Kardashian Breakups and Makeups: A Romantic Rewind

by at .  Updated at .

Some Kardashian and Jenner family members have found true love.

Others are still looking for The One, that diamond in the rough.

As we outline below, however, one thing is certain:

Nearly all these reality star relatives have dated (and sometimes married!) around quite often in their quest for eternal happiness...

1. Damon Thomas

Damon Thomas
It's true! Kim Kardashian was married to this music producer way back in the day! They were wed in 2004 and divorced in 2004.

2. RAY J!

RAY J!
Sorry. We always get excited about him. He dated Kim from 2004-2006 and made a sex tape with her that you may or may not have watched... 129 times.

3. Nick Lachey

Nick Lachey
Yup, before he took Jessica Simpson's virginity, Lachey took a romantic chance on a then-relatively-unknown Kim Kardashian in 2006.

4. Nick Cannon

Nick Cannon
Cannon dated Kim from September 2006 through January 2007 and says the relationship ended because Kim lied about the existence of her sex tape.

5. Reggie Bush

Reggie Bush
Ah, the Bush and the Tush. Kim and Reggie dated from 2007-2010 and it really did seem like the professional running back would be The One. Alas.

6. Kris Humphries

Kris Humphries
The union may have only lasted 72 days, but it did exist. Kim really did marry this professional basketball player in 2011.

7. Kanye West

Kanye West
And then there was Kanye West. It certainly appears as if Kim's journey has finally come to an end, thanks to this father of her two kids.

8. Lamar Odom

Lamar Odom
This is Khloe's one true love. She's on record as saying so. She isn't ashamed of it. But their four-year marriage simply could not survive Odom's cheating and drug use. She finally filed for divorce in the spring of 2016, following many ups and downs.

9. French Montana

French Montana
The rapper was Khloe's first serious boyfriend after things with Lamar went south. They remain good friends to thise day.

10. James Harden

James Harden
While she took time away from Lamar, however, Khloe did have some sex with James Harden. They dated for several months in mid-2015.

11. Adrienne Bailon

Adrienne Bailon
Look how young and cute they were! This singer was Rob's first serious girlfriend. The two were involved from 2007-2009.

12. Blac Chyna

Blac Chyna
Rob isn't known for his dating history. But he appeared to have arrived at the very end of it in 2016, asking Blac Chyna to marry him and putting a baby inside of her womb via his semen. Alas, that relationship ended up being about as rocky as we imagined and then some.

13. Scott Disick

Scott Disick
Incredibly, Kourtney really only dated Scott Disick for most of her adult life. They were together for nine years and have three kids, meaning he got with her at least three times. One would figure she could have done better over a decade or so, but in 2017, it looks like they are never, ever getting back together. Like, Ever.

14. Justin Bieber

Justin Bieber
Okay, fine. Yes, there have been ongoing rumors that Kourtney has at least taken it from Bieber on multiple occasions since she split from Disick in July of 2015.

15. Jaden Smith

Jaden Smith
Kylie and Jaden have always claimed they were friends. But they seemed like a lot more than that for a period in 2013.

16. Cody Simpson

Cody Simpson
Cody definitely dated Kylie in 2012. He was her first real boyfriend.

17. Tyga

Tyga
Kylie dated Tyga for about two years before the stars called it off in the spring of 2016 ... and getting back together and breaking up about 100 more times after that. We really thought these two would make it! (Editor's Note: LOL j/k.)

18. Ryan Nassif

Ryan Nassif
Yup, this is a photo of Kendall kissing Ryan Nassif way back in 2012. He was her first big-time squeeze.

19. Harry Styles

Harry Styles
The singer is pictured here with Kendall. He's really the only famous person she's been associated with since she made it big. It's almost as if Kendall is more focused on building a career than a romantic resume. Crazy, right?

20. Tristan Thompson

Tristan Thompson
Cleveland Cavaliers star Tristan Thompson will pursue a second straight NBA title in June 2017. Khloe will be by his side ... to the abject terror of sports fans in Northeast Ohio.

Wait! There's more! Just click "Next" below:

Next
Show Comments
Stars:
Kim Kardashian, Kourtney Kardashian, Khloe Kardashian, Kendall Jenner, Kylie Jenner, Rob Kardashian
Related Photos:
Kim Kardashian Slideshows, Kourtney Kardashian Slideshows, Khloe Kardashian Slideshows, Kendall Jenner Slideshows, Kylie Jenner Slideshows, Rob Kardashian Slideshows
Related Post:
Created by:
Published:
Modified:

Kim Kardashian Biography

A Kim Kardashian Selfie
Kim Kardashian is the ex-girlfriend of Nick Cannon, Reggie Bush and Ray J. She had intercourse on camera with the former, which is what... More »
Born
Birthplace
Los Angeles, California
Full Name
Kimberly Noel Kardashian

Kim Kardashian Quotes

So far, designing is the most exciting thing I’ve done... I have a vision of what I want [the clothes] to look like in my mind and it’s fun to see it come alive on paper.

Kim Kardashian

He just seemed very firm about the change, and that’s, like, his motto.

Kim Kardashian [on Barack Obama]