Looking Back on Orlando Bloom's Surprising Dating History

From Kate Bosworth to Katy Perry, here's the Lord of the Rings star's romantic journey over the years

By Tierney Bricker Feb 17, 2019 11:00 AMTags
Watch: Katy Perry's Engagement Ring: Get All the Details

"I'm completely in love with the idea of love."

And nothing quite shows off a love for love than proposing on Valentine's Day with a $5 million dollar engagement ring featuring a pink center stone.

Orlando Bloom admitted to his in an interview with Elle in 2013, going on to say, "Love is what we aspire to most in our lives." 

And ever since he first made his debut in Hollywood after playing Legolas in the first Lord of the Rings movie, Bloom, 42, has made headlines in his journey leading up to proposing to Katy Perry on Feb. 14. 

Looking Back At Orlando Bloom's Dating History

The ring features an oval-shaped diamond surrounded by eight diamonds to "assemble a flower 'in bloom' - this ring is truly one-of-a-kind and wildly valuable," Andrew Brown, President, WP Diamonds told us of the design of the stunning rock, which Perry, 34, proudly displayed on Instagram. ""full bloom," Perry captioned the selfie with her fiancé.

And their relationship has spent quite some time blooming, with a look back over the actor's dating history over the years provides some great gossip nostalgia, including an alleged love square involving Justin Bieber and Selena Gomez, and a possible hook-up with Lindsay Lohan.

First Public Relationship

Fresh off the major success of the first Lord of the Rings film, Bloom made headlines when he began dating Kate Bosworth, fresh off of her breakout role in Blue Crush, and though they were two stars on the rise, they managed to keep their romance pretty private.

"I keep everything that's private private," Bosworth told People during their relationship.

Bloom also tried to maintain his privacy, but did reportedly gush about his girlfriend, sort of, to a British newspaper in 2004. "I'm in love with love," he said. "It's heavenly when you're falling for someone and can't stop thinking about her."

Scheduling Issues

After two years together as one of young Hollywood's hottest couples, Bloom and Bosworth announced their split in a joint statement from their rep.

"They did decide to take some time apart due to their upcoming work schedule, and they remain very close," the statement read. "It was a mutual decision."

Years later, Bosworth opened up about the split in a 2011 interview with Sunday Times Style.

"You know when you put all your chips into something, then it disappears? The [split] sent me into such pain, I think I had actual vertigo. I was like, ‘Is this my new reality? Will anything be normal again?' "she said. "Then one day you wake up and you think, 'OK, I'll never be the same, but I'll survive and I'll grow from it.'"

10 years after their split, the former couple had a friendly reunion at the 2015 Dior Homme Cocktail Reception.

In 2013, Bosworth would marry Michael Polish, her director beau she met and fell for while filming Big Sur in 2011.

Lohan's List

Back in 2014, Hollywood was rocked when In Touch Weekly released photographs of a list naming 36 Hollywood hunks that Lohan allegedly had sex with, with Lohan later revealing it was legit, explaining what had happened during an appearance on Watch What Happens Live.

 "You know, I'm going to get serious for a second," the actress told Andy Cohen. "That was actually my fifth step in AA at Betty Ford. And someone, when I was moving during the OWN show, must have taken a photo of it. And so that's a really personal thing and it's really unfortunate."

Some of the names included? Ashton KutcherRyan PhillippeEvan PetersJamie DornanZac EfronJustin TimberlakeColin FarrellHeath LedgerJames FrancoAdam LevineGarrett Hedlund, and Orlando Bloom (though she wrote "Orli Bloom").

No details have ever emerged (nor confirmation BTW) but this felt like an important and necessary blast from the past. 

A Brief Moment With Penelope Cruz

After they were spotted on two separate occasions at clubs together, including his 30th birthday celebration in 2007.

At the time, an eyewitness dished to E! News that the two were canoodling at his party at the Hollywood Roosevelt Hotel. 

"He couldn't keep his hands off of her," the source said. "He would just keep grabbing her and kissing her. It was very sweet." 

Alas, they are also quick to add: "He was wasted. He would just grab her face and give her a big kiss on the cheek." 

The beginning of an epic romance it was not, and the two never seemed to confirm or deny if they were romantically linked. 

Love At First Sight

While they began dating in 2007 after meeting through a mutual friend, the actor and Victoria's Secret model made their public debut as a couple at the Sydney's Doncaster Day at Randwick Racecourse in 2008.

And it seemed like it was love at first sight and more for Bloom when he first met his future wife, coyly telling Elle in 2013, "It was a lot of things. And actually, I'd rather not talk about it."

It also seemed like it was quite serious from the start, with Kerr admitting to People in 2008, "No one knows what will happen in the future. We're happy together and that's it."

In July 2010, just one month after their engagement made headlines, the couple quietly wed in an intimate ceremony, with the news only getting out because Kerr revealed her honeymoon would cause her to miss a work commitment in her native Australia. 

"[Australian department store] David Jones very graciously released me during this period so we could celebrate an intimate ceremony and honeymoon together," Kerr said in a statement. "I am enormously grateful to David Jones to have been given this time to enjoy such a special moment in my life."

In Like Flynn

After revealing in August 2010 that she was pregnant with the couple's first child, Kerr and Bloom welcomed their son, Flynn, in January 2011.

Her hometown of Gunnedah in Australia was "really excited" about his arrival, with Mayor Adam Marshall gushing, "She still has strong family links here and we are very proud of her. We would like to see Miranda, Orlando and the new bub in Gunnedah."

In 2013, Bloom opened up about balancing work and fatherhood in an interview with InStyle, saying, "I won't spend more than two or three weeks away from him," while adding Kerr doesn't spend more than a week away from their son.

"She flies somewhere for work, I take care of Flynn. I go off to work, she takes care of Flynn," he explained. "Or, you know, we're together, and we just make it work. We're not conventional in any way, shape or form."

The couple would be photographed for the last time before announcing they had been "amicable separated" for months on Oct. 24, enjoying a nighttime stroll in New York City with Flynn.

Split With Miranda Kerr

After three years of marriage and some rumors of their relationship being on the rocks, Bloom and Kerr officially announced their split.

"They have been amicably separated for the past few months," read a joint statement from the couple exclusively given to E! News in 2013. "After six years together, they have recently decided to formalize their separation. Despite this being the end of their marriage, they love, support and respect each other as both parents of their son and as family."

When it came to their divorce, their son Flynn was the top priority.

"Flynn was 2, so it was really hard to make the decision, but our son is our priority so you have to come from love," Kerr told The Edit in 2016. "You have to be kind."

And the former couple has made co-parenting look pretty easy since their split, with Kerr eventually marrying Snapchat co-founder and billionaire Evan Spiegel in 2017.

"[Orlando and I decided] that we had to know the person for six months and feel good about them," Kerr revealed to The Edit. "Evan met Flynn, so yeah, things are going well. Orlando thinks he's great. We're just a modern family now!"

In 2017, Bloom posted a sweet Mother's Day tribute to his ex, captioning a photo of Flynn hugging an ad campaign featuring his mom with, "we came across this billboard in china while he was visiting me on set he loves his mum and what's not to love- she's a wonderful mother a great friend and co parent so blessed and grateful."

Selena Gomez

Oh boy, talk about gossip nostalgia. Bloom and the "Come and Get It" singer met in March 2014 at We Day California, with romance rumors immediately popping up given Bloom's recent separation and Gomez's on-and-off relationship with Justin Bieber.

A source at the time told E! News "they are not dating," even when they were spotted out to dinner together a month later, memorably sitting on a curb...quickly moving away from each other once the paparazzi appeared. 

But here's where the story gets interesting: back in 2012, rumors circulated that Bieber and Kerr had gotten friendly when he was the performer at that year's Victoria's Secret fashion show. At the time, Kerr was still married to Bloom, and her lawyers released a letter saying that any implications of their client hooking up with the bad boy singer were "false and defamatory."

And now here's where this love square gets notorious: In July 2014, Bloom and Bieber got into a physical altercation at a restaurant in Ibiza.

As the legend goes, Bieber allegedly made a crude comment about Kerr, with the Pirates of the Caribbean actor reportedly taking the first swing at Bieber. (After the fight, Bieber took to Instagram to post and quickly delete a modeling photo of Kerr in a bikini with the crown emoji as his caption.)

But since that eventful night, the drama seemed to have calmed down, with Bloom, Gomez and Kerr all attending the Vanity Fair Oscars party the following year, and Gomez wished him a happy birthday in 2016, revealing her cute nickname for him: Orly.

Sparks Fly

It's not often we get to see the exact moment a pair of celebrities hit it off, but that's exactly what happened for Bloom and Katy Perry, whose first meeting (and flirtation) at Netflix's Golden Globes party in January 2016 was photographed for all to see. It was no surprise when it was reported the two were an official item months later. 

The American Idol judge made it Instagram official with her new love in May 2016 and after those infamous photos of a naked Bloom paddleboarding nearly broke the Internet while the couple was vacationing in Italy nearly broke the Internet, an engagement seemed imminent, according to an insider.

"They are in love and happier than ever. [Orlando] would like to get engaged to [Katy] before the year is up," a source close to the couple told E! News in the summer of 2016. 

The Surprise Split

After 10 months of dating, the couple released a joint statement announcing their breakup. 

"Before rumors or falsifications get out of hand we can confirm that Orlando and Katy are taking respectful, loving space at this time," their reps said. 

At the time, a source told us that it was the "Roar" singer's decision to end it. "It was a few events that happened over the past few months. They both still love each other very much, though, and getting back together could happen once they have some space." The insider added they would still be in contact as Perry had formed a bond with Flynn. 

"They did discuss a future together during their relationship. They had an enormous amount of love for one another."

Clearly, the door was still open, something Perry seemed to hint at  when she tweeted, "How bout a new way of thinking for 2017. U can still b friends & love ur former partners! No one's a victim or a villain, get a life y'all!"

The Reconcilation

After some time apart, the couple was spotted together at an Ed Sheeran concert in August 2017, with a source at the time telling us, "They have never cut communication since they broke up."

Our insider made it clear that Bloom and the "Teenage Dream" songstress were focusing on "mending their relationship. They've had some really good talks and have a better understanding on their needs. Time will tell at this point, but [things are] looking very positive."

Their reconciliation was all but confirmed when the couple was spotted vacationing together in the Maldives in January 2018, and by April, Perry confirmed she was no longer single during an interview with Entertainment Tonight

The Proposal

On Valentine's Day, Bloom popped the question to Perry shortly after their three-year anniversary, and he did it in style.

"Full bloom," she wrote on Friday alongside a snapshot of the couple. The picture also gave fans a close-up of Perry's ring—which appeared to have a colorful center stone, as well as several surrounding diamonds. The cost? 

"Katy's unbelievable engagement ring from Orlando Bloom would retail in the range of $5 million," Andrew Brown, President, WP Diamonds told E! News. "What looks to be a 4-carat fancy vivid pink oval shaped diamond arranged with eight white diamonds around it to assemble a flower 'in bloom' - this ring is truly one-of-a-kind and wildly valuable."

No wonder Bloom captioned his Instagram photo announcing the happy news with "Lifetimes." 

Want more? Check out Bloom and Perry's long road to engagement

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