Planning the perfect proposal is no small feat. It’s that important moment when you and your partner commit to spending a lifetime together. How you ask sets the stage for your engagement and becomes a tale you’ll recount for years. The weight of those few words is undeniable.
We want to share intimate, unforgettable proposal stories from our Real Weddings. These couples generously shared their most cherished moments with us. From meticulously planned events to spontaneous and deeply sentimental gestures, these real-life stories offer glimpses into how love is declared. Join us in celebrating the joy, creativity, and heartfelt narratives that weave together each unique proposal, forming a beautiful tapestry of love stories.
Leather Jacket is a New Diamond
Evan returned from a work trip to Los Angeles, only to find Joey dressed in a striking tuxedo amidst a sea of roses and candles. Evan wondered: “Are we having a party I didn’t know about?” Joey led Evan to the end of the hallway, where there was a big box that said “put me on” – inside, a Tom Ford leather jacket because Joey knew that Evan did not want a diamond ring (but like a diamond, a good leather jacket is forever).
Once Evan put the jacket on, Joey got down on one knee with an engagement band inscribed in his handwriting. And he said yes!
Photo: Marry & Me
On the Backdrop of Childhood Memories
Eric chose the enchanting Montauk Lighthouse, a place close to the bride’s heart since childhood, for his marriage proposal. Eric and Francesca shared a moment full of love and hope in this serene and beautiful spot where she spent many happy days. Traveling from far away to this beloved place, Eric’s proposal was not just a question but a sincere expression of their deep connection and shared memories.
Photo: Duke Images
Can't Wait to Marry You
Angus and Kate‘s love story took an unexpected turn during the challenges of the COVID era. Undeterred by the lockdown, Angus orchestrated a unique proposal, enlisting the help of a contact who could craft a custom ring according to his specifications, all arranged seamlessly over Facebook Messenger. The proposal itself, however, was anything but conventional, as Angus had come up with an excuse for a waterfront champagne outing, all while COVID tracksuits. With Kate’s parents eagerly awaiting news, Angus had to improvise and pop the question swiftly when Kate innocently decided to share a pre-proposal photo of the picturesque scene and champagne. Despite the unconventional setting and the surprise nearly being spoiled, a shocked but delighted Kate exclaimed ‘yes,’ marking the beginning of their new chapter.
Photo: Callan Robison
Meet You Under THE Tree
Heidi and Nick‘s love story takes center stage in the romantic city of San Francisco, where Nick crafted a proposal to remember at Bernal Heights Park. Under the same tree and swing that witnessed their laughter-filled dating days, Heidi surprised Nick by playing ‘Way Back Home’ by Korean artist Shaun – a song they both unknowingly shared an obsession with. Their connection goes beyond musical harmonies, with shared favorites like coconut water from a Las Vegas juice shop, the delectable ‘McConnell’s Chocolate Covered Strawberries,’ and even a matching mole on their faces. Having legally tied the knot in San Francisco on 8/17/20, a date chosen for its symbolic fusion of ’17’ meaning ‘together’ in Chinese and ‘8’ symbolizing infinity, Heidi and Nick’s love story continues as an everlasting journey ‘forever together.
Photo: Bottega 53
A Symbolic Date
Cortland and Jared‘s engagement unfolds against the picturesque backdrop of Pelican Hill in Newport Beach, a place close to Jared’s heart. Elevating the significance and symbolism, their joyous moment aligns with the anniversary of the historic gay marriage Supreme Court ruling in June 2021.
Photo: Heirlume Photography
When the Whole City is at Her Feet
Lucas and Sydney‘s love story reached new heights three years into their journey as they explored the enchanting city of New York just before Christmas. Lucas plunged to one knee atop the iconic Top of the Rock, asking Sydney to be his wife. Fast forward to their wedding day, where Lucas, in his heartfelt vows, revealed that from their very first date, he knew Sydney was his person, destined to share a lifetime of love together.
Photo: Sarah Boller
Let's Make a TikTok
Scott had a special plan to propose to Mark, but he needed to keep it a secret. Since they usually share everything, Scott told Mark they were going to the Bahamas for a belated birthday celebration. This way, Mark wouldn’t suspect the real reason for the trip.
Scott arranged a private dinner on the beach in the Bahamas, pretending it was just for Mark’s birthday. The waiter was in on the plan and offered to take a video, trying to be discreet, but it was quite obvious.
While they were enjoying the dinner, Scott suggested making a TikTok because the sunset was beautiful. They often made videos like this, so Mark didn’t think anything was unusual. During the video, Scott suddenly got down on one knee and proposed to Mark. It was a surprise and a beautiful moment.
Photo: Heather Kincaid
Cards, Ring and Two Martinis
Cal and Rhi prioritized travel over the idea of settling down, but the unexpected happened when Cal surprised Rhi with a proposal during their 2020 trip to India – a journey that remains one of their favorites.
At the time of the proposal, the couple had just relocated to Australia for a 3-month sabbatical, making their lives wonderfully unpredictable. Rhi, unaware of Cal’s imminent proposal, found herself joking about romantic settings being cringe-worthy during their stay in an incredible Tree House Hideaway near a famous national park in India. Little did she know, Cal had the ring in his pocket and resisted the temptation to propose that very night. Instead, he waited until a week later in Udaipur, where, in a moment authentic to their relationship, they were playing cards, sipping martinis, and Cal popped the question.
Photo: Mitch & Tijana
Through All Trials to the Coveted 'Yes, I do.'
Tatiana and Benedict‘s engagement saga is a testament to the saying, ‘When you know, you know.’ Six months into their journey, Benedict felt the time was right to make the grand proposal. Initially planned for a romantic trip to Dubai in February, he had ordered the ring in November and, for the first time, took charge of all arrangements himself, dropping subtle hints along the way. Amidst unexpected challenges, including a thwarted attempt after a trip to London and navigating lockdowns, the couple eventually found themselves in Lisbon, a city close to their hearts, as this is where Ben first told Tatiana he loved her. When Castelo de S. Jorge was closed, Benedict’s determination led them to climb a fence. Amidst the city’s illuminated beauty, he popped the question, solidifying their love at new heights.
Photo: Andrew Bayda
A Hampton Love Story
The Hamptons became an extraordinary haven for Tom and Kelsey during the challenging times of Covid. Reflecting on that year, they cherish the slower pace that brought them even closer after many years together. It allowed Tom and Kelsey to relish the beauty of life’s little moments, often overlooked in the hustle of the big city. Sharing their first home was a joy, and they embraced every second of it. Tom’s proposal, under a big, beautiful tree at a charming Bed and Breakfast during their final weekend there, marked a magical culmination. With families surprising Kelsey after the heartfelt question, it became the most special and unforgettable weekend, a perfect conclusion to the time in the Hamptons.
Photo: Austin Trenholm
The Proposal During Their Annual 3-Day Hike
During their annual cape-to-cape hike, Brett and Rach’s engagement story unfolds against the stunning backdrop of Yallingup, about 3 hours south of Perth. Brett intended to propose along the stunning coastline with the ring hidden in his pants. However, Rach’s stubborn determination led to unexpected twists, including a close encounter with a deadly dugite snake. Despite two thwarted attempts, Brett led Rach through a bushy, rocky trail to Torpedo rocks in Yallingup on their last night. As they enjoyed a champagne sunset, Brett surprised Rach with a custom-made ring, and amidst the beauty of nature, he asked the question. With a joyful scream, Rach enthusiastically said ‘YES,’ sealing their love in a moment as extraordinary as the sunset that witnessed their engagement.
Photo: Sarah Tonkin
Proposal with Disney Magic
Taj and Morgan‘s engagement in March 2013 was a proposal fit for a Disney-loving fanatic like Taj, unfolding right in front of the enchanted castle for all to see. Morgan orchestrated a day that resonated with a fairy-tale vibe, perfectly capturing the magic of a Disney tale and creating a moment that Taj cherishes.
Photo: Mashaida
In the Heart of the Big Apple
Grace and Peter‘s engagement story is a tale of romance set against the picturesque backdrop of Central Park. Peter orchestrated a surprise proposal on the iconic Bow Bridge during a leisurely walk, with their closest friends and siblings waiting nearby to celebrate the joyous moment. This enchanting location inspired their wedding, as they envisioned the elegance and charm of Central Park weaving through the fabric of their love story.
Photo: Meghan Savage
Back to Origins
Logan and Brytten‘s love story found its roots in the picturesque Ozark Mountains, a destined setting that shaped the course of their romantic journey. Their first date unfolded in these scenic surroundings, where Logan surprised Brytten with a heartfelt proposal, sparking profound conversations and forging an unparalleled connection. Choosing the Ozark Mountains as the venue for their wedding held deep significance, encapsulating Missouri origins and offering a panoramic view of the waters they playfully embraced every summer. With its storied stables atop the Ozark mountains, this sacred location reverently embraced Logan’s passion, standing as the very site of their rendezvous.
Photo:Taylor English
A Scenic Proposal Along the Portugal Coastline
Karolina and Nik‘s proposal story is a testament to the resilience and unwavering determination to face unforeseen challenges. Nik had been planning his proposal since 2019. But this plan was thwarted more than three times due to COVID. Nik’s initial dreams of proposing on the cliffs of the Faroe Islands and later in Africa were foiled. Undeterred, Nik shifted gears and secured tickets to Portugal, a beacon of hope amid uncertainty. Navigating last-minute trip cancellations, Nik declared, ‘We are flying there, no matter what.’
Their journey along the Portuguese coastline led them to the picturesque city of Porto Novo on February 22, 2022. Nik finally proposed in this quiet haven along the Atlantic Ocean, offering heartfelt apologies for the prolonged wait. Their love story overcame obstacles and found its perfect place, waiting just for them.
Photo: Alexandra Gera
Sock in the Safe
In January 2020, Rain’s unusual request set the stage for a unique journey. “Don’t make it a big deal, but can you look for engagement rings?” Rain didn’t entertain a conversation, so Jennifer tried to hold excitement and not ask many questions. Come September 2020, Rain promised a birthday trip to the UK but kept the destination under wraps until they reached the airport. As they were packing, Rain kept suggesting the types of outfits Jennifer should bring, which was different for him to take such an interest in. Mykonos, off Jennifer’s radar due to travel restrictions, became the surprise locale. The only time Jennifer suspected something might be happening was when she saw a rolled-up sock in the safe. The unexpected unfolded in front of the private beach section post-dinner. With Mykonos waves as witnesses, Rain knelt, pulling the ring box from his sock, opening a new chapter in their love story.
Photo: Stephanie Shenton
Magic With the Eiffel Tower as a Backdrop
Rob planned a romantic engagement in Paris for their anniversary with Tara. On the first day, after a delightful wine-tasting experience, Rob and Tara opted for a scenic walk back to the hotel, with the Eiffel Tower in the distance. Rob got down on one knee, but he forgot the ring. Despite the missed opportunity, the following day brought another chance.
Prepared for a mysterious excursion at 7:30 am, Rob surprised Tara by wearing an unusual suit. Expecting to meet a group, Tara led them along the bridge over the Seine. Halfway across the bridge, Rob gazed at the distant Eiffel Tower, expressing gratitude for the 5 years together. Then, he was down on one knee, popping the question. Tara said yes! A hired photographer magically appeared, capturing the heartfelt moment. Afterward, they celebrated with Brie and champagne, cherishing the surprise-filled engagement in the City of Love.
Photo: Sam Docker
A Surprise on the Waves
Justin invited Kim to what she thought was her best friend’s birthday brunch. The unsuspecting bride-to-be was led to a container docked at a marina in Miami Beach. As they approached, the absence of friends and the presence of a beautifully adorned container on the water became the focal point. Justin, cool as a cucumber, dropped to one knee, leaving Kim in shock.
Tying in with the water-themed proposal, the reception space at Mayakoba was also on the water. To continue the narrative, Kim and Justin made a grand entrance at the reception, emerging from a fairytale-like boat adorned with white and pink roses. This unique touch not only incorporated a piece of their proposal but also created an unforgettable and magical moment for the newlyweds and their guests.
Photo: Lauren Alatriste
Breakfast at Tiffany's
The enchanting day began with Lawrence and Poch enjoying breakfast at Tiffany’s Blue Box Café in New York, setting the stage for a surprise shopping spree. Unbeknownst to Poch, Lawrence was covertly gathering ring size information during a visit to Tiffany’s, subtly ensuring the perfect fit for the engagement ring. A romantic stroll through Central Park paved the way to the pinnacle of their love story – the top of the Empire State Building – where Lawrence delivered a heartfelt proposal against the stunning cityscape.
Photo: Kate Roberge
A Secret Proposal for a Jewelry Designer
Joshua, with a clever strategy, used Emmilee’s role as a designer for a luxury jewelry store to create the perfect engagement surprise. A year before the proposal, Emmilee designed her dream ring at work, sharing it with her team, who successfully kept the secret. Joshua, walking into the store, nonchalantly declared, ‘Guys, it’s time,’ and the ring was crafted to perfection.
Amidst the challenges of Covid, Joshua surprised Emmilee with what seemed like a casual, restaurant-style dinner at home. Little did she know, he had orchestrated a romantic setup adorned with flowers, candles, and even their adorable toy Cavoodle, Frankie, dressed in a tuxedo. Unbeknownst to Emmilee, her family was hiding in the house, making the intimate proposal even more perfect.
Photo: Anemotion weddings
Proposal With an Iconic NY View From the Water
Three years into Elise and Richard’s journey, the day after Richard’s birthday became the stage for a heartfelt proposal on his fishing boat in the NY Harbor, with the iconic One World Trade Center as a stunning backdrop. Elise was shocked and said:“If you want to know if I was surprised, all you need to know is that I had my hair in pigtails”. The weekend unfolded in a joyful celebration with family and friends, cruising around Manhattan and toasting to their future with plenty of champagne!
Photo: Berit Bizjak Photography
