20 Most Iconic Celebrity Valentine’s Day Moments
From grand romantic gestures to surprise proposals, these iconic celebrity Valentine’s Day moments prove that love in Hollywood can be as extravagant as it is heartwarming.
- Chris Graciano
- 6 min read
Celebrities have the ideal opportunity to express their love in extravagant and memorable ways on Valentine’s Day. They have elevated romance to a new level, from Beyoncé’s island retreat to Kanye West’s rose-filled suite for Kim Kardashian. This listicle contains 20 of Hollywood’s most memorable and breathtaking Valentine’s Day moments.
1. Kanye West’s Floral Wonderland for Kim Kardashian (2019)
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Kanye West went all out by filling an entire room with single-stem roses in vases while Kenny G played a private saxophone serenade. The mesmerizing sight, combined with live music, left Kim speechless. Few gifts scream “romance” like a personal concert from a legendary musician.
2. Beyoncé and Jay-Z’s Private Island Escape (2013)
Jennette F. Everett on Wikimedia Commons
For Valentine’s Day, Jay-Z surprised Beyoncé with a lavish trip to a private island in the Bahamas. The ultra-exclusive getaway included candlelit dinners, breathtaking views, and total seclusion.
3. Travis Barker’s Rose-Filled Beach Proposal to Kourtney Kardashian (2022)
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Although technically a proposal, this over-the-top moment happened just a day before Valentine’s Day. The Blink-182 drummer set up a massive heart-shaped arrangement of roses on a California beach. The romantic display, set against the sunset, became one of the most talked-about engagements of the year.
4. Justin Bieber’s Serenade for Selena Gomez (2011)
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Back when Jelena was the hottest couple in young Hollywood, Justin Bieber pulled off a grand romantic move. He rented out the entire Staples Center for a private screening of Titanic just for Selena. It was the ultimate teen heartthrob gesture, proving his love in cinematic style.
5. David Beckham’s Jewelry Surprise for Victoria Beckham (2006)
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Known for his lavish gifts, David Beckham gifted Victoria an $8 million diamond necklace for Valentine’s Day. The dazzling piece was part of a private dinner celebration at an exclusive restaurant. When it comes to grand gestures, Beckham never disappoints.
6. Joe Jonas and Sophie Turner’s Parisian Getaway (2019)
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Joe Jonas whisked Sophie Turner away to Paris for a romantic Valentine’s weekend. The couple explored the city of love, indulging in gourmet food and cozy strolls along the Seine.
7. Kim Kardashian’s $73,000 Bracelet from Kris Humphries (2011)
The Heart Truth on Wikimedia Commons
Before their short-lived marriage, Kris Humphries gifted Kim a Lorraine Schwartz diamond bracelet worth $73,000. The extravagant piece was a testament to how Hollywood couples go all out for love. Sadly, the sparkle didn’t last long, as the couple split later that year.
8. Chrissy Teigen and John Legend’s Cozy Homemade Celebration (2020)
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Rather than opting for an extravagant outing, Chrissy Teigen and John Legend chose to stay in. They cooked a romantic meal together, shared heartfelt messages, and enjoyed time with their kids.
9. Katy Perry’s Helicopter Date with Orlando Bloom (2019)
Ali Shaker/VOA on Wikimedia Commons
Orlando Bloom took Katy Perry on a breathtaking helicopter ride before proposing with a stunning flower-shaped diamond ring. The magical aerial view set the stage for an unforgettable moment.
10. Offset’s Apology-Filled Valentine’s Day for Cardi B (2019)
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In an attempt to win back Cardi B after their brief split, Offset went all out with a lavish floral arrangement. He covered their home in thousands of roses and gifted her extravagant jewelry. The grand gesture worked, and the two eventually reconciled.
11. Prince Harry and Meghan Markle’s Quiet Canadian Retreat (2017)
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Before their royal engagement, Harry and Meghan spent a cozy Valentine’s Day in a secluded cabin in Canada. Away from the public eye, they enjoyed home-cooked meals and uninterrupted quality time.
12. Rihanna’s Surprise Getaway from Hassan Jameel (2018)
Ilikeriri on Wikimedia Commons
When she was dating billionaire Hassan Jameel, Rihanna received a lavish surprise trip to an undisclosed tropical location. The exclusive getaway featured luxury accommodations and complete privacy. Even for a global superstar like Rihanna, the moment was unforgettable.
13. Ashton Kutcher and Mila Kunis’ Low-Key Date (2016)
Lance Cpl. Johnny Merkley on Wikimedia Commons
Instead of indulging in Hollywood’s over-the-top traditions, Ashton Kutcher and Mila Kunis kept things casual. They grabbed burgers from their favorite fast-food joint and spent the night watching movies at home.
14. Jennifer Lopez’s Diamond Bracelet from Alex Rodriguez (2018)
D. Benjamin Miller on Wikimedia commons
A-Rod showered J.Lo with diamonds, gifting her a stunning bracelet on Valentine’s Day. The romantic moment was captured in a heartfelt Instagram post, melting fans’ hearts. Though their relationship didn’t last, the memory of this luxurious gift remains.
15. George and Amal Clooney’s Candlelit Venice Dinner (2017)
White House/Pete Souza on Wikimedia Commons
For a truly classic Valentine’s date, George Clooney took Amal to a private dinner in Venice. With gondolas passing by and soft candlelight setting the mood, it was straight out of a romance film. When it comes to love, Clooney knows how to set the bar high.
16. Tom Cruise’s Eiffel Tower Proposal to Katie Holmes (2005)
Mass Communication Specialist 2nd Class Keenan Daniels on Wikimedia Commons
Few locations are as romantic as Paris, and Tom Cruise took full advantage of that. He proposed to Katie Holmes at the top of the Eiffel Tower on Valentine’s Day.
17. Blake Lively and Ryan Reynolds’ Humorous Valentine’s Day (2021)
Sgt. Michael Connors on Wikimedia Commons
Known for their playful relationship, Ryan Reynolds and Blake Lively celebrated Valentine’s Day with humor. Ryan shared an unflattering but adorable candid photo of Blake, proving love doesn’t always have to be serious. Laughter, after all, is one of the strongest love languages.
18. Heidi Klum’s Skywriting Surprise (2009)
The Heart Truth on Wikimedia Commons
Seal, Heidi Klum’s then-husband, surprised her with a love note written in the sky. The grand gesture left her speechless as she watched the words form above their home. Few gifts are as poetic and timeless as a declaration of love in the clouds.
19. Nick Jonas’ Romantic Getaway with Priyanka Chopra (2019)
Musicianoftheuniverse on Wikimedia Commons
Nick Jonas planned an intimate vacation for Priyanka Chopra, complete with luxurious accommodations and stunning views. The couple shared glimpses of their romantic escape on social media, delighting fans. Their love story continues to be one of Hollywood’s sweetest.
20. Angelina Jolie and Brad Pitt’s Family-Focused Valentine’s (2015)
Airman 1st Class Tanaya M. Harms on Wikimedia Commons
Rather than an intimate date, Brad and Angelina celebrated Valentine’s Day with their children. They enjoyed a day filled with family activities and handmade gifts. Love, for them, wasn’t just about romance—it was about cherishing family.