For sixteen seasons, we’ve been Keeping Up With the Kardashians.
They are the family that has dominated headlines, tabloids, and conversations for over a decade, and we absolutely love it.
As reality television’s royal family, the Kardashians and Jenners have incidentally shared the most precious moments of their lives, from tragedies, pregnancies, and heartbreaks to transitions, celebrations, and love.
When Kim was unwittingly propelled into global infamy following her notorious sex tape, the dating profiles of every family member were also launched into the spotlight. Every fling, kiss, and date has for better or worse been documented
From Khloe’s cursed love life and Kourtney’s on-and-off relationship with the father of her children to Kim’s extravagant weddings, we’ve watched, celebrated, and cried at all the ups and downs.
Now, all eyes are now focused on Kylie and Kendall Jenner and they’re just as entertaining as their older sisters.
With a slew of rappers, NBA players, and superstars already under their belt, Kendall and Kylie continue to share their lives— albeit with a little more restraint. You’ve got
If you’re a Kardashian-Jenner fan, you know that their dating lives are basically pop culture history.
So we compiled every guy that they’ve dated and dug into why things did or didn’t last.
From NFL hunks to the rapper that won her heart, the reality star had quite the ride finding the right relationship. Despite it all, Kim has never given up on love and it only took three trips down the aisle.
Damon Thomas (2000 – 2004)
Did you know that Kim Kardashian was first married in 2000? Long before finding fame on reality TV, Kim eloped with Damon Thomas, a Grammy-nominated music producer.
Kim was just 19 years old at the time, while Thomas was 10 years older than her.
The marriage came to an end in 2004 after Kim cited controlling behavior on Thomas’ behalf, stating in her divorce papers that “Damon decided what we would do and when we would do it.”
Even more startling were allegations that he forced her to get plastic surgery.
He was definitely the wrong guy for Kim.
Ray J (2005 – 2007)
But it was the infamous sex tape the two filmed that arguably immortalized their relationship and propelled Kim into the cultural collective consciousness.
As far as gross behavior goes, Ray J can win an award for his after releasing a song titled, “I Hit It First” as a pointed diss towards Kim’s now-husband, Kanye West. Classy.
Nick Lachey (2006)
Following the fall out of dating Ray J, Kim dated 98 Degrees singer Nick Lachey right off the back of his very public split with Jessica Simpson.
While their tryst was brief, Nick came out later in an interview stating Kim had used him for fame.
“Let’s just say this,” he told Details Magazine, “We went to a movie. No one followed us there. Somehow, mysteriously, when we left, there were 30 photographers waiting outside.”
He was then asked if those paparazzi shots were the stimulus to Kim’s sudden rise to fame he answered, “That’s one way to interpret it.”
Nick Cannon (2006 – 2007)
Before Nick Cannon and Mariah Carey got married, he dated Kim Kardashian. From late 2006, the two cozied up together until the beginning of 2007 when everything fell apart because of that sex tape.
In 2012, during an appearance on The Howard Stern Show, he revealed that ‘We talked about this tape…And she told me there was no tape.”
He also added, “If she might have been honest with me I might have tried to hold her down…She’s actually one of the nicest people you’ll ever meet. But the fact that she lied and told me that there was no tape?” That was a dealbreaker.
Reggie Bush (2007 – 2010)
NFL star, Reggie Bush had a hold on Kim’s heart for a couple of years. The on-and-off couple seemed like they’d even make it work as Reggie made short cameos on Keeping Up With The Kardashians.
Even reuniting briefly following Kim’s separation from her second husband, Kris Humphries.
But, the two just couldn’t find a way to make it work, but Reggie has nothing but sweet things to say about the mogul.
In a recent interview he admitted, “she’s doing a great job creating a brand for herself, her and her family. I’m happy for ‘em … She’s very smart.”
Miles Austin (2010)
Finding a rhythm with another NFL player, Kim snuggled up with Dallas Cowboys star, Miles Austin for a few months in 2010.
Sources revealed that the relationship was strong and even the “real deal” but the distance eventually tore them apart.
“They tried to keep it as low profile as possible when they were together,” a source told People. “It was the real deal. They were always strong, but before Kim left for Europe they decided it’s not fair that they don’t get to spend more time together and ended it.”
Gabriel Aubry (2010)
When Gabriel Aubry and Halle Berry’s relationship came to an end, everyone was shocked to see Aubry move on with Kim.
Spotted out on the town and even at an LA Lakers game, Kim and Aubry had tabloids swooning over their very short fling.
According to E! factors including Halle Berry’s vocal disapproval of the new relationship, in addition to the Keeping Up star’s burgeoning crush on NBA star, Kris Humphries drove them apart.
Kris Humphries (2010 – 2011)
In December 2010, Kim and Kris Humphries began dating and things moved fast. Engaged in just six months, the relationship was heavily covered on Keeping Up With The Kardashians, as was their marriage ceremony.
The choreographed proposal, $2 million diamond ring, and $10 million wedding weren’t enough to keep them together.
The couple infamously filed for divorce just 72 days after tying the knot.
Kanye West (2012 – present)
After meeting her as Brandy’s assistant, Kanye West became obsessed with Kim.
The two began dating following years of knowing each other in 2012, and everything came together after that.
Quickly becoming pregnant with baby North West, the two tied the knot in a luxurious wedding in Italy.
“I just think that Kim is awesome,” he told Ellen Degeneres in an interview, and the sentiment hasn’t changed after 5 years of marriage.
Since Kourt spent most of her dating life in a nine-year long relationship, it’s only been in the last few years she has had to navigate her share of romantic ups and downs. Remember when it was rumored she was dating Justin Bieber? Ya, us too.
The eldest Kardashian has been in a steady relationship for most of her television career, but a hot fling suggests this hot mom is ready for some fun.
Scott Disick (2006 – 2015)
Kourt and Scott Disick were already dating when the first episode of Keeping Up With The Kardashians aired, but after 9 years the two called it quits.
The couple who very publicly aired their dirty laundry, from Scott’s infidelity, substance abuse issues, and partying habits, looked like they were going to make it despite it all, but split in 2015.
Scott is still an integral part of the family – and the show – with the two finding a way to expertly co-parent.
Younes Bendjima (2016 – 2018)
Following her breakup with Scott, Kourtney quickly began dating 26-year-old boxer and model, Younes Bendjima.
The French hunk was spotted on various yachts with the oldest Kardashian sister and the two seemed to be having a lot of fun, until Younes let all his jealousy get in the way.
After commenting on a bikini shot of Kourtney with “thats what you need to show to get likes?” the two were promptly over.
We think she’s better off!
From the end of her marriage to Lamar Odom to Tristan Thompson’s cheating scandal, it seems as if the Keeping Up With The Kardashians star can’t catch a break in her complicated love life. Luckily, she’s been blessed with a beautiful daughter and an incredibly supportive family.
The youngest Kardashian sister has had a hard time finding long-lasting and reciprocal love.
Rashad McCants (2008 – 2009)
In 2008, Khloe dated former basketballer, Rashad McCants but things didn’t go smoothly. Promptly after being photographed together on a red carpet in Las Vegas, the two experienced a tumultuous on-screen falling out.
In an episode of Khloe and Kourtney Take Miami it was insinuated that McCants had cheated on Khloe.
McCants later revealed in an interview in 2017 that he regretted the relationship because it cost him a lasting career.
“Without that situation in play I’m a $60-70 million player,” he told the Charlotte Observer. “Easily.”
Lamar Odom (2009 – 2013)
Perhaps Khloe’s most substantial relationship yet, her marriage to basketballer Lamar Odom ended in a bout of tragedy.
The two got married just one month after dating.
Exploring the ups and downs of their relationship on Keeping Up With The Kardashians their relationship ended after the former Lakers’ star struggled with infidelity and drug abuse.
Splitting up in 2013, their divorce was put on hold after Odom overdosed in a brothel in Nevada but the split was finalized in 2016.
French Montana (2013 – 2014)
While still in the midst of getting divorced from Lamar, Khloe began dating rapper, French Montana. According to Perez Hilton, the two started cozying up despite Montana being romantically to Miami rapper Trina, who was also Khloe’s friend at the time.
They only dated for a year before Khloe decided she needed to be single.
“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.”
James Harden (2015 – 2016)
Following her conscious uncoupling from French Montana in December 2014, Khloe had a few flings until she began dating another basketball player, James Harden.
The two met at Kanye West’s birthday bash in 2015.
Harden who plays for the Houston Rockets recently opened up about the romance, saying “I [didn’t] like all the attention. I feel like it was for no reason.
I wasn’t getting anything out of it except my name out there and my face out there, and I don’t need that.” The two broke up as Khloe helped Lamar recover from his almost fatal overdose.
Tristan Thompson (2016 – 2018)
Khloe began dating Cavaliers’ basketballer, Tristan Thompson in 2016 after their first appeared at Flo Rida’s birthday party together.
Khloe quickly became pregnant with their first child, True Thompson and mere weeks before giving birth, TMZ broke the story that Tristan had been cheating on the Kardashian with multiple women.
Despite this, they remained together until this year, when news broke that Tristan had cheated on her again, but this time with Kylie’s best friend, Jordyn Woods.
Obviously we’re really jealous of Kylie Jenner. She’s worth a billion dollars and found the love of her life before she was legally able to drink. Does that sound fair? I don’t think so. But, wow we’re still gushing over her relationship
Growing up in the spotlight must be hard, but Kylie landed on the one early on in life and honestly she’s happier than she’s ever been.
Jaden Smith (2013)
This Calabasas teen romance was one for the ages.
Son of Jada and Will Smith, Jaden was locked in a flirty fling with the youngest Jenner sister for a moment or so.
Jaden even attended Kim and Kanye’s wedding, wearing a white Batman suit.
While the two didn’t last very long, Jaden may have been the reason Kylie and Tyga broke up.
“Kylie and Jaden have been hanging out lately and it made Tyga suspicious. He thought something might be going on. So that was one issue,” a source told E! News.
Tyga (2014 – 2016)
Kylie and Tyga’s relationship was controversial, to say the least.
The rapper and beauty mogul’s romance allegedly started when she was just 16, when he was still engaged to the mother of his child, Blac Chyna.
The two made their relationship public when Kylie turned 18 and gifted each other expensive cars and gifts before splitting in 2016.
Following her dramatic split with Tyga, Kylie quickly bounced back with the success of her lip kits and a brief cameo in a rap music video.
But whatever she had with the songwriter didn’t last long.
Travis Scott (2017 – present)
The first time the two were spotted together was in 2017 at Coachella, but since then Travis Scott and Kylie have been inseparable.
Just two months into dating, the couple found out Kylie was pregnant and rolled with the punches.
Since then, Kylie and Travis have made it work, welcoming baby Stormi into their lives and going on tour together while keeping their relationship strong. Ah, young love.
The ultra-private fashion model has had a series of quiet flirtations, but far fewer confirmed romances.
Harry Styles (2013 – 2014)
Kendall Jenner is so full of mystery when it comes to her relationships. She confirms nothing, but then we catch glimpses of her making out with her best friends’ brothers or cheering on some of our favorite basketball players…or our biggest crush from One Direction. Girl’s got game.
Former One Direction member, Harry Styles has been famously private with his dating life, but in 2013 rumors began swirling that he was dating Kendall Jenner.
After sharing a dinner at celebrity hotspot, Craig’s in West Hollywood, the two began being spotted in various vacation spots.
From skiing in Mammoth Mountain to swimming in Anguilla and eventually ending up on Ellen Degeneres’ yacht, things between Styles and Kendall seemed to be heating up.
Khloe even confirmed the two were in fact dating, but as far as relationship labels go, they were a little looser than most. The two reunited briefly at this year’s Met Gala.
A$AP Rocky (2016 – 2017)
While Kendall has always remained tight-lipped about her relationships, when she began dating rapper A$AP Rocky, the model appeared to enjoy the public attention. Attending the Met Gala together, the cute couple looked stunning together.
“It’s the real deal,” a source told Us Weekly, but despite this, they didn’t last very long.
Blake Griffin (2018)
Dating for just six months, Kendall’s relationship with basketball player Blake Griffin was filled with drama and lots of courtside appearances.
After getting caught up in legal troubles with the mother of his child, Brynn Cameron, it seemed that Kendall wasn’t ready for the long-haul and called it quits before anything got too serious.
Ben Simmons (2018 – 2019)
Australian basketball player, Ben Simmons began dating Kendall in 2018 after the two were spotted canoodling in Beverley
Hills. While Simmons was hot off his last relationship, with R&B songstress Tinashe, it didn’t stop Kendall, who was unfazed by Tinashe trashing the two to the paparazzi.
Despite being spotted romantically vacationing in Mexico, Kendall was spotted making out with Anwar Hadid, brother of Gigi and Bella multiple times.
We’re not sure if it was the cheating that drew the relationship to a close but with this much drama, it wasn’t destined to last.