The course of true love never did run smooth. So goes the famous Shakespeare quote, and it’s a sentiment Kim Kardashian can no doubt relate to. The reality TV star and influencer has a complicated dating history – which we’ve seen play out very much in the public eye in real-time thanks to her family’s show, Keeping Up With The Kardashians.

Kim has been married three times. First, she wed music producer Damien Thomas in an impromptu Vegas ceremony, then there was her marriage to NFL player Kris Humphries – which was over in just 72 days and finally, her marriage to music star Kanye West. The pair, who share four children, went their separate ways in 2021.

Despite not finding lasting love, Kim told Jay Shetty during an appearance on his podcast that she’ll “always be a hopeless romantic.”

The SKIMS founder said: “I definitely love sharing my life with someone and love creating a life with someone,” adding that she’s “not lonely” and in no rush to find a new boyfriend.

But what became of her famous exes? Did they manage to find lasting love after being linked to one of the most high-profile women in the world? And what became of their careers?

Damon Thomas

The R&B producer filed for bankruptcy in 2012

Kim Kardashian was just 19 when she eloped with music producer Damon Thomas, whom she married in Las Vegas. He was ten years her senior. On Keeping Up With The Kardashians, Kim regretfully recalled that she didn’t remember most of the 2009 wedding and said the ceremony took place while she was under the effects of ecstasy after trying the class-A drug for the first time.

Damon denied Kim’s claims that she was under the influence when they wed, however, saying in a 2022 interview with Vlad TV: ”That’s a very irresponsible thing to say, given that our children go to the same school.”

Whilst this perhaps wasn’t the fairytale romance, the pair did stay married for three years before filing for divorce in 2003. The 53-year-old music producer went on to have a music career working with big industry names such as Lionel Richie, Chris Brown and Pink. A big career moment was working on the soundtrack of 2006 film Dreamgirls, with My Life earning a Grammy nomination for Best Gospel Performance/Song. Other well-known film soundtracks he has worked on include The Help and Pitch Perfect.

The music producer rarely speaks to the media and little is known about his private life, though it’s believed he has a son, Damon Jr. He has shared photos of his son on his social media over the years, including a post for National son’s Day. In it, he wrote, “Damon Thomas Jr. Your the best son a Dad could ever imagine having. I truly love you to the moon and back.”

Ray J

Ray has settled down with his wife and two children

Musician Ray J and Kim started dating in 2003 after meeting while Kim worked as a stylist for his sister Brandy. They were together for three years, during which time they made the notorious sex tape that was released in 2007, a year after they split.

The tape was a catalyst for Kim’s rise into the public spotlight, but she filed a lawsuit against Vivid Entertainment for distributing it.

Since the couple split, Ray J has talked publicly about his ex and the drama. On Celebrity Big Brother he said he ”loved” Kim at the time. He’s also said, speaking on his podcast Club Shay Shay that since having kids he views his participation in the scandalous film as ”not ok”.

In his professional career, the R&B singer has released five studio albums, appeared on several TV shows and is something of an entrepreneur, being the co-founder of wireless audio brand Raycon and the creator of the electric scooter Scoot-E-Bike.
Years after moving on from Kim, he married Princess Love in 2016, but the pair had a tumultuous relationship – having filed for divorce four times, and requesting to dismiss the filings three times. Ray J shares two kids, Melody and Epik, with his estranged wife.

Nick Lachey

This ex is co-host of popular Netflix show Love is Blind with his wife, Vanessa

Former singer and TV host Nick Lachey had a very brief encounter with the star – they only actually went on one date to the movies together in 2006, after meeting six months post Nick’s split with Jessica Simpson.

Nick’s verdict? ”Couldn’t be a nicer girl, we had a great time,” the presenter said on Watch What Happens Live in 2019 – though he did admit he had suspicions Kim may have called the paparazzi during their date.

Ultimately a repeat encounter wasn’t on the cards, and these days Nick is married to TV host, model and actress Vanessa Lachey (nee Minnillo). The pair share two sons and a daughter.

Nick, 45, has carved out a successful career, co-hosting some of Netflix’s top romance reality series Love Is Blind, The Ultimatum: Marry or Move On with his wife. Aside from presenting, he has made guest appearances on Dancing With The Stars, Taking The Stage and won season five of The Masked Singer.

Nick Cannon

Kim ”broke” ex-boyfriend Nick’s heart in 2007

Nick Cannon said he was devastated after the end of his brief one-year fling with Kim in 2007. Reflecting on thei romance during an interview with Drink Champs in 2021, he said: ”She broke my heart.” There were no hard feelings though.

These days he’s perhaps best known for hosting The Masked Singer, but in the earlier days of his career he was a regular Nickelodeon Awards presenter and created TeenNick series The Nightlife. Another huge presenting gig for him was America’s Got Talent before he resigned in 2016 due to creative differences between him and NBC. He created his own daytime talk show The Nick Cannon Show, however this was cancelled after one season in 2022.

Reggie Bush

He now works as a football analyst

‘The one that got away’ for Kim was former American footballer Reggie Bush, who Kim dated from 2007 to 2010. Faced with long-distance challenges, the pair’s relationship didn’t work because of Reggie’s commitments in the NFL season.

After they split Reggie settled down with choreographer Lilit Avagyan The couple wed in 2014, and a decade later, they have three children: Briseis, Uriah and Agyeman.
Reggie’s sport career has since crossed over into the technical aspects of the game – the 36-year-old now works as a football analyst for Fox Sports.

Miles Austin

The NFL star became a coach and married his college sweetheart

The NFL star became a coach and married his college sweetheart

Another long-distance relationship which didn’t go the distance was Dallas Cowboy Miles Austin’s brief romance with Kim in 2010.

Kim was spotted on the sidelines of his games during the summer that year and the pair were spotted on double dates with the other Kardashian sisters, but ultimately they split in September.

After Kiki, the football coach continued to play for the NFL league but retired due to hamstring issues in 2013. After a stint playing as a free agent, he became a coach, working for teams including the New York Jets and San Francisco 49ers.

He ended up marrying his college sweetheart Stacey Sudlo in 2014 and the pair share three children together; Miles IV, Ava and Max.

Kris Humphries

Kris has said that their relationship was ‘100% real’

NBA player Kris Humphries and Kim’s relationship was the very definition of a whirlwind romance – the pair got engaged just six months after they started dating. After their marriage became a two-part TV special, Kim filed for divorce 72 days later, proclaiming in a statement that ”sometimes things don’t work out as planned”.

After they split, Kris disappeared from screens on Keeping Up With The Kardashians and returned to his life as a professional basketball player. He played for a wide range of teams including Utah Jazz, Dallas Mavericks and New Jersey/Brooklyn Nets until he retired in 2019.

A look at the sportsman’s Instagram reveals he has gone into the restaurant business, opening four Dave’s Hot Chicken eateries in Minesota.

His personal life has stayed out of the press, and if the 39-year-old former athlete is currently dating anyone, he’s kept the relationship completely out of the public eye. He commented on his relationship with Kim in his 2019 Players’ Tribune essay, saying that their relationship was ”100% real” and that the public downfall of the relationship for him felt ”brutal.”

Kanye West

Kanye is due to release his third collaborative album later this year

Kim and Kanye West’s marriage came to an end when she filed for divorce in 2021 after a rocky period in their relationship.

Their marriage first seemed to hit the rocks in 2020 when Kanye announced his presidential campaign – and revealed deeply personal details about his family and marriage. Kim had also asked fans for “compassion” as her husband dealt with mental health issues.

The former power couple had four children, North, Saint, Chicago and Psalm during their ten-year relationship, with this being Kim’s longest romance.

“If people knew what my relationship really was like, I think they would be like, ‘How did this last this long?’ But I can live with myself knowing that I tried everything humanly possible to make a situation work and so I can walk away feeling absolutely guilt-free,” Kim said during an episode of The Kardashians.

Winning 24 Grammys during his career, the 47-year-old has continued releasing records since the split. His latest collaborative album, Vultures is being released as a trilogy with the third release scheduled for later this year.

The rapper is currently involved in a lawsuit involving his former employee Lauren Piscottia. A complaint was filed in June 2024 against Kanye including reports of unpaid wages; this was denied by his legal representatives. In October, the complaint was amended to accuse the singer of sexual assault. Kanye has not commented on these new allegations.

Pete Davidson

Pete has been absent from the latest Saturday Night Live season

In 2022, comedian Pete Davidson and Kim parted ways due to their busy schedules after a brief nine months together. They started hanging out after Kim played Princess Jasmine opposite Pete’s Aladdin in a skit on Saturday Night Live.

SNL star Pete has been off the radar for a while and has been absent for the start of the show’s 50th season amidst reports of a feud between him and his former co-host Colin Jost.

After dating a Kardashian, Pete has been linked to several other high profile actresses and celebrities. Among them Emily Ratajkowski, Bridgerton’s Phoebe Dynevor, Cindy Crawford’s daughter Kaia Gerber, Ariana Grande and model Emily Ratajkowski.

Odell Beckham Jr.

He plays for the NFL team Miami Dolphins

Kim’s most recent split was from NFL player Odell Beckham Jr – who she privately dated for seven months. According to Entertainment Tonight, the pair remained friends and the split was mainly due to Kim’s desire to concentrate on being a hands-on mom.

The Superbowl champion is busy too – he’s back on the field with the Miami Dolphins after mising the start of the season due to an injury.

The sportsman was previously linked to model Lauren Wood from 2019 to 2023 and they share a two-year-old son named Zyn.

BY IONA MACROBERT