A Look At All The Women Rob Kardashian Has Dated

Highlights

Rob Kardashian’s love life has always been heavily scrutinized, whether on TV or in tabloids, due to his high-profile romances.
From Adrienne Bailon to Rihanna, Rob’s relationships have been messy and public, leading to breakups and drama over the years.
Despite past relationships, Rob seems to be focusing on co-parenting his daughter Dream and keeping a low profile in the public eye.

Rob Kardashian is known for keeping a low profile. He was a main cast member when Keeping Up With the Kardashians aired in 2007, but struggles with his weight had fans seeing less of Rob on TV. He’s become a rarity on The Kardashians and has been focusing on privately raising his daughter, Dream.

Still, whether Rob ever chooses to go back to reality TV, his love life has always been a hot topic of conversation. Some of his very first romances were highlighted on KUWTK. And, even if they weren’t shown on television, Rob’s personal relationships have constantly been written about in the tabloids. Let’s take a look at all of his high-profiled romances that we know of.

2:07

A Look At Kourtney Kardashian Barker’s Relationship History

Kourtney Kardashain Barker’s relationship history isn’t as extensive as her sisters, but it involves a handful of high-profiled men.

7 Adrienne Bailon

Alleged Dating Timeline: 2007-2009

Rob Kardashian’s relationship with Cheetah Girl’s singer Adrienne Bailon debuted on Season 2 of Keeping Up With the Kardashians. In one episode, Rob shockingly revealed that he got his girlfriend’s name tattooed on his body. Their relationship further played out in Season 3, in which they ultimately broke up after Rob had cheated on her.

Us Weekly reported on Rob’s love life and shared that Adrienne had no ill-will towards her ex when talking on an episode of The Real in 2016. She admitted, “We’ve come such a long way. I think Rob is a great guy … What’s in the past is in the past.” In fact, Adrienne remains a good friend with the Kardashians to this day.

6 Angela Simmons

Alleged Dating Timeline: 2010

Right after his split with Adrienne, Us Weekly reported that Rob entered into a relationship with Angela Simmons, which was short-lived. The daughter of record executive Russell Simmons, Rob and Angela’s alleged romance occurred in 2010 for a few months.

During a red carpet interview in April 2010, Angela seemingly confirmed her relationship with Rob when a reporter asked her if she was dating the reality star. “Right now I’m talking, and I have friends, and you know, I’m chilling, I’m happy.”

Kylie Jenner And Timothee Chalamet Avoid Marriage Rumors After He Skipped The Kardashians Finale

Kylie Jenner and Timothée Chalamet fuel marriage rumors as he skips The Kardashians finale, keeping fans guessing about their future.

5 Rita Ora

Alleged Dating Timeline: 2012

Rob’s relationship with singer Rita Ora was extremely messy and it all played out in public. The pair entered into a relationship sometime in 2012, but just two months later, Rob took to X to claim that Rita had cheated on him with several men, as Us Weekly reported.

“How can a woman who is so busy trying to start her own career have time to be with so many dudes all while in a relationship. I’m actually disgusted a woman could give up her body to more than 20 dudes in less than a year’s time while trying to start a career.”

The relationship would mean nothing to Rita years later. In 2020, when asked by The Sunday Times about her romance with Rob, Rita shared, “Oh, I forgot about that.”

4 Rihanna

Alleged Dating Timeline: August 2010-Fall 2010

Rihanna in front of the paparazzi — Via: Deposit Photos

Fans may have forgotten that Rob and Rihanna had a “thing” after his dramatic split from Rita Ora. They were spotted in the summer of 2012 going go-karting in California and later partying the night away that same day, as Us Weekly noted.

Although neither Rob nor Rihanna have publicly spoken out about their time together, E! News reported that the reality star told Ryan Seacrest in a radio interview that they were just friends.

“It’s because Rihanna’s a friend, and she is friends with my friend Capricorn, and it was Cap’s birthday. We all went out to celebrate our friend’s birthady. It was fun. It was a good night,” Rob said.

Us Weekly reported that his fun-filled adventures with Rihanna ended around the fall of that year.

3 Blac Chyna

Alleged Dating Timeline: January 2016, Engaged April 2016-Early 2017

Blac Chyna and Rob Kardashian before their split — Via: Instar

In January 2016, Rob and Blac Chyna revealed that they were dating. It was an extremely odd pairing at the time because Rob’s sister, Kylie Jenner, was dating Blac Chyna’s ex and father of her child, rapper Tyga. Despite this, everyone seems to be on good terms with the entire situation.

Between his flirtatious dates with Rihanna and his more serious romance with Blac Chyna, Rob dated British singer Naza Jafarian for a short period of time.

The couple had a whirlwind romance. As Us Weekly reported, that April, they announced their engagement, and the following month, shared that Blac Chyna was expecting a child with Rob. Their daughter, Dream, was born in November, but the couple called it quits in early 2017.

The exes feuded soon after, and a nasty child support battle ensued. Even Tyga got into it as Blac Chyna blasted both men for not coughing up child support. In 2020, Blac Chyna and Rob were granted joint custody of their daughter Dream.

All Of Rob Kardashian’s Past Girlfriend’s Birthdays	Age As Of 2024
Robert Kardashian Jr. – March 17, 1987	37
Adrienne Bailon – October 24, 1983	40
Angela Simmon – September 19, 1987	36
Rita Ora – November 26, 1990	33
Rihanna – February 20, 1988	36
Blac Chyna – May 11, 1988	36
Alexis Skyy – July 14, 1994	30
Natti Natasha – December 10, 1986	37

In August 2023, Blac Chyna shared an update with ET on where she, Rob, and Tyga, stood when it came to co-parenting their kids. The model made it clear that, despite any tension, her children are the most important. “I feel like with everything – time heals everything, and people change, and situations change, and you get to see the situation for what it is, and the situation is Dream.”

Scott Disick’s Weight Loss On The Kardashians Follows A Doctor Calling Him ‘Malnourished’

Scott Disick’s shocking weight loss revelations come after a doctor publicly worried about his health.

2 Alexis Skyy

Alleged Dating Timeline: January 2019

Rob Kardashian appeared to have a major crush on Alexis Skyy and wasn’t shy to let the world know. As Us Weekly reported, in January 2019, he took to Snapchat where he shared that the Love & Hip Hop star was his “WCW” (Women Crush Wednesday). However, this came just days after Alexis got into a heated altercation with Blac Chyna at an event. So, was Rob just trying to get back at his ex?

It’s not clear how serious Rob and Alexis were. However, he did invite her to his mom’s, Kris Jenner’s house for a dinner date shortly after announcing the reality star as his Wednesday crush.

1 Natti Natasha

Alleged Dating Timeline: June 2019

Dominican singer Natti Natasha and Rob sparked relationship rumors in June 2019. After Rob shared a photo of him with his daughter, Dream, on his shoulders, wishing a Happy Father’s Day to himself on X, the singer reposted it, and wrote, “Happy father’s day! You are an excellent father, I know. God bless you. See you soon!”

According to Us Weekly, Rob responded to Natti by telling her he would see her soon, which caught Khloe Kardashian’s attention. The Good American founder replied to her brother’s post with, “Rob what’s going on here?!?! Who is this girl?”

There’s no clarification about whether Natti and Rob had a romantic relationship, but their social media exchange did give off flirtatious vibes.

Nowadays, it seems like Rob is mainly focused on his daughter, Dream.