Little Black Book: 20 Guys We Totally Forgot The Kardashian/Jenner Sisters Dated

The Kardashians and the Jenners have done a lot through their life. Between modeling, their makeup and clothing lines, and their guest appearances on movies and music videos, these girls have gone from the bottom to the top and really are amazing.

For those who don’t know who the family is and how they got started, one could say that it all began in 1991 when Kim Kardashian’s mother Kris divorced her husband Robert Kardashian, who is the father of Kim, Khloe, Kourtney and Robert. That same year, Kris would go on to marry 1976 Summer Olympics decathlon winner, Bruce Jenner, who she would later have two more kids with, Kendall and Kylie.

In 1994, Robert Kardashian started to make headlines after he took on O.J. Simpson as client when he was put on trial. One could almost say that the family got their start of fame because of that trial.

Kim started to get notice in her early 20s thanks to her friendship with the one and only, Paris Hilton, but it was in 2004 that she really started to get notice when a tape with her boyfriend at the time was leaked all over the Internet.

Soon after the entire family got their own reality television show called Keeping Up with The Kardashians.

Throughout the years, the Kardashian/Jenners have had quite a few relationships, some even leading to marriage and kids. There have been some rumored flings, some quick flings, some year-long romances, and then their marriages.

Keep scrolling to read about the relationships that the world forgot ever happened.

Kim's Leading Men

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25 T.J. Jackson & Kim


T.J. Jackson, also known as Tito Joe Jackson, was Kim Kardashian’s high school sweetheart.

For those who don’t know who T.J. is, T.J. Jackson is the brother of the late singer Michael Jackson and was also a member of the hit R& B band 3T. After the death of his brother Michael, T.J. went on to claim guardianship, along with his grandmother, of Michael’s three kids, Michael Joseph "Prince" Jackson Jr., Paris Katherine Jackson and Prince Michael "Blanket" Jackson ll.

According to earnthenecklace.com, T.J. and Kim grew up as childhood friends. In 1994 they took their relationship to the next level though and started dating. Their relationship lasted for four years and it was said that T.J. was even Kim’s first partner.

24 Joey Lawrence & Kim


In 1999, Kim Kardashian was linked to Joey Lawrence, who real name is Joseph Larence Migogna Jr.

According to en.wikipedia.org, Joey Lawrence is an America Actor, musician and game show host who is best known for his roles as Joey Donavan on Gimme a Break, Joey Russo in Blossom, Joe Roman in Brotherly Love and Joe Longo in Melissa and Joey.

He also had a top single that some may say was over played in 1993. The song was called “Nothing My Love Cant Fix,” and hit #6 on the Billboard Hot 100 Airplay Chart.

The couple were not together long and just had a brief relationship.

23 Damon Thomas & Kim


Not much is known about Kim Kardashians marriage to music producer Damon Thomas, she doesn’t like to talk about it much.

According to zimbio.com though, the two got married in 2000 when Kim was just 20 years old. The marriage only lasted four years though and the two wound up going through a messy divorce in 2004. According to claims made by Kim, Damon was not a very good husband.

22 Ray-J & Kim


After Kim’s divorce in 2004 from music producer Damon Thomas, Kim met Ray-J. At the time of their meeting, Kim was working as a stylist and was actually a client of Ray-J’s sister Brandy.

According to zimbio.com, the relationship lasted three years. Unfortunately for Kim, though, she will never be able to put this relationship in the past seeing as the tape that got leaked on the internet was with Ray-J. It happed in February 2007 and there was a lot of back-and-forth between Kim and Vivid entertainment. In the end, they settled, and Kim got a $5 million settlement.

To this day, the tape is one of the companies highest rated X video.

21 Nick Lachey & Kim


This relationship was never confirmed, but these two were seen many times holding hands and getting pretty close for a while there, that we defiantly could tell that there was something going on behind closed doors between the two of them.

According to zimbio.com, Kim Kardashian and 98 Degrees singer Nick Lachey were seen quite a few times in 2006 getting hot and heavy. Nick Lachey was fresh off the marriage boat, having just divorced Jessica Simpson, and Kim was also freshly single after just breaking things off with Mr. J.

Khloe's Leading Men 

20 Rashad McCants & Khloe


Back in 2009, Khloe started dating NBA player Rashad McCants.

According to usmagazine.com, it was during an episode in November 2009 of Kourtney and Khloe Take Miami that Khloe brought up claims that Rashad had cheated on her with another woman.

It wasn’t until after their break up and the season of the show ended that Rashad opened up to the New York post about how the whole thing was scripted and made up. He had never cheated on Khloe.

19 Derrick Ward & Khloe


After her break up with Rashad McCants in 2009, Khloe didn’t waste any time and quickly hooked up with football player Derrick Ward.

According to usmagazine.com, the two lovebirds were seen getting pretty cozy with one another down in Mexico. The whole family had taken a family trip in honor of Khloe’s sister Kourtney’s 30th birthday.

At the time of their relationship, Derrick was a running back for the Tampa Bay Buccaneers. Before that he has been linked to the New York Jets and the New York Giants, whom he won the 2008 Super Bowl with vs the Patriots.

18 Matt Kemp & Khloe


That same year Khloe was linked to Derrick Ward and Rashad McCants, Khloe also met her first husband, Lamar Oden. The pair were married after only one month of dating and were together for three years before she filed for divorce.

According to usmagazine.com, shortly after the divorce Khloe started seeing baseball star Matt Kemp. It was during a concert with Drake, John Legend and Jay Z in December 2013 that the couple were first seen together.

It is said they didn’t date long due to Khloe lawyers telling her to put the brakes on their relationship, so she didn’t look so bad during her divorce with Lamar.

17 French Montana & Khloe


During the year 2013 and 2014, Khloe Kardashian was linked to rapper French Montana. The two dated off and on through the two years until they finally decided to end it for good in December 2014.

According to usmagazine.com, Khloe reported that she wasn’t ready to date just yet. She was still broken up about her failed marriage to basketball star Lamar Oden.

“I jumped into something because I was just, like, lonely and destructive,” she said during an episode of Kourtney & Khloe Take the Hamptons. “But now I’m like, I just want to be alone."

16 Rick Fox & Khloe


It wasn’t long after her break up with rapper French Montana that Khloe was seen out and about with retired NBA player Rick Fox.

According to usmagazine.com, the pair started their relationship in May 2015. They were first seen on a romantic date at the Mexican hot spot called Casa Vega in L.A.’s Sherman Oaks neighborhood.

One person who was able to observe the couple on their date as they sat at the bar had this to say during an interview with Us:

“It looked to be a fun date. She seemed happy.”

Kourtney's Leading Men 

15 Younes Bendjima & Kourtney


According to reports, Kourtney Kardashian first started dating Younes Bendjima back in 2016. It wasn’t until May 2017 though that the couple became public with their relationship.

According to earnthenecklace.com, the duo first met at Paris Fashion Week in October 2016 and hit it off right away. They were then seen doing some pretty hot and heavy PDA on several occasions while on vacation together.

The couple have yet to confirm it yet, but it is pretty obvious they are no longer together, especially since Bendjima was seen partying it up in Mexico with Jordan Ozuna recently.

14 Justin Bieber & Kourtney


Justin Bieber was only 21-years-old when rumors started that he was dating Kourtney Kardashian.

According to earnthenecklace.com, the two were spotted on several occasions hanging out together, but to everyone around them, they looked pretty intimate.

Kourtney has been given the cougar tag before in the past and fans were certain that these two were an item, but the rumors didn’t last long and the two went their separate ways.

During an interview with Us Weekly, a source close to Kourtney claimed she regretted ever messing with Justin. “She feels like she’s being punished, and it goes to prove her initial instinct that Justin is too young and too immature for her. She is kind of beating herself up for ever getting involved with him in the first place,” the source told Us Weekly.

13 Michael Girgenti & Kourtney

via instagram

For anyone who does not know who Michael Girgenti is, well he is the actor who claims that Kourtney and Scott Disick’s son Mason is actually his and not Scott’s son.

According to earnthenecklance.com, it all started back in 2013 when Michael released a photo of himself as a kid and put it next to Mason’s baby photo. He claims that Kourtney and himself hooked up back in 2008 after they met at a photoshoot.

Michael was so adamant that the child was his that he even took Kourtney to court to try and get custody of Mason.

To this date there has been no proof who the father really is. No DNA test was ever taken since the Kardashian clan thought it was all a load of crock.

12 Joe Francis & Kourtney


Those who don’t know who Joe Francis is, well he is the creator of the Girls Gone Wild brand and also a family friend of the Kardashian family.

According to earnthenecklace.com, the couple supposedly dated for seven months back in 2005. It is uncertain though if the couple really were a couple, or if it was just a fling. Supposedly it is Joe who played Cupid and hooked Scott Disick up with Kourtney.

“I introduced Kourtney and Scott at my house in Mexico. Scott came as the guest of a friend of mine, and they met in my master bedroom,” he told In Touch Weekly.

11 Taryll Jackson & Kourtney


Earlier it was reported that Kim Kardashian’s first love was T.J. Jackson, whom she dated in 1998. Well, Kim wasn’t the only one to date one of the Jacksons 5.

According to earnthenecklace.com, Kourtney Kardashian became quite smitten with T.J.’s older brother Taryll Jackson. In 2001 the two started a budding relationship and dated for four years.

The Kardashian kids grew up pretty close to the Jackson kids. It is no wonder that they dated as teenagers. To this day they are still pretty close. Kourtney has even babysat for T.J.’s son Royal.

Kendall's Leading Men 

10 Anwar Hadid & Kendall


For those who don’t know who Anwar Hadid is, he is the little brother of models Gigi and Bella Hadid.

According to ranker.com, there were rumors back in June 2018 that Kendall was dating Anwar Hadid after the pair were seen kissing at a New York City after-party.

What makes this such an interesting story is that at the time they were seen, Kendall was supposedly still dating Ben Simmons.

The two officially broke up in September 2018 and since then Kendall has been seen out with Anwar a few times during Fashion Week in Paris.

9 Blake Griffin & Kendall

via detroitnews.com

It was in August 2017 that Kendall first started dating Blake Griffin, who at the time was playing for the team the Los Angeles Clippers.

According to ranker.com, for those who don’t know who Blake is, he is a professional basketball player who is currently playing for the Detroit Pistons of the National Basketball Association. Since signing with the Los Angeles Clippers in 2009, he has gone on to be a five-time NBA All-Star and a four-time All-NBA selection.

Kendall and Blake dated for almost a year before calling it quits in May 2018.

8 Ben Simmons & Kendall


Kendall moved on fast after her break up with Blake Griffin.

According to ranker.com, Kendall soon started dating NBA star Ben Simmons shortly after her break up with Blake. The rumor is that the duo was first seen together in May 2018 and were later spotted on a romantic double vacation in August 2018 with her sister Khloe Kardashian and her baby daddy Tristan Thompson.

The lovebirds were not together long though and it was reported they broke up in September 2018 after just four months of dating.

7 Harry Styles & Kendall


So, Harry Styles and Kendall Jenner never actually confirmed that they had been in a relationship together.

But, according to ranker.com, the duo was seen many times together between the years 2013 and 2016 doing romantic things like lavish yacht trips and romantic nightly dinners.

For those who don’t know, Harry Styles is an English singer, songwriter and actor. He first got his stardom when he joined the band One Direction back in 2010. It was in 2017 that he would go on to release his first solo single, “Sign of the Times,” which hit number 1 in the UK and number 4 in the US.

6 Julian Brooks & Kendall


So, there isn’t much known about Kendall’s high school sweetheart Julian Brooks.

According to ranker.com, what is known is that the couple dated from 2012 to 2013 while attending Sierra Canyon High School together.

Julian Brooks is actually the cousin of Ken Norton Jr, who has been the NFL linebacker for 13 seasons for the Seattle Seahawks, he now couches the team.

Julian himself is also a football player. He plays defensive back for the Nevada Wolf Pack.

That is all that is known.

Kylie's Leading Men 

5 Cody Simpson & Kylie


Back in 2011, Cody Simpson and Kylie Jenner were linked together romantically.

According to popsugar.com, it is not certain as to how long they dated, but it was during an appearance with E! Hello Ross, that Cody went on to talk about his short relationship with the Queen of cosmetics.

“No, the whole K-O-D-Y thing didn’t really work for me,” he said during his interview.

For those who might know who Cody Simpson is, he is a singer, songwriter, dancer, and actor. In 2017 he formed the band, Cody Simpson & The Tide, which they went on to release their first song, “Waiting For The Tide,” shortly after.

4 Jaden Smith & Kylie


For those who don’t know who Jaden Smith is, he is the son of famous actor Will Smith and actress Jaden Picket Smith. He stared along in a few movies with his father including, Pursuit of Happyness and After Earth. He has also done movies such as The Day The Earth Stood Still and the remake of Karate Kid.

According to popsurgar.com, Kylie and Jaden first started dating back in March 2013. They’re relationship did not last long though, and the duo called it quits later that same year.

It was during an issue of Seventeen’s prom issue that Kylie would confirm the couples split.

3 Miles Richie & Kylie


Miles Richie and Kylie never actually confirmed if they ever seriously dated.

But, according to popsugar.com, the two were linked together during the summer of 2014. They were seen a few times getting cozy together in the car as they drove around the big streets of La, and Miles even went on to get her initials tattooed on his hand.

For those who don’t know, Miles Richie is a singer, songwriter, musician and actor and also the only son of music legend Lionel Richie.

2 A$AP Rocky & Kylie


According to ranker.com, A$AP Rocky and Kylier Jenner were rumored to have dated for some time in 2015. It was never confirmed though.

For those who don’t know, A$AP Rocky, born Rakim Mayers, is an American rapper, songwriter, record producer and actor. One might know him from the band A$AP mob, from which he adopted his name from.

It was in 2011 that he first got noticed when he released his first mixtape, “Live, Love, A$AP. It went on to be such a success that he was handed a record deal with Polo Grounds Music, RCA Records, and Sony Music Entertainment.



For those who don’t know who PARTYNEXTDOOR is, his real name is actually Jahron Anthony Brathwaite and he is a Canadian singer, songwriter, and record producer from Mississauga, Ontario. He was the first artist to be signs to Drake’s label, OVO Sound in 2013.

According to ranker.com, it was rumored in 2016 that Kyle and he were now an item after seen out a few times getting hot and heavy. The two supposedly met while filming for PARTYNEXTDOOR’s music video, “Come and See Me,” in which they had a make out scene for.

According to an interview though Kylie did, they were never actually together officially, but just having some fun together.

Sources: earnthenecklace.com, zimbio.com, en.wikipedia.org, usmagazine.com, popsugar.com, ranker.com

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