Rob Kardashian is a part of reality TV royalty, and although fans got to know him through the show, in recent years, Rob has opted to stay out of the limelight. He leads a quiet, reclusive life, and it’s become almost impossible to spot him doing anything, let alone going on holiday.

But that wasn’t always the way Rob wanted to live his life, and over the years, he's had some very high-profile relationships with big stars like Rita Ora and Adrienne Bailon.

Rob also wasn’t afraid to do things, and traveled the globe for his international romances, attending local events and visiting hotspots. Below are 20 photos of some of the most attractive women Rob Kardashian has enjoyed spending time with when he gets a break from his busy schedule.

20 Rob Kardashian And Rita Ora Were Spotted Leaving A Party In London

Although Rob and Rita Ora's relationship didn’t last long, and their breakup was ridiculously public, during their time together, they were seen in London. In fact, according to The Sun (via Daily Mail), the distance may have been what caused their split, with Ora based in London and Kardashian in Los Angeles.

19 One Of His First High-Profile Relationships Was With Adrienne Bailon, And They Went On Several Adventures Together...

Rob Kardashian and former Disney star, Adrienne Bailon, had a high-profile romance. According to Us Weekly, the former couple dated from 2007 to 2009, with Bailon describing the coupling as “the shortest relationship I’ve ever had.” Despite only being together for two years, the pair were photographed together on several adventures.

18 ...Including Visiting An Amusement Park With Rob's Little Sisters, Kendall And Kylie Jenner

One of the experiences that Rob Kardashian and Adrienne Bailon went on was to an amusement park with his little sisters, Kendall and Kylie Jenner. Although the relationship with Rob didn’t work out, Bailon remains on good terms with the rest of the Kardashian clan, telling Us Weekly, they are all “fun people.”

17 Rob’s Been A Bit Of A Recluse In Recent Years, But Blac Chyna Was Able To Get Him Out

Rob Kardashian prefers to live away from the public eye. Fans rarely get a glimpse of Kardashian, and he’s not active on social media, but there was a time when Blac Chyna changed that. When the pair started dating, Kardashian was seen in public more often, including attending a Las Vegas pool party, TMZ notes.

16 They Even Took A Memorable Trip To Disneyland!

During their relationship, Rob Kardashian and Blac Chyna also visited Disneyland! Chyna’s son, King Cairo, accompanied the couple on the trip. According to People, Chyna documented their little getaway on social media and posed happily for many photos with Kardashian and her son. They appeared to have a great time, despite the rain.

15 There Was A Time When Rob Kardashian Attended Events Like Coachella

It’s hard to see Rob Kardashian doing anything these days, let alone attending public events, but there was a time when he could be seen at popular hotspots. He didn’t think twice about going on trips and being photographed, and according to Zimbio, Kardashian attended Coachella Valley Music and Arts Festival with Adrienne Bailon.

14 He Jetsetted Everywhere With GF Naza Jafarian

Another woman who Rob Kardashian has been linked to is Naza Jafarian. According to HollywoodLife, Jafarian lived “mainly in London,” but the pair still managed to find time to spend together. “They spent St. Patty’s day together in L.A, and now she flew to London with him!” an insider told the publication at the time of their relationship.

13 Rob Went Out On Several International Dates With Naza Including A Club In Knightsbridge

As mentioned, Naza Jafarian didn’t live in Los Angeles where Rob Kardashian was based, so some of their dates were international. In 2013, when they were believed to be dating, the pair were seen heading into The Wellington Club in Knightsbridge, Daily Mail notes. Interestingly, momager Kris Jenner was also in the country during this time.

12 We Can’t Forget That He Has Beautiful Sisters And They've Gone On Several Family Trips!

What list about the most attractive women that Rob Kardashian has been on vacation with, would be complete without a mention of his sisters?! Recently, Kylie Jenner posted a photo of herself, Kendall Jenner, and Rob, hanging out, and she captioned the sweet pic with the following message: “5 am birthday adventures with my two fav people.”

11 Rob Looked So Happy Dancing With Kim In The Dominican Republic

One of the family holidays that Rob Kardashian went on was to The Dominican Republic, and the vacation was filmed for their reality TV show, Keeping Up with the Kardashians.

“On our last night there, we had a fun dance party,” Kim said, according to Perez Hilton. “Of course, I had the best dance partner ever, my brother, Rob!”

10 And He Spent Time On The Water With His Baby Sister Kendall Jenner

Rob Kardashian has also been spotted enjoying a boat trip on the ocean with his sister Kendall. The two siblings are close, and when Rob surprised Kendall for her birthday in 2019, by making a public appearance at a club (via People), she was extremely grateful. “Best bday present ever,” Jenner said of her brother’s attendance.

9 Nothing Like A Little Trip To Miami For A Birthday Celebration, Right?!

It seems birthdays are special to the women in Rob Kardashian’s life, and he has made an effort to make them memorable. When he was dating Blac Chyna, the pair found time in their busy schedules to enjoy a “quick getaway to Miami” for Chyna’s birthday, E! News reports.

8 He Also Accompanied His Mama And Kim To A Club In Las Vegas

Rob Kardashian may celebrate his birthdays away from the public eye now, but this wasn’t always the case. In 2012, he made an appearance at the 1 OAK Nightclub at The Mirage in Las Vegas, where his mom, Kris Jenner joined him, and sister Km Kardashian, Vegas News reports.

7 Ah, A Wonderful Beach Stroll With The (Former) Love Of His Life

Blac Chyna and Rob Kardashian had some adorable moments during their relationship and were often spotted out together. She even managed to get the reclusive star on a beach! According to Us Weekly, this outing was one of Kardashian’s first in years, and he went to show his support for Chyna’s beach photoshoot in Los Angeles.

6 Angela Simmons Even Managed To Get Rob To Go For A Trip To The Nail Salon

After Rob Kardashian and Adrienne Bailon split, he was linked to Angela Simmons. According to Us Weekly, the pair had a “fling” for a few months in 2010. During their relationship, they were spotted together in public a few times, including attending a Lakers game and having pedicures!

5 The Pair Also Celebrated A Birthday Together At A Fancy Hotel

Rob Kardashian and Angelina Simmons were also seen in 2010 as they left a fancy birthday event. It wasn’t either one of their birthdays though; instead, it was the E! 20th Birthday Celebration at The London Hotel, Zimbio reports. The hotel is located in West Hollywood, California.

4 Blac And Rob Were Spotted At Los Angeles International Airport After A Little Trip

Rob Kardashian and Blac Chyna did a lot together (and we don’t just mean they got engaged and had a baby), but much of their time was also dedicated to their various work commitments. The duo was seen hanging out in Los Angeles International airport while they waited to jet off to their next destination.

3 Although They Didn't Have Loads Of Exotic Holidays, Rob And Blac Chyna Took Low-Key Trips Like An Outing To The Movies

Although the former couple spent time jetting from one destination to the next, they didn’t need to go far from home to enjoy quality time together. Among their outings that were closer to home, was a low-key trip to the movies at the Arclight Cinema in Sherman Oaks, Daily Mail notes.

2 Rob Showed Off His Dancing Skills With Cheryl Burke, But They Also Spent Time Together Outside Of Rehearsals

Rob Kardashian is a skilled dancer and appeared on Dancing with the Stars, where he was partnered with professional dancer Cheryl Burke. The pair spent a lot of time together in rehearsals, but also hung out together at press launches and events including the iHeartRadio Music Festival and Macy's Ideology launch.

1 Before Rob Decided To Hide From The Public, He Was Going To Clubs Like Hyde Lounge In Los Angeles With His GF (And Sisters)

Fans of Rob Kardashian get excited every time he remerges from hiding, but there was a time when he was very confident and comfortable in public. He also didn’t mind who saw him and looked super happy at the Hyde Lounge with Adrienne Bailon and his sisters, Zimbio notes.