Inside Ruby Rose's Love Life

Long before Ruby Rose pulled out of the CW's Batwoman or rose to fame in America with her breakout role in Orange Is the New Black, she had a storied career down under as an MTV VJ. In other words: she's been a celeb for quite a while, right under the noses of those of us stateside. This also means that she has an entire celebrity dating history we don't know much about — and it involves an inordinate number of alleged engagements. Don't worry though, New Jersey Housewife Danielle Staub still takes the non-wedding cake with 21. Nonetheless, when Rose falls, she falls hard.

Throughout her career, Rose has always fought for LGBTQ+ visibility, because it's something she didn't have as a kid. In an interview with Today, the star revealed that she came out to her mom when she was 12 years old, but didn't really know how to go about it. "I was just worried because ... I didn't know it was a thing," Rose said, adding, "I knew how I felt, I knew what I kind of identified as, but the words gay or lesbian, I didn't know anyone else who was gay or lesbian."

Since then, Rose made history as the first "openly gay superhero lead in a TV role," according to The Washington Post. She's also filtered in and out of a number of highly public relationships — from summer flings to steamy alleged love triangles.

If there's one thing Ruby Rose is clear about, it's that she doesn't really care about marriage — at least not in the sense of a holy sacrament or relationship milestone. The actress cares about equality, which might make her numerous reported engagements a powerfully rebellious statement against her home country of Australia, which only legalized same-sex marriage in 2017, according to The New York Times. Since the legislation passed, Rose hasn't gotten down on one knee again. Her last engagement ended in 2015, according to People, and it doesn't seem like she's really focused on tying the knot.

In a 2017 interview with Cosmopolitan, Rose admitted, "For me, marriage is more about equal rights than the act of getting married. When you don't have equal rights, it trickles down to kids who think, 'My aunt's gay so she can't get married, or I'm weird because I feel the same way.' So it's important to break down that barrier."

The actress also revealed that she's doesn't care as much about the paperwork as she does about the idea of family. She's not searching for a bride. Instead, Rose is focused on developing a "loving, healthy" relationship with someone she "might want to have kids with."

Before Ruby Rose launched her career in the United States, she found herself embroiled in a model love triangle. The common thread was Australia's Next Top Model, where Rose had a two-time guest judging gig in 2009. It's hard not to notice that 2009 was quite the year for the star. According to The West Australian, that's when she landed her MTV VJing gig, which made her a household name in Australia. On top of that, she reportedly almost tied the knot, though she never quite made it down the aisle.

It all started when Rose became romantically involved with Chadwicks model Lyndsey Anne McMillan, per The Daily Telegraph. The main issue was that McMillan was already dating former Australia's Next Top Model contestant Lola Van Vorst. The pair had reportedly been together for a few months, but McMillan apparently ditched her to start dating Rose. The breakup was reportedly "intense," and the three of them allegedly crossed awkward paths at the Bonds Spring/Summer 2009 Fashion Launch. That's where McMillan told The Daily Telegraph that the event's DJ was her girlfriend. Rose was the woman behind the turntables.

According to The West Australian, Rose and McMillan got engaged later that year, but it was short-lived.

Ruby Rose's relationship with Lyndsey Anne McMillan didn't even last a year ... and the reason might have been the star's unwillingness to appear on reality TV. It's a little hard to believe considering the actress got her start on MTV, but apparently, the couple's alleged engagement was shattered by McMillian's lofty — and highly public — career ambitions.

According to The Daily Telegraph, things started crumbling when McMillan "went against Ruby's wishes" and started shooting a pilot for Summer City, a reality show more akin to The Hills than the 1977 Mel Gibson-led Australian thriller of the same name. A source told the newspaper, "The last thing that Ruby wanted was a crew following them around with cameras with the focus on their private lives, but Lynds went ahead and did it anyway."

During this time, Rose was reportedly trying to craft a family friendly image as the host of The Ultimate School Musical: Fame, which had a younger audience. Things allegedly came to a head when McMillan visited a sex shop with her ex, Lola Van Vorst, and tweeted about it. Rose apparently urged the pair to remove their tweets, but Twitter is fast. Fans already saw them. We can only assume they were screenshotted into oblivion.

Per The Daily Telegraph's report, the pair had rumored plans to tie the knot in Canada despite only jumping into a relationship a couple months prior. Those plans were shattered, and Rose was onto the next.

If you can't beat 'em, join 'em. That's exactly what Ruby Rose did with supermodel Catherine McNeil. According to BuzzFeed, the Batwoman actress got her start in Girlfriend's 2003 model search, which she lost to McNeil. Years later, amidst her split from Lyndsey Anne McMillan, The Daily Telegraph reported that she reunited with her former competitor, and the pair started getting cozy in "various venues around town." To be clear, they never confirmed or denied their relationship. This was a total no comment situation, but at the start of 2010, it looked like things were getting serious, and the pair reportedly rang in the New Year as a newly engaged couple.

According to a source who spoke to The Sunday Telegraph, Rose and McNeil got engaged right before Christmas. Rose had spent the holidays with McNeil's family in Logan, Queensland and reportedly changed her Facebook relationship status to "engaged." The couple then shipped off to Melbourne, where they celebrated New Years Eve and reportedly hosted a small engagement dinner to share the news with their friends. 

Days later, Rose publicly announced the news on Facebook with some photos of their loved-up holiday on the Gold Coast. "So in love can't wait to spend the rest of my life with u baby," Rose wrote in the announcement (via The Sunday Telegraph). At the time, same-sex marriage wasn't legally recognized in Australia, so the couple reportedly planned to wed in Canada.

Ruby Rose and Catherine McNeil may have had the star power of two women who dominated Girlfriend's model search, but the pair's bond wasn't strong enough to withstand the distance. By the summer of 2010 — just a handful of months after they got engaged — they called the whole thing off.

According to News.com.au, distance contributed to their split. Rose lived in Australia, and McNeil lived in New York City, which is 14 hours ahead of the Batwoman star's hometown of Melbourne. The actress didn't move stateside until 2013. "It's sad they've broken up and both women are determined to remain close but the relationship wasn't working," a source told the outlet. May they always have the paparazzi photos and McNeil's "RR" tattoo for posterity.

McNeil was notably torn up about the broken engagement. In an interview with WHO magazine (via Digital Spy), she admitted that she had to "take a step back" from modeling. "I had this growing sense of losing myself, and I needed the time to breathe and find my own voice," she said. "I started modelling young ... But once I left home I needed to act like an adult, and I wasn't one."

Despite the breakup, it looks like both women were able to maintain their long-standing friendship. In 2019, the Orange Is the New Black actress called McNeil her "favorite person" in an Instagram birthday tribute, according to the Daily Mail.

About a year after Ruby Rose's split from Catherine McNeil, the actress was already reportedly engaged to someone new: fashion journalist Lia-Belle King. According to The Daily Telegraph, the couple met on the set of a photo shoot in May 2011. Rose apparently "wooed" the writer by sending her flowers. Hey, that move has a proven track record. It even worked to temporarily smooth over Taylor Swift and Kanye West's epic feud, which is, by all accounts, a herculean feat. 

At the time, The Daily Telegraph hailed them "Sydney's lesbian 'it' couple" — and honestly, it's not a wild claim considering Rose was a Miu Miu brand ambassador and King was a fashion writer for InStyle. That year, the pair even went on an "all-expenses-paid" trip to China, where they sat front row at Prada's A/W 2011-2012 show and showed off their matching engagement rings.

Like Rose's past engagements, this one didn't last either. In 2014, she moved on to clothing designer Phoebe Dahl, Roald Dahl's granddaughter.

In 2014, Ruby Rose went to a BBQ, but only with the pretense that she was going to meet someone's pet pig. Instead, she ended up meeting her fourth fiancée (and probably her fiancée's pet pig, too). That someone was Phoebe Dahl, who was immediately struck by the model ... even though she was already in a relationship. "The second I saw Ruby, I completely fell for her. It sounds corny, but it was love at first sight," Dahl told Out in 2015. "Apparently, she felt the same thing."

According to People, Rose asked for Dahl's hand in marriage four times before the designer said yes on the final attempt. Dahl told Out that the first proposal came before Rose even said "I love you." Though they got engaged a speedy three months into their relationship, the pair did wait on their wedding. In 2015, Rose told People that she unexpectedly got really busy after Orange Is the New Black (people really liked her role!), and Dahl's family was too big to just run away and elope. She also planned to wear a tux, which was sadly never rented.

In a December 2015 statement to Us Weekly, Dahl confirmed that the couple was kaput. People reports it was amicable and largely due to their busy careers. According to The Daily Telegraph, however, Rose hinted that cheating may have been a factor, but later deleted the Instagram post.

Following her Orange Is the New Black role, Ruby Rose's newfound fame in the United States helped her up her dating game, and she started being linked to higher profile American celebs. This included a rumored romp with Demi Lovato, though Rose planted the seed a couple years before she broke out stateside. According to Metro, in 2013, the actress claimed to have jumped into bed with the singer, who was publicly dating Wilmer Valderrama. The whole thing snowballed to the point that The Atlantic started wondering if Lovato's hit "Cool for the Summer" was actually about the Batwoman star.

According to a source who spoke to Life & Style, Rose and Lovato allegedly "dated for two years" while the singer was on "a break" from Valderrama, but Lovato refuted the whole thing when Complex asked her point blank if "Cool for the Summer" was about the Australian model. No, it wasn't. No, they didn't have a relationship, but when the magazine asked if the pair had hooked up, Lovato curiously danced around the question.

Though these two may have not officially dated, they reportedly do share one thing in common: Lauren "Kittens" Abedini. According to Seventeen, in 2017, Lovato was spotted holding hands with the DJ, who was also rumored to have dated Rose. "Demi Lovato dating Lauren Abedini who used to date Ruby Rose who had a thing with Demi is actual gay culture," wrote one Twitter user.

Ruby Rose and Halsey have two very fervent fan bases, who certainly ran with the idea of Ralsey. The pair didn't help themselves with that rumor, either. In 2018, years after they were allegedly spotted on their first date, Halsey wrote a poem for the actress, telling Hit Network that "Ruby's like poetry already."

According to E! News, the whole thing began shortly after Rose's split from Phoebe Dahl in 2015. In December of that year, the actress was spotted out on a "fun day date" with the Badlands singer, who could've been supporting her gal pal through a breakup just as easily as she could've been Rose's new suitor. Based on a Billboard interview, Halsey had split from Norwegian producer Lido some months prior and had yet to be seen in the arms of Jared Leto at Coachella. E! News couldn't determine the nature of the date, but did point out that the romance rumors had been floating around for a while. 

Like we'd expect, the pap photos pretty much set the Internet on fire. One Elite Daily writer even begged in all caps, "COULD THEY, DESPITE JUST GOING ON THEIR FIRST DATE LIKE A DAY AGO, BECOME THE COUPLE OF THE YEAR?" That same writer claimed the paparazzi snaps were "basically engagement photos." Sadly, Halsey never became Rose's fifth engagement. At the time of this writing, it looks like the pair are just friends.

Summer loving had Ruby Rose a blast, until it almost turned deadly. In 2016, the star reportedly had a short-lived summer fling with model-entrepreneur Harley Gusman, which ended in some pretty serious alleged drama. According to E! News, the romance rumors started in June of that year with a date to the Hollywood restaurant Katsuya, and the couple fanned the flame with a visit to Rhode Island for Taylor Swift's now iconic Fourth of July party (you know, the one where Tom Hiddleston was ripped apart in the tabloids for wearing an "I [heart] T.S." tee). Unfortunately, by August, it had fizzled out.

A source that spoke to E! News claimed Rose was focusing on her career and planned to spend the rest of the year filming outside of the country, but the Daily Mail thought the breakup had more to do with Rose's bestie, Courtney Africa McLellan. In a since-deleted Instagram post, the star revealed she "broke up with a girl purely because she endangered" her friend's life by "being reckless on a jet ski." Flash back to Rose's holiday in Ibiza, which happened the same month she split from Gusman. Paps caught a bikini-clad Rose appearing to sternly talk to Gusman and McLellan, who were both sat on a Jet Ski. Gusman was driving, and McLellan was on the back. Rose wasn't playing.

Ruby Rose had dated The Veronicas' Jess Origliasso all the way back in late-aughts, but the pair rekindled their romance at the end of 2016. It all happened over a steamy music video shoot where Rose played director. In an interview with Cosmopolitan, Rose revealed that she walked onto the set of The Veronicas' "On Your Side" video a single woman and walked out with a girlfriend.

"It happened as we were shooting it. I've known her for 10 years. We dated in 2009 and we've been best friends for a long time," she told the glossy, adding, "It was the last thing I expected to happen, but when you're involved in something you're both passionate about it's not unusual to become attracted."

Origliasso told Cosmopolitan that their reunion was "the craziest thing," but the relationship seemed a bit unremarkable. In an interview with J-14, Rose revealed the couple played music every night, sang, and cooked dinner. The former two activities likely helped Rose prepare for her role in Pitch Perfect 3, but the whole relationship was apparently doomed from the very first note.

Ruby Rose's relationship with Jess Origliasso was sweet while it lasted, and bitter thereafter. According to InStyle, the pair called it quits a few months before Rose announced it publicly in April 2018. At first, it seemed amicable, but it was a slow burn. Seven months or so after going public with their breakup, Origliasso accused the actress of harassment.

The lid blew off the former couple's clearly far-from-acrimonious split when Origliasso shared an Instagram photo of her new flame, Kai Carlton, with the caption, "luckiest." In comments captured by InStyle, Rose made the seemingly innocuous remark, "Congratulations, so happy for you both." That's when Origliasso fired back, "I have requested you not contact me for over four months now ... the fact you continue to ignore this to contact me here publicly under the guise of wishing me well, is continued harassment."

A year later, Origliasso publicly addressed the painful breakup in an episode of MTV's The Veronicas: Blood Is for Life, where she claimed it nearly destroyed her relationship with her twin sister. "Lis and I didn't talk for a year. I was in a relationship that wasn't good for me. I became isolated," she tearfully said (via the Daily Mail). "I had nobody anymore, I only had my relationship."

Origliasso and Carlton got engaged in October 2019, and at the time of this writing, Rose appears to be single.