Since stepping into the spotlight 20 years ago, Kim Kardashian has had a range of boyfriends.
Rappers, comedians, music producers, NFL players. You name it, Kim has dated them.
While the second-eldest Kardashian sister has been present in social circles since the early 2000s, when she was often pictured with the likes of Paris Hilton, most people know the socialite from Keeping Up With the Kardashians (KUWTK) and later, The Kardashians.
Her work in the entertainment industry brought her face-to-face with everything from athletes to music executives, some of which she went on to date.
Despite dating a range of interesting people, Kim is undoubtedly most known for her marriage to Kanye West, which lasted six years and bore four kids.
After Kanye came Pete Davidson, but there’s a whole host of noteworthy people who have become seemingly lost to relationship history. Let’s take a look.
Damon Thomas
Songwriter and music producer Damon Thomas, 29 at the time, eloped with Kim when she was just 19 years old. Boasting a net worth of $1 million, Damon was most known for his work with artists like Lionel Richie, Omarion, and J. Valentine.
Kim and Damon were married for three years until their relationship met an untimely demise in 2003, with Kim later claiming that she was on drugs at the time of the nuptials.
Ray J
One of Kim Kardashian’s more prominent boyfriends was rapper and singer William Ray Norwood Jr., known professionally as Ray J, who has quite a dating history of his own.
The two lovebirds met when Kim was doing styling work for Ray J’s sister, Brandy.
Ray J and Kim Kardashian dated from 2003 to 2006, but the relationship has continued to hit the headlines to this day following the release of a 2007 sex tape featuring the two celebrities.
Though Kim has seemingly moved on from the ordeal, again attributing the lapse in judgment to drugs, Ray J has continued to offer comments over the years, much to Kim’s annoyance.
Nick Lachey
In 2006, shortly after splitting from Ray J, Kim hitched herself with TV host and actor Nick Lachey, who had recently separated from Jessica Simpson.
The couple only went on one date, with the Love Is Blind host now happily married to Vanessa, former Miss Teen USA. The happy couple now have three kids together, Camden, Brooklyn, and Phoenix.
Nick Cannon
Nick Cannon, who fans now know has more kids than bedrooms at home, dated the reality TV sensation from 2006 to 2007 after first meeting her while she was still with Ray J.
Despite the relationship being relatively short-lived, Nick remembered it kindly in a 2014 radio interview: “She’s a great girl though! Her and her family are some of the most incredible people I’ve ever met in my life.”
Reggie Bush
While Kim Kardashian’s dating history is predominantly documented by scandalous headlines and social media finds, that was not the case when it came to football player Reggie Bush.
Their relationship featured heavily on KUWTK, where Kim said he could be “the one.”
Unfortunately, most of Reggie’s time was spent with the New Orleans Saints and away from Kim in Los Angeles.
Despite splitting up and coming back together in 2009, Kim and Reggie finally called it quits in 2011, citing time management and the distance as the cause.
Miles Austin
Kim’s dalliance with Reggie clearly sparked a love of football players as she soon engaged in a relationship with Dallas Cowboys frontman Miles Austin.
On more than one occasion, Miles was spotted with Kim and her sisters, Khloe and Kourtney Kardashian.
Though they first agreed on balancing their busy work schedules, the long-distance element again torpedoed the relationship’s progression.
Gabriel Aubry
By 2010, Kim Kardashian had moved on from football players to fill her dating history ranks with men of a different breed.
In this case, that breed was Halle Berry’s ex, Gabriel Aubry, who is said to have enjoyed Thanksgiving dinner with Kim, Kris Jenner, and the rest of the Kardashian clan.
By the end of the year though, Gabriel had joined the ranks of Kim Kardashian’s ex-boyfriends.
Kris Humphries
Kim jumped back into the athlete dating pool with basketball player Kris Humphries in 2010.
The whirlwind romance culminated in a shock proposal in 2011, with the two getting hitched at a private home in Montecito, California, for the world to see on KUWTK.
Just 72 days after saying “I do”, Kim announced that she had filed for divorce. The car crash marriage has since been compared to the tenure of former UK Prime Minister, Liz Truss.
“I hope everyone understands this was not an easy decision. I had hoped this marriage was forever, but sometimes things don’t work out as planned. We remain friends and wish each other the best,” she said in a statement.
Kanye West
Kim’s most iconic relationship is undoubtedly with controversial rapper-turned-fashion designer, Kanye West.
While Kim and Kanye had crossed paths over the years, with the latter taking issue with her marriage to Kris Humphries, they did not officially get together until 2011.
Come 2012, Kim was pregnant with their first child, North West, who was born in 2013. The momentous occasion was soon followed by a wedding, followed by more kids: Saint, Chicago, and Psalm.
Their relationship dived in 2020, with some attributing that dip to Kanye’s sudden Presidential campaign and numerous public outbursts related to his diagnosed bipolar disorder. In 2021, the world was changed forever when Kim filed for divorce.
Though the exes have had a tumultuous relationship since the divorce, with both taking jabs at each other over the internet, they did put differences aside for North West’s recent Lion King debut. Still, Kanye is undoubtedly one of Kim’s more controversial boyfriends.
The rapper is now married to architect and model Bianca Censori, who is often compared to Kim.
Pete Davidson
After the disintegration of her relationship with Kanye, Kim surprised everyone with her new boyfriend, comedian Pete Davidson.
Besides his work on Saturday Night Live, he was most known for his relationship with Ariana Grande.
Kim and Pete reportedly met on the set of SNL before making their red carpet debut during a 2022 White House event.
Though some were admittedly confused by the pairing, fans loved his obvious glow-up and touching details like his tattoo in her honor. Reality TV lovers also loved how he handled the feud with Kanye.
Despite being one of Kim Kardashian’s more popular boyfriends, the couple called it quits in July 2022. At the time, and while admitting that they had fun together, Kim and Pete said the relationship had “run its course.”
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