Every Kardashian-Jenner Ex-Boyfriend and What They’re Up to Now
Every Kardashian-Jenner Ex-Boyfriend and What They’re Up to Now
Keeping up with what’s going on in the world of the Kardashian-Jenner family is honestly a full-time job—the devil works hard, but Kris Jenner works harder and all that. Keeping up with their litany of ex-boyfriends? Impossible. Even the most well-versed Kardashian nerds among us (aka me) will be shocked to find out that Kylie Jenner dated Cody Simpson and Kim Kardashian once dated Nick Lachey. Here’s who America’s First Family has left in the dust—and what those poor souls are up to now.
Now: Scott Disick
Nowadays, Scott has his own reality show (watch Flip It Like Disick on E! You know you want to!!!!!) and is still going strong with Kylie Jenner’s friend Sofia Richie—ahem, despite their 15-year age difference.
Then: Kourtney Kardashian & Younes Bendjima
This relationship was best described as “permanent vacation mode.” Seriously, name a yacht and Kourtney and Younes probably hung out on it together.
But after a couple years of dating (they first hooked up in 2016), Younes got...well, weird. Not only did he shame Kourtney for showing off her butt in a bikini pic last summer, but TMZ also spotted him cozying up to a woman who was definitely not Kourt in Mexico. They split shortly after because Kourtney doesn’t have time for that nonsense.
Now: Younes Bendjima
Things definitely seem...fine...between Kourtney and Younes. Despite the dramatic split, this dude showed up to his ex’s birthday party in April, that’s all I’m saying.
Then: Kourtney Kardashian & Luka Sabbat
Back in September 2018, the internet lost all chill thanks to reports that Kourtney was “having fun with” actor Luka, who’s almost 20 years younger than her. Excuse me while I take a moment to just be all !!!!!!!
Luka and Kourtney never confirmed their relationship, but in February 2019, he told The Cut, “We’re definitely not dating.” Well, okay then.
Now: Luka Sabbat
These days, Luka is living his best influencer life, starring in Grown-ish, and—ah, yes—still freakin’ hanging out with Kourtney. They were last seen at Kanye West’s Sunday Service in mid-July, just sayin’.
Then: Kim Kardashian & Ray J
Yeah...so Ray J is probably best known as the dude who made a sex tape with Kim in 2003 and then allegedly sold it. Truly, woof.
Now: Ray J
Ray J is still bringing the drama, fear not. Not only did Jordyn Woods just wear his headphones post–Kardashian feud in what was *clearly* shade, but last year, Kim called him a “pathological liar” after he said they had “marathon” sex sessions.
Then: Kim Kardashian & Nick Lachey
Wild, right? Kim and Nick dated in 2006, and then he straight-up tried to claim she used him to make headlines: “Let’s just say this: We went to a movie. No one followed us there. Somehow, mysteriously, when we left, there were 30 photographers waiting outside.”
Now: Nick Lachey
Kim who? Nick is currently married to Vanessa Lachey and they have three gorgeous kids together. Thank u, next.
Then: Kim Kardashian & Nick Cannon
Oh, you didn’t know Kim dated Nick Cannon? Well, time to educate your dang self. They were together from 2006 to 2007 and broke up for the lamest reason: Kim’s sex tape. Basically, Nick thinks she staged its release, telling the Daily Mail: “I still think she might have even had a part to play.”
Now: Nick Cannon
All that currently matters about Nick is that he’s on the greatest show that’s ever been made, the Emmy-deserving The Masked Singer. Also, he ended up marrying Mariah Carey, having twins, divorcing Mariah, and then having another kid with his ex Brittany Bell, but whatever...THE MASKED SINGER IS ALL THAT MATTERS.
Then: Kim Kardashian & Reggie Bush
Reggie was the first boyfriend Kim featured on Keeping Up With the Kardashians, and they dated from 2007 to 2009 before splitting up and eventually getting back together (only to split up again—it was a roller coaster!). The pair ended on good terms, and Reggie recently told Us Weekly, “She’s doing a great job creating a brand for herself, her and her family. I’m happy for ’em….She’s very smart.” Aw.
Now: Reggie Bush
Reggie is married to Lilit Avagyan (who Jennifer Lawrence thinks looks just like Kim) and they have three super cute kids.
Then: Kim Kardashian & Miles Austin
Kim dated football player Miles in 2010 after ending things with Reggie. Apparently, their split wasn’t a result of any major drama, it was simply “their distance apart” that caused things to end.
Now: Miles Austin
Miles married Cowboys cheerleader Stacy Sydlo in 2014, and he’s been keeping things pretty under the radar ever since. Moving on!
Then: Kim Kardashian & Kris Humphries
Hahahahaha. In case you forgot, Kim and Kris were married for an iconic 72 days. Their wedding and breakup was chronicled on KUWTK, naturally.
Now: Kris Humphries
Kris just retired from the NBA and hit back at speculation that his relationship with Kim was fake. In fact, he went so far as to write an entire dang essay about it for the Players Tribune. “There’s definitely a lot about that world that is not entirely real. But our actual relationship was 100% real. When it was clear that it wasn’t working…what can I say? It sucked. It’s never easy to go through the embarrassment of something like that—with your friends, with your family…but when it plays out so publicly, in front of the world, it’s a whole other level. It was brutal,” wrote Mr. Humphries.
Then: Khloé Kardashian & Rashad McCants
On to the next Kardashian sis! Khloé and Rashad dated in 2008 and he’s still bitter about it. Not only did he straight-up accuse Khloé of faking their “breakup scene” for Khloé and Kourtney Take Miami, but he also blamed her for ruining his NBA career, telling the Charlotte Observer, “Without that situation in play, I’m a $60-70 million player. Easily.”
LOL, okay, Rashad!
Now: Rashad McCants
So, uh, the most important update I can find on Rashad’s life is that he’s a major Game of Thrones nerd. Honestly, I don’t hate it.
Then: Khloé Kardashian & Lamar Odom
Woof, what is there to say about Khloé and Lamar? These two got married in 2013 after just a month of dating, so yeah...not exactly a recipe for success. But through it all, Khloé was incredibly loyal to Lamar—even halting their divorce proceedings so she could help take care of him after his overdose in a Nevada brothel.
Now: Lamar Odom
Lamar is doing a lot better. He just released his memoir, Darkness to Light, in which he, uh, revealed some preeetty shocking and awful details about his marriage to Khloé. Exhibit A: He apparently threatened to kill her while he was high on drugs. Read about it over here.
Then: Khloé Kardashian & French Montana
French was Khloé’s rebound relationship after things went south with Lamar in 2014, and honestly, they were pretty cute. But apparently, French was kind of a lot and a “source” (Kris Jenner, is that you?) told E! News that Khloé grew tired of his “needy, obsessive” behavior and “just decided to move on.” Way harsh.
Now: French Montana
Get this: Not only are tabloids reporting that Khloé’s been leaning on French since her split from Tristan “Third Trimester” Thompson (ugh, we’ll get to him in a minute), but they were also legit spotted hanging out at Kourtney’s recent 40th birthday party. The! Plot! Thickens!
Then: Khloé Kardashian & James Harden
Khloé dated James from 2015 to 2016 after meeting him at Kanye’s birthday party, but they split because he cheated on her afterinsisting they become exclusive. Like, who does that?!
“I just don’t want to put up with people that you want to be monogamous but then they’re not monogamous,” KoKo said during Kocktails With Khloé (WOW, R.I.P. TO THAT SHOW). “I’ve always said, ‘It’s long distance.’ I’ve always said, ‘We don’t need to be monogamous! There’s a lot of sh*t going on in our lives. You live in Houston. I live in L.A. Let’s see each other when we see each other.’ 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!”
Now: James Harden
Apparently, James is *still* causing drama for Khloé in 2019 ’cause he was spotted partying in the VIP section of a club with Jordyn (reminder: she cheated with Khloé’s ex Tristan). Jordyn and James are allegedly just friends, but Kylie unfollowed Jordyn just days after their hang sesh, so...??.
Then: Khloé Kardashian & Tristan Thompson
You know, Tristan? Aka the dude who cheated on Khloé when she was nine months pregnant? And then cheated on her again with Kylie’s best friend Jordyn? Yeah. They broke up in February 2019 for reasons that should be filed under “obvious.”
Now: Tristan Thompson
These days, Tristan and Khloé are trying their best to co-parent their daughter, True, and apparently, Tristan just moved 25 minutes away from Khloé in Calabasas to be more involved. He also wished her a super-publicHBD on Instagram, which fully weirded her out.
Then: Kendall Jenner & Harry Styles
Okay, we are officially entering the ~Jenner~ side of the fam. Your boyfriend Harry has been cheating on you with Kendall on and off for years. I know, right? I’ll give you a moment. These two were photographed hooking up on a boat in January 2016 and were most recently spotted leaving the 2019 Met Gala together ??.
Now: Harry Styles
Speaking of the Met Gala, here are Harry’s nipples. Unrelated but important side note: Everyone wants him to play Prince Eric in the new live-action Little Mermaid movie, so now is the time to start an online petition.
Then: Kendall Jenner & A$AP Rocky
Kendall and A$AP Rocky dated in 2016 and even went to the Met Gala. The pair were linked for more than a year, but apparently, they “weren’t really official” and their conflicting schedules led to a low-key breakup.
Now: A$AP Rocky
A$AP was formally charged with assault in Sweden after being detained for allegedly getting into a street fight that was recorded on camera. He was reportedly held in “inhumane” conditions but was just released. Celebrities (as well as Donald Trump) were outspoken about asking Sweden to free him.
Then: Kendall Jenner & Blake Griffin
Did you know Kendall and Blake’s fling broke up his long-term relationship? CUZ IT DID. In July 2017, Blake split from his fiancée (and the mother of his kids), Brynn Cameron—who fully blamed Kendall in child support court docs. No legit, read this:
“Griffin had no problem trading Brynn Cameron, his former fiancée and the mother of his two children, for reality television star Kendall Jenner....Griffin cared more about the glamour of dating a Hollywood celebrity than the day-to-day responsibilities of being a father and family man.”
Guess it wasn’t worth the drama because Kendall and Blake broke up when he moved to Detroit, womp.
Then: Kendall Jenner & Anwar Hadid
This was more of a hookup than a relationship, but the timeline is TEA. Right before Kendall started dating Ben Simmons in June 2018, she was spotted—in the iconic words of TMZ—“sucking face” with Anwar. Then a few months later (while she was fully dating Ben!), Kendall was seen making out with Anwar at a fashion week party. So many questions, not enough answers.
Now: Anwar Hadid
Anwar, man who has no idea what length pants should be, has more than moved on and is now in a relationship with Dua Lipa. Apparently, they have been dating since June 2019 and were seen making out at a music festival, as ya do.
Then: Kendall Jenner & Ben Simmons
The internet realized Kendall and Ben were dating when they were caught cuddling in the background of Khloé’s 4th of July Instagram. They seemed in it to win it but broke up in May—with a source telling People that “the relationship ran its course” and Kendall’s “spending time with her friends and back to being in fun mode.” Cool, love myself some fun mode.
Now: Ben Simmons
Ben is still dealing with Kendall drama. His sister Liv recently popped off on Twitter, calling Kendalla ho who is “working her way through a league.”
Then: Kylie Jenner & Cody Simpson
Yup, Kylie fully dated Cody in 2011 before he was hooking up with Gigi Hadid. Their relationship wasn’t super buzzy, but Cody did briefly chat about Kylie on Hello Ross, saying, “The whole K-O-D-Y thing didn’t work for me.”
Now: Cody Simpson
Unclear who Cody is dating circa 2019, but he and Kylie don’t even follow each other on Instagram.
Then: Kylie Jenner & Jaden Smith
Kylie dated Jaden in 2013 after her short-lived fling with Cody, and she actually met her ex-BFF Jordyn through him. The pair never confirmed their relationship, but it was pretty obvious to anyone with eyeballs.
Now: Jaden Smith
While Kylie and Jaden have maintained their friendship over the years, things seem slightly awkward, considering the Smiths are Jordyn’s closest friends. Jordyn herself was at Jaden’s recent birthday party but Kylie was nowhere to be found, and he doesn’t follow her on Instagram even though she follows him....
Now: Lil Twist
In a life update no one could have predicted, Lil Twist is currently starring on Growing Up Hip Hop. Here for it.
Then: Kylie Jenner & Tyga
LOL, remember when Kylie dated Tyga? The drama! These two were constantly breaking up and making up. To make matters more complicated, Tyga had a kid with Blac Chyna—the same Blac Chyna who went on to have a kid with Rob Kardashian. Kyga finally split for good in April 2017—but not before Kylie got a tattoo of his initial!
Now: Tyga
Even though Tyga tried to take credit for Kylie’s Lip Kits (UGH), the former couple seems like they’re in an okay place. Tyga even shut down an interview question about his ex, saying, “It’s just dating. You date, you move on, you date again, you move on. It’s just a part of life, it’s part of evolving. It’s just learning. There’s no preparation, you just have to learn from mistakes and grow better....I don’t want to talk too much about it. Do you know what I’m saying?”
Then: Kylie Jenner & PartyNextDoor
Sorry for the blurry screen grab, but what we have here is Kylie kissing PartyNextDoor in his music video—which was filmed right after her breakup with Tyga. This relationship was probably just a PR stunt, but either way, Kylie cleared things up during an interview with Complex, saying, “Me and Party have a cool relationship. I think he’s so talented and I love his music. But I wouldn’t say we dated. It never really got to that boyfriend-girlfriend stage. It was just fun. I was doing what I wanted to do.”
Now: PartyNextDoor
PartyNextDoor has new music coming soon, and it *might* feature Rihanna, so get ready.
Wait, Kylie dated Cody Simpson?!