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Ruby Rose's Dating History: Her Most High-Profile Romantic Relationships

Alexandra Lozovschi - Author

Oct. 26 2021, Published 1:54 p.m. ET

While it seems that Ruby Rose is currently single and ready to mingle, the Australian movie, TV and radio star has been the subject of numerous dating rumors along the years, which The List has qualified as "always some of the most interesting."

Although nowadays Ruby's Instagram posts are almost exclusively about her work, one particular update from May sent rumors flying that the Orange Is The New Black and Batwoman alum was courting Riverdale actor Rob Raco.

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The 35-year-old actress, who also boasts a thriving modeling career and has created a net worth of $2 million for herself, is genderfluid and proudly gay and has previously been linked to quite a few famous ladies from the movie and music industry, as well as a slew of models -- Lola Van Vorst (2008), Lyndsey Anne (late '00s), Catherine McNeil (engaged, 2010), Harley Gusman (2016).

Scroll for a timeline of her most high-profile romantic relationships.

2008, 2016-2018: Jessica Origliasso

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Ruby and The Veronicas singer Jessica Origliasso, 36, had an on-again, off-again relationship that first started in 2008. While the ladies rekindled their romance several times throughout the years, they truly got serious about each other in November 2016.

According to Who Australia, it was the "steamy" music video for "On Your Side" that brought them together at the time, which Ruby wrote and directed for The Veronicas in addition to starring in it alongside Jessica.

"We've had such an incredible journey just as friends over the last eight years and then we shot this music video and something changed for us. She's just incredible and I just had to tell her how I felt," said the singer and Cybergirl actress.

Jessica further gushed about Ruby: "I am the luckiest person in the world to be with someone who's the most compassionate, ambitious, strong, beautiful woman."

However, it's no secret that their relationship put a lot of pressure on The Veronicas, with the Aussie musician later revealing it almost broke up the band. Ruby and Jessica announced their split in April 2018, with the Pitch Perfect 3 star tweeting: "I've spent the past two years learning and sharing my life with an amazing human being. An experience for which I am very blessed."

Meanwhile, while on Kyle Sandilands and Jackie O's radio show, Jessica had this to say: "For me, it was time to leave that situation and be as happy and healthy as I deserve to be."

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2014-2015: Phoebe Dahl

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While Ruby's relationship with Jessica was certainly one of her most high-profile romances, her first public and serious love affair was with fashion designer Phoebe Dahl, 32.

The couple began their whirlwind courtship at the start of 2014 and got engaged just three months in, with Ruby revealing she had asked Phoebe to marry her three times before she finally said yes, per People.

“I met Ruby at a barbecue I threw a year and a half ago and we got engaged within about three months. It was all very instant… Honestly, we’re not really apart that often,” Phoebe, who is the granddaughter of author Roald Dahl and the founder of charitable clothing line Faircloth & Supply, said in a later interview.

While everything seemed to be going great, the pair, who announced their engagement in March 2014 and lived together in Ruby's Silver Lake, Los Angeles home, amicably went their separate ways at the end of 2015 due to their conflicting work schedules, after first deciding to put off their wedding until 2016.

“After two wonderful years together, Ruby and I have decided to part ways,” Phoebe told Us Weekly at the time. “While we still love each other and support each other in every way, it is our mutual decision to part ways. Our break is not the result of any media speculation, and we want nothing but the best for each other. Thank you for respecting our privacy in this very difficult time.”

Likewise, Ruby had only good things to say about her ex-fiancée following the breakup.

"Phoebe remains very dear to my heart. I will forever treasure our time together. I’m a better person because of the time we shared. They say, ‘it’s better to have loved and lost than never to have loved at all.’ I’m lucky to have had the chance to love her,” she The Meg actress wrote on Facebook, per Curve magazine.

2015: Halsey (Rumored)

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Days after Ruby and her former fiancée Phoebe called it quits, the XXX: Return of Xander Cage actress was spotted on a day date with Halsey, 27. While the two didn't officially confirm they were an item, and were only seen together a handful of times in December 2015, the media had a field day every time Ruby and the "Without Me" singer stepped out for coffee as a pair.

According to E! News, the duo exchanged flirty tweets as early as August that year, adding to the speculation that they were an item.

2018: Demi Lovato (Rumored)

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Another famous pop star that Ruby has been linked to is Demi Lovato, 29. Just like with her supposed tryst with Halsey, the two didn't openly date, although they did send rumors flying after it was reported they flirted up a storm on Instagram back in 2018.

At the time, Demi commented on Ruby's Fourth of July post, leaving a trio of heart-eyes under a picture of her in a bikini. The John Wick: Chapter 2 actress replied: "Hurry!," and that was enough to send tongues wagging.

Rumors of a romantic entanglement between the two first started surfacing in 2013, while Demi and her long-term boyfriend Wilmer Valderrama, 41, were on a break. It all started with Ruby taking to Instagram to say: “I’m like the one person Demi has slept with that didn’t sell naked photos of her.”

After her post, a source told Life & Style magazine that Ruby and Demi dated for two years while the Disney Channel star and the That '70s Show alum temporarily split.

However, Demi denied she and Ruby ever had a relationship.

"Rumors are rumors, and people are going to spread them. You can believe what you want, but no, I was not in a relationship with her," she told Complex in 2015.


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