Orlando Bloom is single and ready to mingle (with Sydney Sweeney, potentially), which means the time has come to take a stroll through his dating history. This man has been famous since the early aughts, but please be advised that his relationship with Katy Perry—while his longest—isn't his only A-list love story. Here's everyone Orly has dated, both definitely and allegedly.

Kate Bosworth: 2002 to 2005

"superman returns" world premiere sponsored by belstaff
John Sciulli//Getty Images

These two were in a super low key relationship for several years before eventually parting ways. Though, not so low key that their rep didn't issue a formal statement during their breakup! As they put it to People, "They did decide to take some time apart due to their upcoming work schedule, and they remain very close. It was a mutual decision."

premiere of warner bros. "superman returns" afterparty
Kevin Winter//Getty Images

Kate spoke about the relationship to Vogue (via the Daily Mail), saying "Orlando and I met when we were kids. Blue Crush hadn't come out. Lord of the Rings hadn't come out. He was the first big heartbreak. First love—you feel like it's the be-all and end-all. To put as little pressure on the relationship you're in is very important. I regret that it was too intense for both of us."

Penélope Cruz: 2007

This was just a rumored hookup, but E! News did speak to a source who said they were spotted getting cozy at Orlando's 30th birthday party. Per an eye witness "He couldn't keep his hands off of her. He would just keep grabbing her and kissing her. It was very sweet."

Anyway, here's a pic of Orlando and Penélope in 2007 (with Leonardo DiCaprio, randomly).

global green usa 3rd annual pre oscar celebration to benefit global warming inside
Michael Caulfield//Getty Images

Miranda Kerr: 2007 to 2013

audi clean diesel dinner inside
Alexandra Wyman//Getty Images

Orlando and Miranda met in late 2007 and got engaged in June 2010. They married just one month later in July, and in August Miranda revealed that she was pregnant. The couple welcomed their son Flynn in January 2011 and parted ways two years later—in Fall 2013. Orlando's rep issued a statement at the time, saying "Despite this being the end of their marriage, they love, support and respect each other as both parents of their son and as family."

"shakespeare's romeo and juliet" broadway opening night after party
Bruce Glikas//Getty Images

For what it's worth, they seem to get along great as co-parents!

Katy Perry: 2016 to 2017

Katy and Orlando got flirty at the 2016 Golden Globes party and started dating shortly after. Proof:

the weinstein company and netflix golden globe party, presented with deleon tequila, laura mercier, lindt chocolate, marie claire and hearts on fire inside
Kevin Mazur//Getty Images

But alas, they split a year later in February 2017 and their reps issued a joint statement to People, saying "Before rumors or falsifications get out of hand, we can confirm that Orlando and Katy are taking respectful, loving space at this time."

For what it's worth, Katy made it clear that things were amicable:

Selena Gomez (Rumor!): May 2016

Gonna rewind real fast. Before Katy and Orlando split in 2017, multiple outlets reported that Selena and Orlando had hooked up to make Miranda Kerr and Justin Bieber jealous after they were spotted flirting at the Victoria’s Secret Fashion Show. But Katy called the reports "conspiracy theories" and posted this:

Which Sel retweeted:

Nina Dobrev: April 2017

There were brief reports that Orlando was dating Vampire Diaries star Nina Dobrev in 2017, though a People source said "It’s super casual." So casual, in fact, that things fully fizzled out and everyone forgot about it.

Here's a blurry pic of them out and about with friends that month, though!

celebrity sightings in los angeles april 12, 2017
Hollywood To You/Star Max//Getty Images

Katy Perry: 2018 to 2025

Katy and Orly got back together in early 2018, and by March a source told People that "They are dating but not necessarily putting a label on it. They are not girlfriend and boyfriend. They do seem very happy together though."

The pair ended up getting engaged on Valentine's Day 2019...

...and then Katy announced that she was pregnant in March 2020. She and Orlando went on to welcome their daughter Daisy Dove!

Things kept trucking along until 2025, when Orlando and Katy hit a rough patch. Their last public appearance together was at the Vanity Fair Oscar Party in March:

2025 vanity fair oscar party hosted by radhika jones arrivals
Taylor Hill//Getty Images

After weeks of speculation, Us Weekly finally confirmed their split in June, speaking to a source who said "Katy and Orlando have split but are amicable. It’s not contentious at the moment. Katy is of course upset but is relieved to not have to go through another divorce, as that was the worst time in her life."

The insider added that the breakup was "a long time coming" since things "have been tense for months," and they've been "living apart since Katy has been on tour."

That brings us up to date, but stay tuned...