The Kardashian-Jenner family has encountered a wide range of ex-lovers. Models, music singers, athletes, and rappers all made the reality TV royal family’s list of ex-boyfriends. After dating one of the siblings, some ex-Kardashian-Jenners have claimed they experienced “The Kardashian Kurse.” Check out some of the well-known people that have dated the Kardashian-Jenners in the past.
The Kardashian family’s initial source of controversy and perhaps popularity was their ex-boyfriend Ray J. The American singer, rapper, and TV personality was charged with selling and distributing the infamous 2003 tape that depicts her and Kim K. Ray J, whose true name is William Ray Norwood Jr., is the cousin of rapper Snoop Dog and the brother of R&B artist Brandy. In 2003, Kim and Ray J were dating. Kim was 23 and the rapper was 22.
Ray J Now
After Kim and Ray J’s tape was made public a year after their breakup, the singer even followed in Kim’s footsteps and launched her own reality TV series, For the Love of Ray J, which was followed by Brandy and Ray J: A Family Business in 2010.
The singer wed Princess Love, his Love & Hip Hop: Hollywood co-star, in 2016, and the two are parents to two kids. In 2020, Love filed for divorce.
Kylie Jenner and Tyga
The large age difference between the youngest Jenner and rapper Tyga, especially in the early stages of their relationship, makes this duo problematic. They first connected in 2011 at Kendall’s 16th birthday party, the older sibling. By then, Kylie would have been 14 and Tyga would have been 21. Gulp.
The rapper started seeing Kylie after breaking off his engagement to Blac Chyna, the mother of his son, after several years. Until Kylie reached 18, the two insisted that they were “just friends.”
Although Tyga and Kylie said they would eventually get married, their relationship ended in 2017. On her ankle, Kylie previously had Tyga’s initial tattooed, with the little ‘t’ changed to read “LA.”
The rapper, whose true name is Michael Ray Stevenson, recently engaged in an online argument with the son Nick and Tana Lea of retired wrestler Hulk Hogan. Lea and Hogan both said that Tyga cheated on Kylie while they were together, and Lea also claimed that the rapper texted his girlfriend.
Rob Kardashian and Adrienne Bailon
Between 2007 and 2009, Rob was romantically linked to singer, actor, and TV personality Adrienne Bailon for two years. At the time, Bailon had achieved success with the RnB trio 3LW and the Disney girl group The Cheetah Girls. Early seasons of Keeping Up With the Kardashians featured the couple extensively; however, after Rob cheated on Adrienne, they called it quits.
The singer of “No More (Baby I’ma Do Right)” claimed that the Kardashian name had a negative impact on her career, but she has since achieved greater success.
Adrienne Bailon Now
Alongside fellow teen sensation Tamera Mowry, Bailon has co-hosted the daytime chat show The Real since 2013. Being a part of the program made Bailon the first Latina host of a daytime talk show in the US. She has also made an appearance on The Masked Singer, a reality singing competition.
Lenny Santiago, a music industry executive, and Bailon were engaged; however, they separated in 2015. In 2016, the former Cheetah Girl wed Christian musician Israel Houghton in Paris. She now has a stepmother role with his four kids.
Khloé Kardashian and Lamar Odom
Khloé, the third Kardashian sibling, wed basketball player Lamar Odom after a brief courtship. They first connected at a Lakers party in 2009, and one month later they were wed. The couple soon had their own spin-off program, Khloé and Lamar, and the wedding was a major plot point in Keeping Up With the Kardashians.
Odom, unfortunately, had addiction-related problems. Kardashian initially requested a divorce in 2013, but she later withdrew it when Odom was admitted to the hospital in 2015 so she could help him make medical decisions.
Lamar Odom Now
Odom published a memoir titled Darkness to Light: A Memoir in 2019 after receiving therapy for his health problems. The sportsman confesses to cheating on Khloé in the book and even threatens to kill her while intoxicated.
Odom was first seen with personal trainer Sabrina Parr while out and about in Atlanta. They are currently engaged. The former LA Laker recently displayed a fresh tattoo honoring Parr and called her his “wifey.”
Kylie Jenner and PartyNextDoor
Numerous relationships involving the Kardashian-Jenner family go through dry spells, at which time another athlete or rapper might slink in and grab a few dates. When Kylie Jenner and rapper PartyNextDoor were dating in 2016, when Ky was on a break from rapper Tyga, that is what transpired.
The creator of Kylie Cosmetics even appeared in PartyNextDoor’s “Come and See Me” music video. She remarked, “It never really got to the boyfriend-girlfriend stage,” when asked about her relationship with Complex. She continued by saying “It was just fun. I was doing what I wanted to do.”
The successful rapper PartyNextDoor, real name Jahron Anthony Brathwaite, has kept up his career. He has worked with Drake, Big Sean, and Jeremih. He was the first artist signed to Drake’s record company. He wrote Rihanna’s 2016 hit song “Work,” which is impressive.
The rapper was seeing R&B singer Kelani before hooking up with Kylie, but he hasn’t been romantically linked to anyone since the youngest Jenner. Fans have conjectured that PND’s 2020 song “Savage Anthem” is about Kehlani, an ex-girlfriend.
Kourtney Kardashian and Scott Disick
Where do we start, you ask? Well, well, well. In 2004, honorary Kardashian Scott Disick first got to know Kourtney, the oldest Kardashian sibling. When Keeping Up With the Kardashians premiered in 2007, Scott and Kourtney were already a couple. The program covered their ups and downs as a young socialite couple.
Mason Dash, Penelope Scotland, and Reign Aston are the three children that whom Scott and Kourtney share parental responsibility. Disick has often attended rehab, and their relationship with Kourtney was declared over in 2015.
Scott Disick Now
Despite their tumultuous marriage, Scott and Kourtney have managed to co-parent their kids and frequently hang out. In Keeping Up With the Kardashians, they may be seen taking family trips, and Scott remains close to the rest of the family.
In 2017, Disick began dating Sofia, the youngest child of Lionel Richie. The 15-year age difference between the two has drawn criticism in the media. In 2020, the couple appeared to call it quits, but they have since been sighted together.
Kim Kardashian and Nick Lachey
Nick Lachey, the frontman for the band 98 Degrees, is perhaps most known for his disastrous union and reality series with music icon Jessica Simpson. Or perhaps you are familiar with him because he hosts the Netflix dating series Love is Blind. Regardless, Nick Lachey and Kim Kardashian had a date in 2006.
In 2019, Lachey told Andy Cohen that because they had only dated once, he wouldn’t even consider Kim to be an ex. The two, hilariously, saw The Da Vinci Code together.
Nick Lachey Now
When they left the movie theater and discovered 30 photographers waiting for them, Lachey alleged that Kimmy had called the paparazzi on their date.
When Vanessa Minnillo appeared in the music video for the singer’s song “What’s Left of Me” in 2006, they became acquainted. The couple married in 2011 on Sir Richard Branson’s private island. Camden John, Brooklyn Elisabeth, and Phoenix Robert are the three children that Nick and Vanessa Lachey have together.
Khloé Kardashian and French Montana
Khloé Kardashian reconnected with Moroccan-American rapper French Montana in 2014 following the dissolution of her marriage to LA Laker Lamar Odom. Although their relationship lasted less than a year, the two have stayed friends ever since.
The “Slide” rapper talked about the relationship in a 2019 interview with E!, stating, “I feel like we had a real dope relationship, […] There was no bad blood, nobody did something to somebody that we couldn’t come back from. The love was real.”
French Montana Now
Karim Kharbouch, better known by his stage as French, and Khloé remain close pals. The rapper frequently makes cameos on the popular family reality show. At Kourtney’s 40th birthday party and after the Tristan Thompson affair, the two were seen together.
In 2019, French Montana released his third album, Montana, after becoming a citizen of the United States in 2018. The rapper has owned a variety of exotic animals, including a baby monkey named Julius Ceasor, and two tiger cubs named Ike and Tina.
Kendall Jenner and Blake Griffin
Between 2017 and 2018, model Kendall Jenner dated Blake Griffin, a player with the Los Angeles Clippers. Kendall kept the specifics of their relationship private, as she did with the majority of them. The basketball player’s long-term relationship with Brynn Cameron, the mother of his children and his fiancée, was actually ended by this combination.
Court documents stated, “Griffin cared more about the glamour of dating a Hollywood celebrity than the day-to-day responsibilities of being a father and family man.”
Blake Griffin Now
When Blake relocated to Detroit to play for the Detroit Pistons, their romance came to an end. Due to his recuperation from knee surgery, the basketball player missed the first 10 games of the 2019–2020 season. Griffin underwent surgery on his other knee after making a full recovery, and he will now likely miss the remainder of the basketball season.
Since his breakup with Kendall, the sportsman has been seen with a number of women, including pop sensation Tinashe and Fox Sports Detroit reporter Brooke Fletcher.
Khloé Kardashian and Rashad McCants
There are a lot of basketball players on this list, so be warned. After being introduced to Rashad McCants by NFL player Reggie Bush, Khloé started dating the former professional basketball player in 2008. Bush and Kim Kardashian were dating at the time, so Khloé hung out with a guy of her own.
Rashad and Khloé’s relationship lasted just seven months, but you can still see the NBA player on a Kourtney Kardashian episode.
Rashad McCants Now
Rashad McCants made the same claim about being with a Kardashian having an adverse impact on his career as many other men associated with the Kardashian family have. The athlete said that he would have been a “$60-70 million player” in an interview with the Charlotte Observer in 2017 if he hadn’t dated Khloé.
McCants failed to report to his team, the Cleveland Cavaliers, following his separation with Khloé, which was purportedly caused by his cheating. Following that, he participated in the BIG3 league while playing basketball abroad.
Kylie Jenner and Cody Simpson
In 2011, Kylie and Australian pop sensation Cody Simpson were both teenagers when they started dating. Although the relationship was obviously not very serious, it is not surprising that the reality celebrity and the blonde adolescent hero dated for a while.
Through her brief romance with Cody, the young beauty mogul met her friend and soon-to-be ex-boyfriend Jaden Smith, which resulted in some significant introductions. Jordyn Woods, Kylie’s former best friend, was then introduced to her by Smith.
Cody Simpson Now
Since his relationship with Kylie, the “Pretty Young Eyes” singer has dated a number of stunning A-listers. Between 2013 and 2015, he was romantically linked to model Gigi Hadid, a close friend of Kendall’s. He’s been seeing Miley Cyrus, an ex-Disney starlet and music sensation, more lately.
Simpson has dabbled in acting as well and has landed a major Broadway part. The singer enjoyed a successful run on the Australian version of the singing reality show called “The Masked Singer ” before landing the role of Dmitry in Anastasia.
Kylie Jenner and Jaden Smith
If you haven’t noticed it already, Will and Jada Smith named their children variations of their own names. As a result, we have Will and Jada, Willow, and Jaden Smith. That is now Hollywood. Anyway, Jenner went on to another Hollywood offspring, Jaden Smith, after her brief romance with Cody Simpson.
In 2013, Kyle dated the Karate Kid actor and got to know ex-BFF Jordyn Woods thanks to the Smiths. After their youthful romance, Jenner and Smith maintained their friendship.
Jaden Smith Now
Anyone who keeps up with the Kardashian-Jenner family is aware that the news that Tristan Thompson had cheated on Khloe with Kylie’s live-in best friend Jordyn Woods led to a major divorce. Jaden and Kylie’s friendship suffered as a result of the Smith family supporting Jordyn during the controversy.
Jaden has followed the wacky celebrity-child path, starting with his desire for emancipation at the age of 15 (it’s the equivalent of divorcing your parents). The actor, who was raised without the usual rules or education, is now a conspiracy theorist.
Kim Kardashian and Nick Cannon
Kim Kardashian dated rapper, actor, and comedian Nick Cannon before her name was plastered across every tabloid and gossip website. The reality star wore a variety of mid-’00s fashion and beauty trends while the couple was dating from 2006 to 2007.
In actuality, Kim wasn’t yet well-known at the time; she was working as Paris Hilton’s stylist. When Kim’s infamous footage with Ray J was exposed, the couple broke up because Cannon believed the young socialite had shared it herself.
Nick Cannon Now
In 2008, the Wild ‘N Out presenter tied the knot with the legendary Mariah Carey. Daughter Monroe and son Moroccan Scott are the couple’s twins; they were united in marriage in the Bahamas. Sadly, Cannon and Carey divorced in 2016. Their split occurred in 2014.
2017 saw the birth of Cannon’s second child, Golden Sagon, with model and beauty queen Brittany Bell. Cannon is a well-known television host who has also participated in the reality singing competition The Masked Singer and presented America’s Got Talent.
Kourtney Kardashian and Joe Francis
Celebrities frequently have shady relationships, and the Kardashian-Jenner clan and Joe Francis are no exception. Francis is best known for the sleazy entertainment business Girls Gone Wild, which preys on college-age girls who are out having fun.
The Kardashian siblings have frequently appeared in episodes of Keeping Up With the Kardashians, and Francis and his residences have been featured. Joe and Kourtney allegedly had a brief relationship, but more significantly, he introduced her to Scott Disick, the father of her children.
Joe Francis Now
Joe Francis has dealt with a variety of legal problems. Tax evasion, wrongful incarceration, violence, bribery, and intimidating a witness were all found to be true. And to make matters worse, he entered a no-contest plea to charges that included child abuse.
Francis served 339 days in jail in 2003, and in 2013 he was given a sentence of 70 days in county jail, 36 months probation, and an anger management course. Francis has two daughters with Abbey Wilson, who won the Girls Gone Wild “Search for the Hottest Girl in America” Francis served 339 days in jail in 2003.
Rob Kardashian and Rita Ora
The only Kardashian-Jenner son dated Rita Ora back in 2012. Less than a year into their relationship, Rob and Rita kept their union quiet in front of the media. This relationship, like the majority of Rob Kardashian Jr.’s, ended in turmoil.
Rob Jr. accused singer Ora of cheating on him with “almost 20 fellas,” calling her relationship with him “a phase” and calling her time with him “just a phase.” Kardashian tweeted a string of irate remarks about Ora, as is his habit.
Rita Ora Now
Before dabbling with the Kardashians, Rita Ora was already well-known, and she has proceeded to have success in the music industry. In 2018, the singer from Kosovo launched her second album, Phoenix, and with the help of the track “Let You Love Me,” she became the first British female solo artist to have 13 UK Top 10 singles.
Ora dated the Scottish DJ Calvin Harris from 2013 to 2014, Tommy Hilfiger’s son Ricky from 2014 to 2015, and Andrew Garfield, the star of the Amazing Spider-Man, from 2018 to 2019.
Kendall Jenner and Jordan Clarkson
Jordan Clarkson is one of many professional athletes whom the Kardashian-Jenners date. The LA Lakers and Cleveland Cavaliers, who are essentially the dating teams for the reality star sisters, are where the Filipino-American basketball player played for. From 2016 until 2017, Kendall and Jordan had a brief relationship.
Kendall and Jordan were seen together at Coachella, and while Jordan played for the LA Lakers, Kendall went to a number of his games. Given that Clarkson once dated the model Chanel Iman, he obviously has a thing for them, just like Kendall Jenner does for basketball players.
Jordan Clarkson Now
Clarkson was traded after his stint with Kendall, first to the Cavaliers in 2018 and subsequently to the Utah Jazz in 2019. Bella Hadid, a fellow model and Kendall’s close friend, was said to be dating Clarkson in 2018, but the Palestinian-Dutch model later denied these claims on Twitter.
Ally Russel, the ex-girlfriend of another NBA player Lonzo Ball, is currently dating Clarkson. In Utah, where the athlete’s team is currently situated, Clarkson and Russell shared photos of themselves.
Kim Kardashian and Kris Humphries
Kim K has been married three times; her second union was with Kris Humphries, a former collegiate and professional basketball player. Kimmy seemed to be eager to walk down the aisle even though viewers of Keeping Up With the Kardashians were aware that something wasn’t quite right between these two.
Kim and Kris began dating in 2010, and they got engaged and married in 2011—barely a full year had passed. The opulent wedding was broadcast as a two-part special on E!
Kris Humphries Now
The viewers saw Kim break down on television as she claimed that she didn’t love her new spouse as much as she should have given the fact that this famed catastrophe of marriage only lasted 72 days. The divorce took approximately ten times as long as the marriage, and by the time it was finally finished, Kim had already moved on with her husband Kanye West.
As for Kris, it is understandable that he defended himself in the face of claims that the couple was a fraud. Since leaving the NBA, Humphries has started dating Kim doppelgänger Fatmire Sinanaj.
Kendall Jenner and A$AP Rocky
The Kardashian-Jenner family isn’t just interested in hooking up with famous athletes; they also like professional musicians. In 2016, rapper A$AP Rocky and Kendall dated and went to the Met Gala together. Due to their incompatible schedules, this couple dated for more than a year before calling it quits.
Since they “weren’t really official” at the time, according to the rapper and model, calling it quits when they “weren’t seeing one other a lot” made sense.
A$AP Rocky Now
Since his breakup with Kendall, A$AP has experienced some fairly dramatic events. The rapper was previously sentenced in 2004, and following a brawl in 2012, 2013, and 2014, he was arrested. Rapper “Babushka Boi” engaged in more altercations in Canada and New Zealand in 2019 and 2016.
When the rapper was officially accused and imprisoned in Sweden following a street fight, he became the center of attention. A$AP was detained in Sweden for one month.
Kourtney Kardashian and Younes Bendjima
Kourtney Kardashian’s turbulent almost ten-year relationship with Scott Disick ended when she began dating Algerian model Younes Bendjima. The two got to know one another while Kim K was being held hostage and robbed in Paris. When the break-in occurred, both celebrities were present for Paris Fashion Week and were together.
Younes is 15 years younger than Kourt, just like Scott’s new girlfriend Sofia, who is her ex. They spent a lot of time together lounging on yachts, but they broke up in 2018.
Younes Bendjima Now
Kourtney was subjected to some fairly controlling behavior from Younes, who chastised and questioned her for sharing provocative bathing suit photos on Instagram. The two have nevertheless maintained a close relationship, and there have even been reports of a reconciliation.
A man who asserted that Bendhima, rapper Drake, and NFL player Odell Beckham Jr. attacked him at a West Hollywood nightclub in 2018 sued them in 2019. Younes dated Scott Disick’s girlfriend Sofia Richie and model Jourdan Dunn before dating Kourtney.
Rob Kardashian and Blac Chyna
This list includes Blac Chyna, who was Tyga’s girlfriend and the mother of his child before he dumped her for Kylie Jenner, who was underage. Being friends with Kim in the past and becoming best friends with Kanye West’s ex-girlfriend Amber Rose put Chyna outside the Kardashian-Jenner circle. Do you intend to continue?
Rob Jr. was the lone male Kardashian, so Chyna eventually pursued him. In 2016, the two announced their engagement.
Blac Chyna Now
Dream Renee Kardashian was born to Chyna, real name Angela Renée White, and Rob in 2016, and the couple split up in 2017. Chyna filed a lawsuit against the Kardashian family for lost revenue when their reality program Rob & Chyna, which chronicled their rocky relationship, was unable to be renewed for a second season.
Following claims, exposed pictures and videos, and a restraining order, Chyna and Rob do not get along. Sage the Gemini, a rapper, and the model are allegedly dating.
Kim Kardashian and Damon Thomas
While many people are aware that Kim K married Kris Humphries and Kanye West, not everyone is aware that she has also been married three times overall. Kimmy eloped with music producer Damon Thomas at the age of 19, and she admits that she wasn’t in the correct headspace at the time.
Three years later, in 2003, Thomas ultimately filed for divorce. Since then, Kim has admitted that Thomas abused her both physically and mentally while they were married. She had moved on with Ray J before their divorce was officially formalized.
Damon Thomas Now
In 2010, Thomas and Kardashian’s divorce documents were published, and the producer came forward to refute the abuse claims. He made the same accusations against the reality star as many other ex-partners of the Kardashian-Jenner family. Kim said that Damon persuaded her to quit college and get aesthetic surgery, but he also accused her of cheating on him and having a celebrity obsession.
Damon Thomas continues to produce music and movies and has a son with his ex-girlfriend, Sarai Torres.
Kourtney Kardashian And Justin Bieber
A strange celebrity pairing is here! The Biebs has been linked to Kendall and Kylie, but after her breakup with Scott Disick, he also started seeing Kourtney, the oldest sister.
Just before Justin Bieber made his relationship with Hailey Baldwin public in 2015, Kourtney and Justin were spotted out and about at various clubs. When questioned about his relationship with Kourtney, Justin claimed that nothing was happening and that he had known the family for a long time. Yes, Justin.
Justin Bieber Now
The Biebs is undoubtedly a megastar in his own way and has dated several stunning A-listers. Beginning in 2010 and concluding in 2018, the Canadian singer-songwriter had a protracted on-and-off romance with Selena Gomez, a pop artist. A long-term on-again, off-again romance between the “Sorry” singer and model Hailey Baldwin began in 2015.
Justin and Hailey may have already been legally married before their 2019 wedding, which took place in South Carolina.
Khloé Kardashian and James Harden
Khloé Kardashian hasn’t had a lot of luck in relationships, and hers with James Harden was no exception. At her brother-in-law Kanye West’s birthday celebration, Koko met the professional basketball player. They dated from 2015 to 2016.
Sadly for this Kardashian, Harden cheated on her. The reality star said, “He wanted [a relationship]. I wanted it, but I wanted to be realistic. He sought me out. He wanted to be committed and, you know, then wasn’t committed. So Koko had to go go!”
James Harden Now
Despite being rivals of the Kardashian-Jenner family, Harden and Jordyn Woods are reportedly just friends. The player is an eight-time NBA All-Star and one of the league’s top scorers.
The basketball player has been romantically linked to R&B singer Ashanti, model Amber Rose, Kanye West’s ex-girlfriend, models Lesanik and Brittany Renner, and reality TV actress Malaysia Pargo. He is presently thought to be dating Instagram influencer and cybersecurity consultant Gail Tiffany Golden.
Rob Kardashian and Rihanna
We bet you didn’t notice or didn’t remember this one! That’s right, the oddball Robert Kardashian Jr. once dated Ms. Robyn Fenty, a.k.a. Rihanna, the queen of everything. RiRi and Rob had a hilarious first date that included go-karting and a night out at the Playhouse nightclub in Los Angeles.
In 2012, after Rob’s breakup with Rita Ora and after Rihanna’s breakup with rapper Chris Brown, this short-lived couple spent time together. RiRi and Brown restarted their relationship after her time with Rob.
When she briefly dated Rob, Rihanna was already a pop icon, and she has since dominated every endeavor she undertakes. The Barbadian singer released the number-one album Anti in 2016 after winning a Grammy for her debut album Unapologetic in 2012.
In addition to the lingerie line Savage X Fenty, the singer also introduced the critically praised Fenty Beauty line in 2017. Between 2009 to 2016, the “Umbrella” singer had a sporadic relationship with rapper Drake. From 2017 until 2020, the singer dated Saudi businessman Hassan Jameel.
Kendall Jenner and Lewis Hamilton
Model Kendall Jenner is known for keeping her relationships under wraps. She avoids declaring her love in front of others and rarely verifies her relationship status. Therefore, we cannot know for certain how serious her hookups are, but it does not preclude us from making assumptions!
Lewis Hamilton, a British racing driver, and Kendall were seen together twice in 2015. First, while watching one of his races, she was seen sporting the chain worn by the six-time Formula One World Champion. After then, they were seen together when attending New York Fashion Week.
Lewis Hamilton Now
Hamilton has the records for the most career points, the most pole positions, and the most grand slams in a season, making him one of the most successful drivers in Formula One history.
The racer dated Nicole Scherzinger, the lead singer of the Pussycat Dolls, from 2007 to 2010 and then from 2011 to 2015, on and off. Then, in 2015, Rita Ora, Winnie Harlow, and Rihanna were all photographed with him. Since then, other models have been connected to the driver.
Kourtney Kardashian and Luka Sabbat
Another speculated but unconfirmed Kardashian romance involves Grown-ish actor Luka Sabbat and Poosh creator Kourtney. Kourtney has no issues dating younger men, and the age difference between these two is fairly wide—nearly 20 years. The actress had previously modeled for Yeezy Season 1 in 2015, and Kourt and Luka were seen together in 2018.
Sabbat attended Kanye West’s Sunday Service at Coachella in 2019 and is close with the entire Kardashian clan.
Luka Sabbat Now
Since his alleged hook-up with Kourtney, Sabbat hasn’t appeared to be dating anyone, as far as we know. The actor frequently appears in group photos with Kendall, the younger sister of Kourt, and other model friends. Sabbat identifies as a “creative entrepreneur […], stylist, creative director, design director, actor, model, etc.” on his website.
The “It” boy of Gen Z, who has more than 2 million Instagram followers, has acted as an influencer for brands like Calvin Klein and Evian.
Kylie Jenner and Travis Scott
Rapper Travis Scott and beauty entrepreneur Kylie Jenner first crossed paths at Coachella in 2017. The reality personality made the decision to pack up and follow the rapper on his tour. After concealing her pregnancy for just one month, Kylie became pregnant and gave birth to their daughter Stormi Webster in 2018.
2019 saw the breakup of Travis and Kylie amid allegations that the rapper had cheated. They assert that they are “on good terms” and that they are co-parenting their daughter.
Travis Scott Now
Some people even believe that Kylie and Travis faked their break-up because there are speculations that they are still together. People may have thought the two were married at one point, but Kylie insists that she and Travis are better as friends than as a couple.
Scott, real name Jacques Berman Webster II, has been following musician Iggy Azalea on Instagram and has expressed admiration for her. Fans questioned whether there was a relationship between Azalea and the “Antidote” rapper after the rapper liked several of the singer’s photos.
Kendall Jenner and Chris Brown
Chris Brown has already appeared on this list, but he regrettably does so once more as a result of an alleged relationship with Kendall Jenner. The majority of people are familiar with Chris Brown as Rihanna’s violent ex-boyfriend who has persisted in the music business. Pictures of the Barbadian singer’s bruises stunned the entire globe in 2009.
Brown is reportedly close to Tyga, Kylie’s ex-boyfriend, and a member of the Kardashian-Jenner family. There are rumors that Kendall and Brown slept together in 2014 and then again in 2016.
Chris Brown Now
Chris Brown appears to keep returning despite being accused of felony assault for allegedly assaulting and threatening Rihanna. Brown has been a part of numerous violent episodes, such as a fight with Drake and his crew and an altercation with the artist Frank Ocean.
In 2013, the singer was involved in a hit-and-run, and in 2016, she was charged with making a gun threat to a lady. After this encounter, Brown and the LAPD and a SWAT squad engaged in a standoff at his home.
Kim Kardashian and Gabriel Aubry
Before meeting controversial rapper Kanye West, Kim Kardashian tried some of Hollywood’s most eligible men. When he was sighted out and about with Kim K, Canadian model Gabriel Aubry had recently ended a five-year romance with actress Halle Berry.
The attractive couple was spotted spending Thanksgiving together, watching Burlesque in theaters, and going to a Laker’s game together. Before Kim moved on with her second husband Kris Humphries, this couple split up.
Gabriel Aubry Now
Halle Berry and Aubry had a contentious custody dispute after their breakup in 2010. So Berry could live with her new fiancé, actor Olivier Martinez, she essentially wanted to relocate their daughter Nahla Ariela Aubry to France.
There was conflict between Berry’s former and current partners, which resulted in a fight. Martinez ultimately obtained a restraining order against Aubry, barring him from approaching Berry or their daughter within 100 yards. Thankfully, they were able to work something out in court.
Kourtney Kardashian and Taryll Jackson
Since several of the Jackson and Kardashian-Jenner siblings have dated in the past, it’s not surprising given their long-standing friendship. Taryll, the son of Tito Jackson, and Kourtney dated for four years in the early 2000s. The families remain close.
In 2018, The Jacksons and Kardashian-Jenners competed against one another in a softball game for charity. The “Calabasas Peaches” and “Tito’s Team” squared off in the match, which was featured in a Kardashians episode.
Taryll Jackson Now
Together with his brothers Toriano and T.J., Taryll Jackson makes up the pop group 3T. He has also been a successful songwriter for Lindsay Lohan, Bruno Mars, and his aunt Janet Jackson. Jackson has kept up his solo career and joint performances with his family.
In 2012, Taryll released his first solo album. Later that year, he made an appearance on The Jacksons: Next Generation alongside his brothers Taj and T.J. Since their relationship began in 2006, Taryll and Breana Cabal have been parents to two kids.
Kendall Jenner And Ben Simmons
Another ex of the Kardashian-Jenner family who may not exactly be an ex is this one. We can never be really sure! Like her sisters, Kendall enjoys dating basketball professionals, so when she began dating NBA player Ben Simmons in 2018, we weren’t shocked.
Jenner and Simmons were first spotted dining out together in Beverly Hills before going out to party at Vandal in Manhattan. Thankfully, Kendall acknowledged their relationship in 2019 when TV personality Ellen DeGeneres inquired about it.
Ben Simmons Now
Kendall has since been spotted with other men, so it’s unclear if she and Ben are still together. While Jenner lives in both California and New York, the professional player spends his time in Philadelphia with his team, the Philadelphia 76ers.
The basketball player from Australia and America hasn’t been linked to anyone since Kendall, but he has a few well-known ex-wives. He dated singer Tinashe in 2018 after dating former women’s basketball star Dylan Gonzalez in 2017.
Khloé Kardashian and Tristan Thompson
Can you believe the Tristan Thompson drama hasn’t been discussed yet? Our relationship may be the most disastrous on this list—aside from Kim’s 72-day wedding—! The happy ending Koko ultimately experienced with NBA player Tristan Thompson delighted fans.
Sadly, Thompson cheated on Khloé again when she, mercifully, took him back, this time while she was nine months pregnant. The second time, Thompson went out with Jordyn Woods, the best friend of Khloé’s younger sister. Unforgivable.
Tristan Thompson Now
Amazingly, Khloé still makes room in her life for Tristan because she wants to be able to co-parent with him their baby True Thompson. The pair split up in the wake of the Jordyn controversy in 2019 after a barrage of media coverage.
We won’t hold our breath, since Thompson apparently lives in Calabasas, just a half-hour drive from Khloé. Did we mention that when he first started dating Khloé, he abandoned another pregnant woman? Boo! Sadly, there are still allegations that Khloé and Tristan are dating in secret.
Rob Kardashian and Demi Lovato
Rob Kardashian dated a lot of attractive women in his earlier years. Rob was a man about town, whether he was partying with Rita Ora or going go-karting with Rihanna. Robert Jr. and Demi Lovato, a former child star and singer-actress, were seen bowling together in 2010. Is it true that this man adores an adventurous date?
Rob sweetly invited Kylie and Kendall, his younger sisters, to see Demi perform in Los Angeles. This relationship was presumably low-key and brief. No drama at all!
Demi Lovato Now
Throughout her career, the former Barney & Friends star battled addiction and had to stay in rehab. Lovato has dated a good number of eligible bachelors in the past.
In addition to dating mixed martial artists Luke Rockhold and Guilherme “Bomba” Vasconcelos in 2016 and 2017, the “Sorry, Not Sorry” singer was romantically linked to actor Wilmer Valderrama from That ’70s Show between 2010 and 2016. Additionally, Lovato has dated models Austin Wilson and Henri Alexander Levy. Actor Max Ehrich and she are dating at the moment.
Kim Kardashian and T.J. Jackson
It should come as no surprise that Kim dated Taryll Jackson given that Kourtney Kardashian dated him for a number of years. for some time. Kim and T.J. are real. were each other’s first loves and high school sweethearts. The 3T singer admitted to dating Kim from the time he was 14 until he was 18 years old to The Boombox. Aww! He said that it was “puppy love.”
Images of T.J. and Kim are a little hazy, but it’s clear that they’re excited to go to prom together.
T.J. Jackson Now
T.J. is a member of the musical group 3T alongside his siblings and has made appearances on several reality TV programs. In 2007, he wed his longtime companion Frances Casey, and the two became parents to four kids.
Son Royal, daughter Dee Dee, daughter Jo Jo, and son Rio were all born between 1999 and 2015. Sage and Lexci are the names of Jackson’s two stepchildren from Casey’s previous union. T.J. has sole custody of Paris, Prince, and Blanket Jackson, Michael Jackson’s children.
Kendall Jenner and Orlando Bloom
Another one of Kendall Jenner’s sexy hidden men is shown here. The Lord of the Rings actor Orlando Bloom was said to be dating the model back in 2015. As usual, Jenner declined to confirm the relationship, and Bloom even claimed to not have the model’s phone number.
The Pirates of the Caribbean actor was spotted out and about with Kenny after divorcing Miranda Kerr in 2013. It’s probably for the best that this celebrity couple’s relationship didn’t last given their close to the 20-year age difference.
Orlando Bloom Now
Happily, Bloom is now married to a person who is closer to his own age, and the couple is even expecting a new baby. The British actor currently has a daughter on the way with pop sensation Katy Perry after previously having a boy with his ex-wife, supermodel Miranda Kerr.
Bloom began seeing the “Hot N Cold” singer in 2016, and on Valentine’s Day of 2019, the actor proposed. Although there were a few hiccups along the way (no pun intended), these two appear to be on the right track.
Kim Kardashian and Reggie Bush
Since they dated from 2007 to 2009, Reggie Bush was Kim’s first boyfriend to ever feature on Keeping Up With the Kardashians. Bush is a former professional athlete, this time a running back in American football, which is not surprising. At the 2007 Espy Awards, former quarterback Matt Leinart introduced these two to one another.
Bush and Kardashian were a very beautiful couple when they were dating; they were both in their twenties at the time. Due to Kim’s rising prominence, the football player and reality star decided to part ways.
Reggie Bush Now
In 2010, Bush was linked to country singer Jessie James after dating Kim. Bush married Armenian dancer Lilit Avagyan in 2001, so he obviously has a thing for Armenian women.
Bush and Avagyan are parents to three children: son Agyemang (born in 2017), daughter Briseis (born in 2013), and sons Uriah (born in 2015). Along with having a similar cultural background, Bush’s ex and his wife also have striking physical similarities. Many people online have compared Avagyan to Kim K.
Kim Kardashian and Miles Austin
Kim made the decision to date another professional player after breaking up with Reggie. Kiki chose a wide receiver who played for the Dallas Cowboys this time. Compared to her time with Reggie, Kim’s relationship with Miles was less public, but she insisted that it was still serious.
Due to their demanding schedules, these two ultimately broke up. Kim was traveling to Europe to film Keeping Up With the Kardashians while Austin was preoccupied with the football season. That is life.
Miles Austin Now
Austin started working as a football coach and scouting intern after he retired. He has served as head coach of both the San Francisco 49ers and the Dallas Cowboys.
In 2014, Miles wed Cowboys cheerleader Stacy Sydlo. Maven, Ava, and Miles IV are the names of the couple’s three children. In 2019, Austin made the decision to return to school to finish his degree. The former athlete graduated with a history degree and claimed he did it to demonstrate to his children that you can “finish what you start.”
Kendall Jenner and Harry Styles
Harry Styles, a former member of One Direction, and Kendall were first spotted together in 2013 and have since been spotted together frequently. Fans were unsure of just how close these two were because Kendall, as always, was coy about the relationship.
When the singer and model participated in “Spill Your Guts Or Fill Your Guts” on The Late Late Show in 2019, they later disclosed more information about their relationship. The two oozed chemistry and engaged in plenty of flirting.
Harry Styles Now
Since his time with Kendall, the former X Factor contestant has had a very successful career and is still moving up the ranks. In 2019, the musician released his second album, Fine Line, and made his acting debut in Christopher Nolan’s Dunkirk.
Since One Direction disbanded, the English singer has been embracing his gender fluidity and dressing in an eccentric manner. Styles dated Victoria’s Secret Angel Camille Rowe from 2017 to 2018, and the two are reportedly back together.
Kylie Jenner and Lil Twist
We are aware that every Kardashian-Jenner changes partners frequently and will move on to another athlete or rapper if they are dissatisfied with their present partner. In 2013, Kylie and the rapper Lil Twist experienced this. Kylie had a brief romance with the “Little Secret” rapper after her connection with Jaden Smith and before her committed union with Tyga.
Kylie was only 15 years old when she was seen with Justin Bieber’s close friend Lil Twist, who is now 20.
Lil Twist Now
Following his alleged romance with Kylie, Lil Twist’s situation didn’t turn out so well. He was detained in Calabasas in 2013 for drunken driving while operating Justin Bieber’s vehicle. After assaulting actor and comedian Christopher Massey and his brother, rapper and singer Kyle Massey, he had yet another run-in with the law in 2015.
The rapper was taken into custody on suspicion of breaking and entering, grand theft, violence, assault with a deadly weapon, and making threats. His one-year prison term was fulfilled by him over seven and a half weeks.
Kendall Jenner and Anwar Hadid
Did you believe Kendall Jenner’s sporadic and covert hookups were over? Well, we still have one! Apparently, Kendall was seen kissing model Anwar Hadid before she started dating Australian professional basketballer, Ben Simmons.
Anwar, the youngest child of real estate entrepreneur Mohammed Hadid and Real Housewife Yolanda, hangs out with models like Gigi and Bella. Evidently, Kendall has had multiple encounters with Anwar when they were seen having sex, including when she was dating Simmons. Interesting!
Anwar Hadid Now
The Real Housewives of Beverly Hills viewers have seen Anwar Hadid develop from a shy youngster into an It Boy in front of our very eyes. Hadid and English singer Dua Lipa are currently a happy pair.