Long before Ruby Rose rose to fame in America on 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 and has an entire
showbiz dating history we don't know much about. Let's take a look inside Ruby Rose's love life.
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.
"It doesn't make any sense to me, I wish I had the answer for why everywhere else seems to be
getting onboard that train, and why Australia is just so conservative in regards to it."
Since the legislation passed, Rose hasn't gotten down on one knee again. According to People,
her last engagement ended in 2015, 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."
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 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 when 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 this arrangement 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.
"Ugh. I said I wouldn't do that."
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, quote, "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 an adult shop with her ex, Lola Van Vorst, and tweeted about it. Rose
apparently urged the pair to remove their tweets, but Twitter is fast, and fans already saw them.
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, who beat the star for the top spot in 2003's Girlfriend Model Search.
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, quote,
"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 with their friends.
Days later, according to The Sunday Telegraph, Rose publicly announced the news on Facebook,
along with some photos of their loved-up holiday on the Gold Coast.
Rose and 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,
14 hours ahead of Melbourne. Rose didn't move stateside until 2013. A source told the outlet:
"It's sad they've broken up and both women are determined to
remain close but the relationship wasn't working."
McNeil was notably torn up about the broken engagement. In an interview with WHO magazine,
she admitted that she had to, quote, "take a step back" from modeling, saying:
"I had this growing sense of losing myself,
and I needed the time to breathe and find my own voice. 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, Rose called McNeil her, quote, "favorite person" in an Instagram birthday tribute.
"Love you." (kiss)
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.
At the time, The Daily Telegraph hailed them as, quote, "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 Autumn/Winter 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 barbecue, but only under the pretense that she was
going to meet someone's pet pig. Instead, she ended up meeting her fourth fiancée.
That someone was Phoebe Dahl, who was immediately struck by the model...
even though she was already in a relationship. Dahl told Out in 2015:
"[T]he second I saw Ruby, I completely fell for her. It sounds corny,
but it was love at first sight. Apparently, she felt the same thing."
According to People, Rose asked for Dahl's hand in marriage four times before the designer said yes.
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, 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 on Instagram that cheating may have been a factor, but later deleted the 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
ever-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.
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 shared a poem she wrote for the actress with Hit Network.
"Ruby's like poetry already, her name is poetry. Ruby Rose."
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, quote,
"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 speculated the duo might,
quote, "become the couple of the year," and claimed the paparazzi snaps were,
quote, "basically engagement photos." Sadly, Halsey never became Rose's fifth engagement.
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. Unfortunately, by August, it had fizzled out.
"Let's not turn this into a thing."
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, Rose revealed:
"I broke up with a girl purely because
she endangered Courtney's life being reckless on a jet ski."
Flash back to the star'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 on a Jet Ski.
Ruby Rose had dated The Veronicas' Jess Origliasso all the way back in the late-aughts,
but the pair rekindled their romance at the end of 2016. It 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 [...] 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, quote,
"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 the news
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 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 allegedly 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 very isolated. I had nobody anymore, I only had my relationship."
Origliasso and Carlton got engaged in October 2019, while Rose appears to be single.
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