political comments made during interviews.
Joe Francis And Kourtney Kardashian
Here’s one that the Kardashians probably wish they could forget. Hollywood is no stranger to sleaze. For a time Kourtney dated Joe Francis, who was well known for his show, Girls Gone Wild.
This show preyed on young intoxicated girls at parties and got them to reveal themselves. The Kardashian sisters have actually posed for some of his productions, and he introduced Scott Disick to the family. We suppose some good came out of it.
Joe Francis Today
It may not surprise you to learn that Joe Francis has a number of legal issues. He was convicted of tax evasion, bribery, assault, attempting to interfere with a witness, and false imprisonment.
Worst of all, he pleaded no contest to charges relating to child abuse. In 2003, Francis spent a total of 339 days in jail, and he was later sentenced to 70 days more, plus three years of probation, and anger management therapy.
Rita Ora And Rob Kardashian
Time for another Rob feature. In 2012 the one Kardashian man dated the British singer Rita Ora. The two of them were together for years… Just kidding it was a couple of months and they kept it lowkey.
After they split, the singer said that it was just a fling, while Kardashian said that she cheated on him with over 20 other men. He then took to Twitter to roast her to his many fans.
Rita Ora Today
Rita Ora certainly didn’t need the Kardashians to get any fame, she was already established before them. The singer, who was born in Kosovo, released a second album in 2018, and a single called Let Me Love You made her the first to see 13 Top 10s in the United Kingdom.
She briefly dated Calvin Harris, Ricky Hilfiger, and Andrew Garfield in 2018. She certainly didn’t suffer from the dreaded Kardashian curse, now did she?
Jordan Clarkson And Kendall Jenner
As we’ve said, the Jenner-Kardashian family date many athletes. Jordan Clarkson is no exception. He played for teams such as the LA Lakers, and the Cleveland Cavaliers, which might as well be dating pools for the famous sisters.
The two were seen at Coachella, and Kendall attended most of Jordan’s games when he was playing for the Lakers. Clarkson previously dated Chanel Iman, so he clearly likes models, while Jenner likes basketball players. Perfect match.
Jordan Clarkson Today
When his relationship with Jenner was through, Clarkson was traded over to the Cavaliers in 2018, and then over to the Utah Jazz in 2019. There were a number of rumors in 2018 that Jenner’s good friend Bella Hadid was with Clarkson, but on Twitter, Hadid dismissed it all as gossip.
Today Clarkson is partnered up with Ally Russell, the ex of fellow basketballer Lonzo Ball. What a web of celeb relationships to dig through.
Kris Humphries And Kim Kardashian
Kim Kardashian has had three marriages so far. The second one was to the basketballer, Kris Humphries. Avid viewers of the family’s TV show began to pick up that something wasn’t right with their relationship, but Kardashian still wanted to go through with the marriage.
The two began their relationship in 2010 and were married not even a year later in 2011. Their wedding was a royal affair, and got a two-episode deal on E!
Kris Humphries Today
As you may know, the marriage was a disaster and only lasted for a span of 72 days, or about two months. The collapse was all caught on tape when Kim admitted she didn’t love her husband.
The entire divorce process lasted way longer than the marriage did. By the time it was settled, Kardashian had already started dating Kayne West. Many accused the couple of faking the relationship and marriage for views on E!
A$AP Rocky And Kendall Jenner
As we’ve said, the Jenner-Kardashian crew isn’t limited to basketball or football players. They also date a lot of rappers. In 2016, A$AP Rocky and Kendall Jenner got together and even went to the Met Gala as a couple.
Like so many other relationships on this list, the two split up in about a year, because their schedules conflicted too much for it to work. That said the split was amicable on both sides.
A$AP Rocky Today
We suspect A$AP Rocky may have been hit with the Kardashian curse, The rapper has gotten into numerous fistfights, which have ended in him often being arrested and jailed.
The last straw was in Sweden, where he was formally charged with assault and detained for a month in a Swedish prison, with then-president Donal Trump calling for his release. We must say, reading all of this it appears he had quite a “Rocky” time.
Younes Bendjima And Kourtney Kardashian
After a decade spent with Scott Disick, Kourtney Kardashian got together with Younes Bendjima, who is an Algerian model. The two met during a troubling trip to Paris, during which Kim was taken hostage and robbed.
All of them were there for the Paris Fashion Week and were together when the invasion occurred. Much like Scott’s new girlfriend, Younes is 15 years younger than Kourtney. The two had a brief relationship that ended in 2018.
Younes Bendjima Today
The Algerian model was apparently quite controlling of Kourtney, and he constantly shamed her and attacked her for posting revealing swimsuit photos on Instagram. Despite the relationship ending, the two have been somewhat friendly.
Bendhima, Drake, and Odell Beckham Jr. were all sued by a guy who claimed they attacked him outside of a nightclub in West Hollywood. Funnily enough, before Kourtney, he dated Disick’s current girlfriend, Lionel Richie’s youngest daughter. An appropriate age pairing.
Blac Chyna And Rob Kardashian
Here’s another case of a relationship crossover. Blac Chyna is the ex of Tyga, whom he left for the underage Jenner sister. Chyna had crossed paths with the Kardashians many times and ended up becoming good friends with Kayne West’s ex, Amber Rose.
Then she got together with the Kardashian’s brother Rob, before announcing their engagement. The two aimed to get married in about 2017, with the engagement in 2016. What a lot to track.
Blac Chyna Today
Rob and Chyna, whose real name is Angela Renée White, had a child, named Dream Renée Kardashian in the same year they got together, but then they split the year they were supposed to marry.
They had a short-lived reality TV spinoff, but it all came tumbling down following some nasty rumors about leaked nude photos, and sex videos. Chyna ended up getting a restraining order. What an ending. The Kardashian curse bites both ways.
Damon Thomas And Kim Kardashian
Most people know about Kim’s disastrous marriage to Kris Humphries, and everyone knows about her marriage to Kayne West, but how many people know about her first marriage to Damon Thomas?
Kardashian and the music producer eloped when Kim was just 19 years old. She admits it wasn’t a good idea. Thomas was actually the one who ended things three years later. Kardashian would later reveal that Damon Thomas abused her throughout the three-year marriage.
Damon Thomas Today
After their divorce papers were leaked, Damon Thomas would deny the allegations that he abused Kim Kardashian. He, as do so many of the exes on this list, accused Kim Kardashian of wanting publicity.
According to him, she cheated on him and was obsessed with becoming a celebrity. She on the other hand says that he got her to quit college and have plastic surgery. Damon Thomas would later have a child with Sarai Torres.
Justin Bieber And Kourtney Kardashian
Here’s a bizarre pairing. Justin Bieber has been known to associate with the Jenner sisters, but it appears he also got together with the elder sister Kourtney after she broke up with Scott Disick.
Throughout 2015, Bieber and Kardashian were seen together in public many times, before Bieber got together with Hailey Baldwin. When asked about the relationship, Bieber casually denied everything. A likely story, but we think the evidence all certainly speaks for itself.
Justin Bieber Today
We’re sure we don’t need to tell you Bieber is doing well today, but let’s recap. Bieber had an intermittent relationship with Selena Gomez from 2010 to 2018. The popstar also managed to cultivate an intermittent relationship with Hailey Baldwin.
Sometimes he went back and forth between the pair. He finally settled on Baldwin, and the two were married in 2019 at a ceremony in Carolina. It’s speculated they may have had a civil union.
James Harden And Khloé Kardashian
Khloe is certainly the least fortunate of the Jenner-Kardashian clan when it comes to relationships. She’s had a bad run, and that includes her time with James Harden.
Khloe met Harden at one of Kayne West’s birthday parties. It wasn’t long before he cheated on her. She was later interviewed saying he stressed commitment in the relationship, but then didn’t commit himself. Khloe didn’t take any nonsense and was out of there fast as possible.
James Harden Today
Harden appears to have joined the enemy faction, as he’s been spotted hanging out with the Jenner-Kardashian rival Jordyn Woods. It’s alleged the two are simply friends, however.
In terms of his career, Harden is one of the NBA’s top scorers and an eight-time champion. In the love department, he’s dated Ashanti, Amber Rose, Lesanik, Brittanny Renner, and Pargo. At the moment he is in a relationship with influencer Gail Tiffany Golden, a tech wiz.
Rihanna And Rob Kardashian
You probably forgot all about this one. The Kardashian brother Rob once date Rihanna, the RnB pop queen. It turns out their first date was spent go-karting, and going to the LA Playhouse nightclub.
The two got together after Rob split with Rita Ora, and Rihanna split from Chirs Brown. After Rob, she got back with Chris Brown. Was the relationship with Rob really that bad, RiRi? Chris Brown will feature later on this list.
Rihanna Today
Rihanna is another celeb on this list that doesn’t require us to let anyone know how she’s doing. She’s another celebrity that certainly escaped the Kardashian curse as her career has only been going from strength to strength.
She dated Drake on and off for a couple of years, and then she dated a Saudi businessman named Hassan Jameel for three years, between the years 2017 and 2020. She has many more projects coming up.
Lewis Hamilton And Kendall Jenner
Kendall Jenner is perhaps the most discrete member of the family and keeps her relationships very quiet. She doesn’t often comment on who she is with, or if she’s with anyone at all. We can only speculate and review the evidence for the most part.
That said, there were two instances in which she was spotted with the British racing legend, Lewis Hamiton. She was spotted wearing his chain at one of his racing events.
Lewis Hamilton Today
Lewis Hamilton is one of the biggest racing drivers in the history of the world. He recently announced an intention to retire after a debacle on the track, which saw him losing a race due to some interference.
He has dated Nicole Scherzinger, Rihanna briefly, and even Rita Ora, and Winnie Harlow. He has also been connected to multiple models throughout the years. It seems that he’s hot stuff both on the track and off.
Luka Sabbat And Kourtney Kardashian
Another love interest that has been linked to the Jenner-Kardashian clan is the star of Grown-ish, Luka Sabbat. It appears that Kourtney really likes them young, as the age gap between the two is a whole 20 years.
The two were seen together in 2018, and he’s been known to associate with the wider Kardashian. He was one of the attendees at Kayne West’s Sunday Services at Coachella. Is there anyone the Jenner-Kardashians don’t know?
Luka Sabbat Today
There is no evidence that Sabbat has dated anyone since the alleged time spent with Kourtney. The actor is actually on friendly terms with Kendall Jenner, and the two frequently appear together in group photos with other models.
Sabbat lays claim to the titles of stylist, creative, director, model, and actor. He has a massive Instagram following of over 2 million and has worked with brands like Evian and Calvin Klein. What an auteur indeed.
Travis Scott And Kylie Jenner
The younger Jenner and Travis Scott, an acclaimed rapper, first met when he performed at Coachella in 2017. He was continuing a tour, and Jenner decided that she would accompany him. A mere month later she was pregnant with their daughter, Stormi Webster.
Another strange name. Following accusations of cheating, Scott and Jenner broke up, but maintain friendly relations, and co-parent their daughter as a team. Some rumors suggest the two are actually still together.
Travis Scott Today
Despite the constant rumors that the two are still together, they both maintain that they’ve split up, and are better as friends than as lovers. It’s possible crazed fans just can’t cope with the fact that the two have broken up.
There is evidence to suggest that Scott has been in communication with the female rapper Iggy Azalea, as they often exchange messages on Instagram. He also frequently likes her posts, leading fans to suspect.
Chris Brown And Kendall Jenner
We told you he’d be on this list, and here he is. It’s been alleged that he dated Kendall Jenner for a while. Chris Brown is now infamous for the abuse he subjected Rihanna to, but in spite of that, he still continues to work in the music business.
In 2009, photos of Rihanna’s injuries outraged people the world over. It is said that Brown and Jenner got together twice. Twice in 2014, and 2016.
Chris Brown Today
You know what they say, you can’t keep a bad man down, and Chris Brown just keeps coming up, even though he was charged for beating Rihanna up and threatening her.
He’s been involved in multiple instances of violence since. This includes a fight with Drake, and another with Frank Ocean. He also had a hit and run on his record, plus a charge of brandishing a deadly weapon. The police have also raided him.
Gabriel Aubry And Kim Kardashian
Just before Kim K got with the controversial superstar Kayne West, she got with some of Hollywood’s biggest bachelors. One such man was the model Gabriel Aubry, all the way from up North in Canada.
At that point, he was just out of a long five-year stint with Halle Berry. Kardashian and Aubry were spotted together at a basketball game, and seen together on Thanksgiving, indicating that things were serious. Alas, it wasn’t to be.
Gabriel Aubry Today
Following his split with Halle Berry in 2010, Aubry and Berry went through a tense and upsetting custody battle over their daughter. Berry wanted to take their daughter to France to live with her soon-to-be new husband, Olivier Martinez.
The tension between Aubry and Martinez boiled over and lead to a fistfight. Following this, Gabriel Aubry was hit with a restraining order, meaning he couldn’t be within 100 feet of Halle Berry or his daughter.
Taryll Jackson And Kourtney Kardashian
The Jenner-Kardashians and the Jackson family have been friends for decades, so it isn’t a surprise that there would have been interdating at some point. In the early 2000s, Kourtney dated Tito Jackon’s kid, Tyrell for about four years.
The families would later compete in a charity softball game and were actually featured on an episode of the family’s reality show. Although their relationship eventually ended, the two remained on good terms with one another.
Taryll Jackson Today
These days, Taryll is one of the three members of the pop group 3T. The group is made up of him and his brothers, Toriano and TJ Jackson.
He has also done work as a songwriter for his famous aunt Janet Jackson, as well as for Bruno Mars and Lindsay Lohan. Besides that, he also does work as a solo artist and has also appeared on a reality TV show called The Jacksons: Next Generation.
Ben Simmons And Kendall Jenner
Here we have another ex of a Jenner that is something of a mystery. In fact, he might not be an ex at all. He is also yet another basketball player.
So, no one was surprised when Kendall started dating Ben Simmons in 2018 when they were first seen having lunch in Beverly Hills and then partying it up in Manhattan. Ellen DeGeneres got the scoop when Jenner confirmed they were together on her show.
Ben Simmons Today
Where is Simmons today? Well, he spends most of his time with his team the Philadelphia 76ers, in Phillie, but rumor has it he and Jenner are still together, and he does spend some of the off-season in California and New York, where Jenner splits her time too.
While he hasn’t been with anyone since Jenner, there’s word of him being with Dylan Gonzales. Time will tell if Jenner and Simmons are still a couple.
Tristan Thompson And Khloé Kardashian
Setting aside Kim Kardashian’s extremely brief marriage to Kris Humphries, this might be the most gossip-worthy pairing on this whole list. Khloe’s fans were happy when she got with NBA player Tristan Thompson, but then, when Khloe was a full nine months pregnant, Thompson slept with someone else.
Khloe even forgave him, but then he cheated with close Kardashian family friend Jordyn Woods. You know what they say about fool me once, fool me twice.
Tristan Thompson Today
By some absolute miracle, Khloe and Thompson are still on speaking terms, so that the two can co-parent True Thompson, their daughter. After the massive blowup in 2019, the two separated during a wild media storm.
Today, Thompson lives near Khloe, but we’re not sure how involved he is. He did leave another pregnant woman to get with Khloe in the first place… Rumor has it that Khloe Kardashian is still actually interested in him.
Demi Lovato And Rob Kardashian
In his younger days, it appears that Rob Kardashian was quite a Cassanova. Whether he was hanging out with Rihanna or dating Rita Ora, Rob was certainly getting out and about.
Back in 2010, Rob was seen with former Disney star Demi Lovato. They were bowling, which indicates that Rob likes to keep it light and fun. It’s reported that Rob even took the two little Jenner sisters to watch one of Demi Lovato’s concerts.
Demi Lovato Today
Rob and Demi’s breakup was amicable and they remain on good terms. The former Disney start has since dated a number of other celebrities, such as Wilmer Valderrama, Guilherme Vasconcelos, Henri Alexander, Autin Wilson, and Luke Rockhold.
These days she’s with actor Max Ehrich. Lovato has battled with a number of substance abuse issues and has spent time in rehab programs, but it appears these days that she’s doing quite well. It’s great to see.
T.J. Jackson And Kim Kardashian
Remember how we brought up the Jacksons and their connection to the Kardashians, well the cross-over didn’t end with Kourtney Kardashian and Tyrell. For a period of time, Kim dated TJ.
In fact, they were together during high school and were each other’s first loves. The 3T star said in an interview that the pair dated from the ages of 14 to 18! They even attended prom together. There’s a little-known Kim Kardashian fun fact.
T.J. Jackson Today
Besides performing with his brothers in 3T, TJ has also appeared in a couple of reality TV shows. He is married to Frances Casey, and they’ve been together for many years, since the early 90s!
They have four kids together. The first was born in 1999, another in 2008, another in 2010, and then the last was born in 2015. He is also the sole legal guardian of Michael Jackson’s kids, Paris, Prince, and Blanket.
Orlando Bloom And Kendall Jenner
We have here another unorthodox pairing. It’s another one of Kendall’s low-key affairs, and it’s none other than Lord of the Rings and Pirates of the Caribbean star, Orlando Bloom.
When quizzed, Bloom claimed he didn’t even have Jenner’s phone number, but it’s possible he was a little worried about the scrutiny as 20-year age gap would bring. Orlando Bloom and Kendall Jenner got together following his divorce, but fans were glad it didn’t last.
Orlando Bloom Today
Luckily for everyone, these days Bloom is happily married to someone his own age, and he even has another kid on the way. The actor has a son from his ex-wife Miranda Kerr and will be having a daughter with the pop singer Katy Perry.
Bloom and Perry got involved in 2016, and he popped the question on Valentine’s Day of 2019. It seemed rocky at first, but Bloom is on his way to happiness.
Reggie Bush And Kim Kardashian
The first Kardashian boyfriend to ever appear on the family’s flagship show was Reggie Bush, although the two had a fairly brief relationship, by normal standards, being together from 2007 to 2009. Can you guess what Bush’s profession was?
That’s right, he was a pro ballplayer. The pair met at the ESPN Awards in 2007, introduced by Matt Leithart. At the time, Kardashian and Bush were both in their 20s. They were a popular couple.
Reggie Bush Today
After his relationship with Kim Kardashian, Bush hooked up with singer-songwriter, Jessie James, but he must have a thing for Armenian women because he eventually married Lilit Avagyan. The pair have three kids together.
A daughter named Briseis was born in 2013, a son named Uriah was born in 2015, and then another son by the name of Agyemang, born two years later in 2017. Kim K fans have snidely called Mrs. Bush a lookalike.
Miles Austin And Kim Kardashian
After being dumped by Reggie Bush, Kim went for yet another professional football player. She got together with Miles Austin, a former wide receiver for the Dallas Cowboys.
Kardashian and Miles’ relationship was kept largely under wraps, but Kim insisted that it was serious. They ended up splitting after their professional schedules conflicted. Austin had to pay attention to his football career, while Kim was jet-setting around the world filming her show with the family.
Miles Austin Today
After retiring from the NFL, Miles Austin ended up becoming a coach and scout. He’s done work for the San Franciso 49ers, and his former team, the Cowboys. Keeping on brand, he married a Cowboys cheerleader in 2014, named Stacy Sydlo.
The two have three kids together, named Miles the Fourth, Ava, and Maven. He went back to college where he completed his history degree, in order to set a good example for his kids.
Harry Styles And Kendall Jenner
Here we have a real A-lister and heartthrob, Harry Styles. Back in 2013, he and Kendall were seen together, and they’ve been seen together multiple times since.
As always, Kendall Jenner was cagey about the details, so fans couldn’t know anything for sure. In 2019, the two appeared on The Late Late Show and were more forthcoming, confirming that they were romantically involved, by openly flirting. The two are known to be on and off.
Harry Styles Today
This superstar got his start on X-Factor but has gone so much further. He was one of the most popular members of the boyband One Direction, and since its breakup, he debuted as an actor in Christopher Nolan’s historical war hit, Dunkirk.
He’s also released a second solo album and has begun experimenting with a gender-fluid fashion sense. It’s said that he’s currently back together with his ex, the Victoria’s Secret model, hottie Camille Rowe.
Lil Twist And Kylie Jenner
While all the Jenner-Kardashians have a thing for rappers and pro athletes, Kylie definitely leans more towards the rapper side of the spectrum. After her relationship with sometimes rapper Jaden Smith, she got together with Lil Twist.
Then, following that relationship, she got together with Tyga. Kylie was just 15 years old when she and Lil Twist started dating. At that point, Lil Twist was 20, and good friends with another Jenner-Kardashian ex, Justin Bieber.
Lil Twist Today
Following his relationship with Kylie Jenner, it looks like Lil Twist got all twisted up. He got arrested in 2013 for driving Justin Bieber’s car while drunk, and then two years later he was charged for assaulting Corey in the House star Kyle Massey, as well as his brother, Chris.
Following that he was also charged with grand theft, assault, making threats, and breaking and entering. Of his year-long sentence, he only served two months.
Anwar Hadid And Kendall Jenner
Let’s end things off with another one of Kendall Jenner’s lowkey relationships. Before Kendal and Ben Simmons were in a relationship, for a short while, she was with the model Anwar Hadid.
His mother is famous for being on Real Housewives, and his father is the property mogul, Mohammed Hadid. He’s also the brother of Gigi and Bella Hadid. It’s said that Jenner was spotted kissing Hadid while she was still with Simmons. Scandalous indeed.
Anwar Hadid Today
Anyone who watched The Real Housewives of Beverly Hills regularly got to see Anwar grow up. These days he’s in a committed relationship with the pop singer Dua Lipa. The two were frequently seen together in London, during the coronavirus pandemic.
Following that, they moved back to the United States to be with the Hadid clan. This was all after the power couple went on a huge whirlwind tour of Eastern Europe and the Netherlands.