The 9 Biggest Celebrity Engagements of 2025 So Far

The 9 Most Exciting Celebrity Engagements of 2025 (So Far)

Celebrity engagements never fail to captivate fans, and 2025 has already delivered an impressive lineup of surprise proposals and heartwarming announcements. From golden couples showing off dazzling rings on Instagram to beloved stars finding happiness a second time around, here are the most exciting celebrity engagements making headlines this year.

Zendaya and Tom Holland Spark Golden Globes Frenzy

When Zendaya stepped onto the Golden Globes red carpet this January debuting a gorgeous engagement ring, speculation spread instantly across social media. Fans had been rooting for the Spider-Man co-stars since their onscreen chemistry translated into real-life romance. While the couple has kept details private, Zendaya’s discreet but stunning ring was enough to set Instagram and Twitter abuzz with congratulatory messages and fan excitement. The understated announcement perfectly fit their deeply cherished, low-key style, setting a high bar for romantic news early in 2025.

Winnie Harlow and Kyle Kuzma Celebrate With a High-Flying Proposal

NBA star Kyle Kuzma chose a sky-high setting to propose to supermodel Winnie Harlow in February. While flying to Turks and Caicos for the All-Star Break, Kuzma popped the question mid-flight, turning their getaway into a once-in-a-lifetime celebration. The couple later took to Instagram to share a series of joyful photos featuring Harlow’s sparkling ring, the tropical backdrop, and plenty of happy tears. Their love story, which began in 2020 and went public a few months later, continues to inspire fans with its blend of glamor and genuine affection.

Jason Segel and Kayla Radomski Say ‘Forever Yes’

Beloved actor Jason Segel found his happy ending with actress and dancer Kayla Radomski. After two years of dating, Segel proposed in June, and Radomski’s joyful “FOREVER YES” post on Instagram quickly garnered thousands of likes and celebratory comments. The accompanying photos captured the candid and emotional moment, as seen in her heartfelt slideshow. Engagement news like this reminds fans why Segel is so cherished: he brings the same warmth and sincerity to his real-life relationships as he does to the screen.

Crystal Hefner Starts a New Chapter With James Ward

Crystal Hefner, known for her previous marriage to Playboy founder Hugh Hefner, announced her engagement to marine biologist James Ward this spring. The proposal, which occurred at her home in Hawaii, featured a breathtaking six-carat diamond ring. Speaking to Us Weekly, Hefner shared how this engagement feels uniquely genuine compared to her first, emphasizing the importance of a partnership built on true friendship and support. This heartfelt perspective resonated across news outlets and fans alike, highlighting how love stories can evolve and deepen the second time around.

"My first wedding was part of a chapter that felt performative… This time, with James, it’s completely different. We’re best friends… Our wedding will reflect that — simple, heartfelt, and full of love," Crystal Hefner told Us Weekly.

Tanner Buchanan and Lizze Broadway Share Their Surprise

Best known for his roles in “Cobra Kai” and “He’s All That,” Tanner Buchanan surprised fans by announcing his engagement to longtime girlfriend and fellow actor Lizze Broadway. The pair opted for a soft launch, quietly dropping photos on social media before confirming the news. The engagement capped off years of dating and professional collaboration, with many in the entertainment industry offering their congratulations.

Chloë Grace Moretz’s Subtle Social Reveal

Rather than the grand gestures typical of Hollywood, Chloë Grace Moretz chose a subtle approach to announce her engagement. Fans discovered the news through a cleverly concealed photo dump on Instagram, sparking a wave of excited speculation before Moretz confirmed the engagement. This understated reveal resonated with followers, demonstrating how public figures are increasingly choosing authenticity over spectacle in sharing major milestones.

Social Media Frenzy Over Celebrity Engagements

In 2025, Instagram continues to play a crucial role in celebrity life announcements, with stars like Radomski and Harlow sharing firsthand glimpses of their joy. These posts often gather widespread attention, quickly making rounds on platforms such as X (formerly Twitter), where hashtags and trending topics celebrate each new match. It’s a testament to how social media both personalizes and amplifies these significant moments for fans worldwide.

The Growing Trend of Genuine Love Stories

This year’s engagement announcements reflect a growing desire for authenticity and connection. Whether it’s Zendaya and Tom Holland’s private happiness, Crystal Hefner’s quest for a truly meaningful partnership, or Chloe Grace Moretz’s quietly joyful reveal, celebrity couples are prioritizing genuine emotion over staged spectacle.

As proposals and engagement stories continue to unfold, readers can follow live updates and full photo galleries at top entertainment outlets like Wonderwall and Cosmopolitan, where every new “Yes!” gets the spotlight it deserves.

For more details on the latest celebrity engagement news, visit Wonderwall’s up-to-date coverage or Cosmopolitan’s ongoing tracker of A-list couples. To relive the standout engagement posts, check out Winnie’s Instagram for her engagement journey and Jason Segel’s fiancée Kayla Radomski’s heartfelt proposal slideshow.

This year isn’t over yet, and the love stories of 2025 are still unfolding—follow along as these new power couples plan their next chapters.