Katy Perry and Orlando Bloom, who share a daughter and have been engaged for four years, recently had a memorable moment when the actor presented his fiancée with the MTV Video Vanguard Award at the 2024 MTV Video Music Awards. Take a look back at their relationship timeline and more!

Orlando Bloom and Katy Perry‘s whirlwind romance is something that’s straight out of a fairytale! Though the singer, 39, and actor, 46, have had their fair share of ups and downs (and what Hollywood couple hasn’t?) it’s the good times we’re sure they’ll remember.

The couple welcomed their first child together, a beautiful daughter named Daisy Dove Bloom, with an announcement shared by Katy on her Instagram in August of 2020. But that’s not the end of their story — their wedding is still on hold — and it’s certainly not the start. Relive every moment of Katy and Orlando’s romance, from their first meeting, to their romantic engagement and beyond!

Katy and Orlando First Meet at the 2016 Golden Globes

Katy and Orlando first laid eyes on one another (romantically) at the Golden Globes in January of 2016. They were spotted flirting and chatting closely together throughout the night, which instantly sparked romance rumors between the pair. The “Daisies” singer donned a sultry pink dress, while the Lord of the Rings alum looked dapper in a black and white tuxedo.

Katy Makes Her Relationship With Orlando Instagram Official

Just a few months after Katy and Orlando’s Golden Globes PDA, the singer shared this photo of the pair posing on a large staircase in Cannes in May of 2016. They wore white robes in the photo, which marked Katy’s first social media post with the actor.

Katy and Orlando Split

Katy and Orlando split in early 2017 after nearly one year of dating. The singer addressed the breakup after multiple reports alleged that the pair had a nasty split. “HOW BOUT A NEW WAY OF THINKING FOR 2017,” she wrote on Twitter in March or 2017. “U can still b friends & love ur former partners! No one’s a victim or a villain, get a life y’all!” she concluded.

Katy and Orlando Reconcile and Make Their Red Carpet Debut

It’s unclear exactly when and how the couple reconciled in 2018. However, Katy shared numerous social media posts in April, which indicated that they were back on. She even tagged Orlando in a photo on Instagram that showed Katy on a private jet while holding a drawing of the actor. Katy and Orlando then made their red-carpet debut as a couple when they attended the Gala for the Global Ocean in Monte Carlo, Monaco in September of 2018.

Katy and Orlando Celebrate Her 34th Birthday After Reconciling

Just one month after their red carpet debut as a couple, Katy celebrated her 34th birthday with Orlando. The pair enjoyed a romantic dinner at Barton G. restaurant in West Hollywood on October 25, 2018 (the day of her actual birthday). The private dinner began around 6:15 P.M and the couple exited the restaurant (seen above) at 8:45 P.M. Katy rocked a hot pink, skin tight, latex dress, while Orlando was dressed casually in grey pants and an army green jacket.

Orlando Proposes on Valentine’s Day in 2019

Orlando popped the question to Katy with a $5 million flower diamond ring with a ruby red center on February 14, 2019. She shared a closeup photo of her ring to Instagram, as the couple’s faces were partially pictured in the post. Orlando pulled out all the stops for the big occasion, having decorated the room he proposed in with tons of red heart-shaped balloons.

At the time, multiple jewelry experts weighed in on the unique diamond ring in exclusive interviews with HollywoodLife. “I would insure this ring for at least half a million dollars if it’s truly a ruby,” Ritani’s VP and 20-year diamond expert, Josh Marion, explained. “If it’s a vivid pink diamond, it would be worth around $5 million.”

Gemologist and diamond expert, Grant Mobley, said, “The white diamonds in the halo appear to be .30 carats each, making the diamond halo 2.5 carats total. This is a classic floral halo design in yellow gold, with milgrain etching around the diamond settings. The center stone [appears to be] an oval-shaped ruby with beautiful red color around 2 carats,” Mobley explained, adding, “Natural gemstones can be difficult to value accurately without seeing them in person.”

Additionally, experts at JamesAllen.com added, “The ring looks to be a 4 carat vivid pink diamond set in a yellow gold band with a halo of round diamonds. The approximate cost at a traditional retailer is $6 million.”

Katy Supports Orlando at the Premiere of His ‘Carnival Row’ Show

Katy was by Orlando’s side at the red carpet premiere of his Amazon show, Carnival Row in Los Angeles, CA on August 21, 2019. The engaged couple was all smiles on the red carpet together.

Katy Opens Up About Her Relationship With Orlando’s Son

The actor has a nine-year-old son, Flynn Bloom, with ex-wife Miranda Kerr. In September of 2019, Katy told Ellen DeGeneres that being around Flynn has “matured” her. “We have to be out the door at 7:30 to be there at 8:15 and we cannot be late,” she said, seemingly referencing car pickups with Miranda, who she has a friendly relationship with. “I used to not wake up until 11 a.m. and now I’m in bed like a normal person at 10 p.m., just, like, falling asleep. … I guess this is adulting,” Katy explained, adding, “That’s why I still dress like a child, to fight against!”

Katy and Orlando Postpone Their Wedding

Orlando revealed in March (2020) that they were thinking about putting their dream nuptials on hold due to the COVID-19 pandemic. The couple’s wedding was initially supposed to take place in Japan at the end of 2019. Katy later clarified that she would not be marrying Orlando in 2020, due to the difficulties of planning a wedding during the global health crisis.

“You can’t plan anymore in 2020 because those plans are ­always canceled… Everyone has to take life one week at a time right now,” she told The Mirror in an interview published on July 25, 2020. Nonetheless, Katy noted that they’d eventually tie the knot. “Obviously, that will happen in the future, but for now we just want to deliver a healthy child,” the singer, who was pregnant at the time, explained.

“Katy and Orlando decided it was best to postpone their wedding for the time being,” a source close to the couple told HollywoodLife on July 26, 2020. “They are planning something really special and the timing didn’t work out at this moment in terms of the venue. They really want to make their wedding day incredible and they don’t want to rush the planning and possibly miss out on the little details.”

Katy Announces Her First Pregnancy in Her ‘Never Worn White’ Music Video

Katy first revealed her pregnancy in the music video for her song “Never Wore White,” which released on March 4, 2020. At the end of the video, Katy touches her then growing baby bump while wearing a white dress. She later confirmed the exciting news during an Instagram Live video.

Katy Reveals Mental Health Issues After Her 2017 Split With Orlando

Following her pregnancy announcement, Katy opened up about a low point in her professional and personal life, which led to her considering suicide in 2017. In a candid June 2020 interview, the then pregnant singer explained how she recovered from being “broken” after a breakup with Orlando and poor album sales in 2017.

“I lost my smile,” Katy told host Tom Power, while appearing on SiriusXM Canadian radio show “Q on CBC.” She went on to admit that she was left “wallowing” in her “own sadness” at the time. “I don’t know if my smile was ever fully, like, authentically mine but I was riding on the high of a smile for a long time. Which was the validation, love, and admiration from the outside world, and then that shifted,” Katy  recalled.

At the time (in 2017), “I had broken up with my boyfriend, who is now my baby-daddy-to-be, and then I was excited about flying high off the next record and the record didn’t get me high any more … The validation didn’t get me high, and so I just crashed,” Katy remembered. Clearly, the couple reconciled, and the rest is history.

Katy and Orlando Welcome Their First Child Together

The couple confirmed the birth of their first child with a joint statement on social media on August 27, 2020. Katy and Orlando partnered with charity UNICEF — with whom they’re Goodwill Ambassadors — to make the big announcement. “We are floating with love and wonder from the safe and healthy arrival of our daughter,” Katy and Orlando said in the caption of the post, confirming they named their baby girl Daisy Dove Bloom. The black and white photo showed Katy and Orlando holding their baby girl’s tiny hand.

Katy Perry and Miranda Kerr Appear on the Red Carpet Together

In January of 2023, Katy and Orlando’s ex Miranda Kerr proved their perfect co-parenting relationship by posing together at the G’Day USA Arts Gala in Los Angeles. Katy and the former supermodel looked gorgeous and friendly while smiling for the cameras, with Katy rocking a gold two-piece number, and Miranda slaying a skintight white midi-dress.

Katy Reveals Sobriety Pact With Orlando

In March of 2023, the singer revealed she and Orlando had embarked on a supremely supportive endeavor– a sobriety pact. “I’ve been doing a pact with my partner, and I want to quit,” she joked at an event at the time, per PEOPLE. “I can’t cave. I made a promise. Three months.”

Several months later, in June of 2023, she again addressed the pact and what inspired them to do it. “We did this because he’s shooting a movie in London right now that’s taking every ounce of his focus, and so I wanted that opportunity to be supportive,” she told the outlet. “It’s really hard to do anything, whether that’s doing a cleanse or a reset, unless your partner’s doing it. So, doing it together makes it so much easier.”

Katy and Orlando At the 2024 MTV Video Music Awards

The couple attended the 2024 MTV Video Music Awards in Elmont, New York, where Katy, born Katheryn Hudson, was honored with the Video Vanguard Award. She joins a list of past recipients, including Shakira in 2023 and Nicki Minaj in 2022. Orlando presented her with the award and told the audience, “You know her as a global superstar… I know her as a mother, as a partner who brings that same love and joy to our family. You fell in love with her as Katy Perry. I fell in love with her as Katheryn Hudson.”

After performing a medley of her greatest hits, including “California Gurls,” “E.T.,” “Lifetimes,” and more, she greeted the English actor with a kiss before expressing her gratitude in her speech for her partner, their daughter Daisy Dove, and her KatyCats. “My KatyCats, you have stood by me for a lifetime, and to the LGBTQ community, whom I recognize I would not be here without — you have shown me that you can be both kind and fierce. Thank you to Orlando for keeping me grounded, celebrating me, and doing the dishes. And lastly, for my Daisy, the only flower I’ll ever need,” she said.