Our 22 Favorite Proposal Stories From Real Weddings

Missing a Key Element

After DeYandré Thaxton and Vishal Reniguntala met on OkCupid and had their first date at the Museum of Contemporary Art Chicago in 2017, the pair knew their connection was something special. “Our first date was the only time I asked for a second date during the first,” Vishal admits. “I was excited to see her again, and I had a feeling it was mutual.” 

Three years later, Vishal was absolutely certain DeYandré was the one. The duo visited DeYandré’s family in Boston over Thanksgiving, and during that trip, Vishal asked DeYandré’s mother for her daughter’s hand in marriage. His initial plan was to propose after Christmas, but he decided, “I didn’t want to wait. I wanted to propose before I flew out. The only thing missing was an engagement ring.” 

Vishal immediately headed over to the mall and bought a silver ring for the time being. “I was super nervous, second-guessing if my plan was good enough, if the timing was right, and if she’d be okay with this ‘placeholder’ engagement ring,” he reveals. It ended up being more than enough. After Vishal proposed to his love, she declared “yes,” and they celebrated with Champagne. “It was such a special moment, especially with my entire family present,” DeYandré reflects.

A Grand Gesture

Zoe Win Shewer had just relocated to San Francisco for work when her chance encounter with Sameh Elamawy occurred. “I was with an acquaintance getting coffee, and she mentioned that her friend Sameh had cut a trip short and was going to meet us in the park,” Zoe imparts. “The rest is history.” 

Three years later, Zoe traveled to London for a girls’ getaway. While walking through Hyde Park to meet her best friend, a couple asked Zoe to take a video. After Zoe pressed the record button, the man got down on one knee, so she assumed she was watching someone else’s proposal. Suddenly, the couple started singing, and more and more people joined in. Then, Sameh appeared. As it turns out, Zoe was witnessing her proposal. One successful flash mob later, and the duo was engaged!

One Surprise After the Next

Toral Vaidya and Raj Chimanji have known each other ever since Raj was roommates with Toral’s brother in college, but at first, they kept things friendly. It wasn’t until eight years later that they reconnected and started getting romantically involved.

Four years into their relationship, Raj surprised Toral with a trip to Amangiri. “As we were checking into the hotel, the resort staff recommended stopping at a scenic viewpoint,” Toral recalls. “A few minutes into our walk, Raj proposed. It was all truly a surprise—the trip, the proposal, and the ring.” After sharing the news with their families, the couple decided to turn off their phones for the next 48 hours, so they could truly savor the moment. “It was the trip of a lifetime,” Toral reminisces.

A Scenic Spot

For Victoria Dickerson and Zachary Morton, it all started with a text. It was Victoria’s first day on the job at a financial planning firm where Zachary worked, and she decided to reach out. After three weeks of regular texting, Zachary asked Victoria out on a proper date. From there, things moved quickly. Just six weeks into their relationship, the pair said “I love you.”

Five years later, in November 2020, the couple was planning a getaway to Paso Robles, California. Victoria had a suspicion something magical was bound to happen after Zachary instructed her to get her nails done. “I had always warned Zachary that I didn’t want to get engaged without a fresh manicure, so I could show my ring off,” she explains. “Deep into the pandemic, it had been a while since I set foot in a nail salon, so I knew something was up.”

She was right. While the twosome was admiring wine country from the top of a hill at Calcareous Vineyard, Zachary got down on one knee. Victoria was ecstatic, and they relished the moment with a photo shoot and an Italian dinner.

Popping the Question at Home

Although Tracy Akufo and Adam Totman worked together as teachers at an elementary school in 2015, they hardly exchanged a word. It wasn’t until the following year, when they attended an outdoor music festival together, that they got to know each other. Tracy offered to give Adam a ride home, and they were surprised at how easily their conversation flowed. “Adam invited me to his 25th birthday brunch, and after a date or two, we were inseparable,” Tracy remembers. “Being together felt natural, and there was never a dull moment. Our playful spirits and appreciation for the simple joys of life were present in our everyday work and lives, which made it somewhat easy to fall in love,” Tracy explains. 

Adam was planning on popping the question in front of the Capitol Building one afternoon in November 2019. The area turned out to be overwhelmed with tourists, so he decided to wait until they returned to their apartment. “Confessing his desire to make me his wife in the privacy of our home, where we could be our most authentic selves, was more than I could ever ask for in a proposal,” Tracy gushes.

A Hidden Agenda

Although Jennevy Opena and Cipriano Macabuhay had many mutual friends, it wasn’t until a friend’s birthday party in April 2007 that they officially met. Cipriano was smitten from the start, and the pair dated for a decade before getting engaged. Since the duo dated for such a long time, Cipriano knew exactly how to surprise Jennevy. “He planned for my friends and I to go on the Malibu Wine Safari in August of 2017,” Jennevy recalls. “I’d wanted to go forever and thought it was going to be a great day trip.”

After introducing the group to the resident wildlife, the tour guide led everyone to a private overlook of the vineyards. Much to her surprise, Jennevy found a flower crown, balloons, and a handwritten letter from Cipriano, but Cipriano was nowhere to be found. “As I was reading, he snuck out from his hiding spot and proposed,” she exclaims. “It was an amazing surprise, and I was surrounded by my closest friends."

Kicking Off the New Year

For years, Gabrielle Korn and Wallace May were acquaintances until Wallace finally took the plunge and asked Gabrielle out over DM. Fast forward to New Year’s Eve right before 2020, and Wallace had another question. “At dinner that night, Wallace asked Gabrielle if she had any New Year’s resolutions,” they relay. Gabrielle said she needed more time to think about it, but really, she saw it as the perfect opportunity to delay another very important question. Once they got home, “Gabrielle asked Wallace to come sit down and said she was ready to share her resolution,” they continue. “She’d put the ring between the couch cushions, and after fishing around for a few seconds, gave a little speech and asked Wallace to marry her.” 

A Worthwhile Change of Plans

Susan Nugraha and Eli Klein dated for two years before Eli concocted a plan to propose to Susan at Sushi Yasuda in New York City. “We stopped by his mother’s apartment on our way to dinner, and while I was in the bathroom, he showed her the ring,” Susan explains. “She convinced him to propose right there in her living room!” Although Eli's original plan didn't happen, it ended up being fate. The next day, Eli's mother was diagnosed with terminal cancer, and she passed shortly after. “If we could do it all again, we wouldn’t change a single detail of that special night,” Susan declares.

Sounds of the City

Alicia Cabra first met Alvaro Sierra Lopez at a Halloween party in 2013, and she developed a crush on him that very night! Alicia held onto this feeling for nearly six months before she and Alvaro officially started dating. “It was May of 2014, right around the Champions League final, when we fell in love,” Alicia remembers. After a few years of dating, the couple traveled from Madrid to Paris, heading up to Sacré Coeur to take in the views of the city. “There was a boy playing guitar, surrounded by a huge crowd,” Alicia describes. “He started to play "Pretty Woman," and that’s when Alvaro grabbed my hand, and I realized he was on his knees asking me to marry him!”

A Serendipitous Moment

Robyn Iglehart was waiting in line at the airport when Stephen Ross offered to carry her luggage. The two ended up sitting next to each other on the plane, and their connection was so strong that it turned into a full-blown romance. A year and a half later, the duo took another trip—this time together—to Italy. To Robyn’s surprise, Stephen got down on one knee and popped the ultimate question.

“After I accepted his proposal, 'At Last' by Etta James began to play in this small and lovely Italian restaurant,” Robyn illustrates. “It happened to be one of the favorite songs of my late mother and his late grandmother. We both saw it as a blessing from heaven and a sign of acknowledgment.”

Coming Full Circle

Spending time in the great outdoors has been a pivotal part of Olivia Pei and Graham Keggi’s relationship. The duo met in 2015 through mutual friends while skiing in Lake Tahoe, so it was only fitting that their engagement was equally as adventurous. Exactly five years later, Graham asked Olivia for his hand in marriage, and it brought the pair back to their roots.

“He proposed atop a mountain in Banff while we were skiing,” Olivia recounts. “He has some flair for the sentimental in that way.” They celebrated in the most apt manner. “It was very exciting because right afterward, we got to ski down the mountain,” she elaborates. 

A Road Trip for the Books

With a wedding in the Spanish countryside, a legal ceremony in London at the Old Marylebone Town Hall, and a spiritual ceremony on top of a mountain in Andalusia, it only made sense that Gayle Noonan and Tatjana von Stein got engaged in a similar globe-trotting manner.

"We had just bought a classic BMW convertible and decided to take it on its first road trip,” Gayle says. “We arrived via a hidden track through unruly fields of sheep to discover a piece of paradise run only by solar energy.” They grabbed their swimsuits, popped open a bottle of red wine, and headed out for a stroll. “We both knew life couldn’t be more perfect,” Gayle reminisces. It was so perfect, in fact, that both Gayle and Tatjana were plotting a proposal, but Tatjana beat her to it. The answer was "yes," of course. “We spent the rest of the day repeating the question and the answer to one another,” Tatjana reflects.

Proposing With the Perfect Backdrop

Venus Et Fleur founders Seema Bansal and Sanjam “Sunny” Chadha first met when Seema was visiting a friend in New York City in December 2014. They decided to pursue a long-distance relationship, but after six months, Seema moved to Manhattan to be with Sunny permanently. Three years later, while the twosome was visiting Paris, Sunny proposed to Seema on the terrace of a suite at the Shangri-La Hotel with the Eiffel Tower in the background. "I tagged him in a photo on Instagram when we first started dating, telling him, 'This is exactly where I’d like to be,'" she reveals. "He never forgot that and re-created it for the proposal."

An Elaborate Display

When Nicole Thomson was a bridesmaid in her friend’s wedding four years ago, she never expected to start her very own love affair with the videographer, Gregory Ross Fisher. “Once we started talking, we just couldn’t stop,” Nicole exclaims. Her own happy ending came in August 2019 when Gregory proposed. “I came home from work, expecting it to be a normal date night out with Gregory, grabbing a ride downtown,” she says.

Instead, Gregory transformed their backyard into a romantic oasis, where Nicole walked into “the most extraordinary, beautiful display: a candlelit table, velvet tablecloths, flowers, market lights, tiki torches, wine glasses, and the most amazing catered private dinner.” It was the perfect spot for their intimate engagement and made saying “yes” much easier!

Staging a Photo Shoot

Tara and Brian Lehrer instantly hit it off when they met at a party during their sophomore year of college in 2008. Their connection was so strong that they talked all night—until Tara's 8 a.m. class! "We pretty much started dating instantly after that," she says. "We've been together ever since." Nine years later, the couple commemorated their anniversary with a getaway to Cambodia, and Brian saw it as the prime opportunity to propose. Tara had told Brian that she wanted to take more pictures of him on the trip, so once the two arrived at a wooden bridge amid rice patties, he broke into a series of silly poses. For the last shot, Brian got down on one knee, played their favorite song on his phone, and pulled out a ring. After Tara screamed "yes," they spent two hours crying of happiness. "It was the most magical, surreal, and incredible feeling of all time, especially being totally alone in that moment together in that setting," Tara notes.

Capturing the Holiday Magic

Self-care blogger and speaker Aisha Beau Johnson was tricked into going on a blind date with David Brandon Frisbey, but it ended up being the best case scenario. “I walked in, and David had a huge grin on his face,” she describes. “His energy was magnetic, and the rest was history!”

While the couple was on a trip in Bal Harbour three years later, David was planning on asking Aisha to marry him, but the rain interfered with his original plan to propose outside. “As I soaked up in the tub in our suite, he was frantically running around the hotel trying to find a good spot,” she remembers. “He told me he was looking into a car to bring us dinner.” After a while, they headed downstairs to grab drinks before dinner. "We walked past a beautiful Christmas tree in the lobby of the hotel, and as we admired it, he turned around and got down on one knee,” Aisha says. “My heart was racing, and he barely got the words out before I yelled, ‘Yes! Yes!’”

A Nautical Nod

When Adam Londy proposed to Claire Abramowitz the weekend before Valentine’s Day in 2017, she had no idea it was coming. “I love to scuba dive and nerd out on all things marine biology–related, so I wasn’t suspecting a thing when Adam took me to the Aquarium of the Pacific in Long Beach, California,” Claire admits. They wandered the exhibits and paused to watch the seals and sea lions before Adam insisted they head to the coral reef exhibit. The diver delivered a presentation and noticed that a piece of trash had made its way into the tank. “She swam over to grab it and came back with a big orange sign that read, ‘Two less fish in the sea... Claire, will you marry me?’” she recounts. “Everyone was cheering, and I immediately started to cry!”

Straight Out of a Book

Jessie Cai and Phil Comerford’s love story started digitally—but not on a dating app. “We actually first traded emails back in April 2010 when I was trying to sublet Phil’s apartment for the upcoming summer,” Jessie shares. Nearly 10 years later, the pair got engaged.

“We love to travel, and Phil prepared a photo book of all our travels together over the past 10 years as a belated 30th birthday gift,” she says. “The last page of the book, which had a decade’s worth of memories as well as letters from my parents, sister, and friends, was a note asking if I would be his forever travel buddy.”

A Handwritten Note

Australia-based pair Caroline and Courtney Smyth-Lace have their careers in nursing to thank for their fated union. The pair met when Caroline transferred to the same cardiology ward as her future wife in 2011, and they started dating two years later. In 2017, after Caroline returned from her grandmother's funeral in Ireland, the two celebrated their reunion by enjoying a picnic of cheese and Champagne on the beach in Sydney. Courtney pulled out a letter, which she claimed had arrived during Caroline's trip, but which was actually a series of flashcards leading to a proposal. Caroline grabbed the letter and accidentally opened the bundle backwards, reading the final proposal card first. She looked up to see Courtney holding a ring box, and the rest was history.

Celebrating Multiple Milestones

After exchanging a few messages on the dating app Coffee Meets Bagel, Jasmine Owens and Glenwood Barbee finally met in person over dinner and drinks. Their first date went so well that Jasmine turned to Glenwood and asked, “So, are we going on a second date or what?”

Four years and countless dates later, the pair received the keys to their first home together. While taking photos in front of the “Sold” sign on their new property, Glenwood decided to pop the question. “I knew this was the first thing I wanted to do in our new home,” he discloses. Jasmine enthusiastically accepted, and they toasted their engagement and new home with Champagne on the back porch.

A Sensational Sunset

It was fate when Steph Taddei and Tim Goger met out on the town of New York City in 2012. The two developed a friendship, but after getting to know one another, they discovered a spark was present. Six years after their first date, the duo set out on a two-week vacation through Italy and Greece. “During our drive from Naples to Positano, Tim suggested we catch the sunset and grab some drinks at the beach before dinner that evening,” Steph imparts. “There’s nothing I love more than a good sunset, so I was pleasantly surprised to hear he was thinking that.”

The two planned on leaving the hotel at 6 p.m. sharp to catch the sunset. Oblivious to the proposal, Steph arrived 30 minutes late while Time tried to remain calm. “As the sun was setting, we made our way over to a good spot, snapped a couple of photos, and before I could blink my eyes, Tim was down on one knee saying, ‘This is the real reason we’re here,’” Steph reminisces.

Pulling Off a True Surprise

Although We Met at Acme host, Lindsey Metselaar, and Steven Greene were mutual friends for years, they never exchanged more than a few pleasantries. That all changed on New Year’s Eve right before the start of 2020. “He majorly hit on me,” Lindsey remembers. When a global pandemic emerged two months later, the two quarantined together and became serious very fast. 

At the end of the summer in 2021, Steven knew he wanted to propose. “He was very traditional about it, which I love,” Lindsey shares. “He went over to my house when I was away, brought my parents dinner, and asked them for my hand.” A month later, Lindsey was getting ready for dinner when her friend Ryan called. Lindsey grabbed Steven and told him they had to meet Ryan at the lake, but once they got there, Ryan was nowhere in sight. “I got out my phone to call home,” Lindsey continues. “Steven took it from me, got on one knee, and said, ‘Ryan’s not coming.’ I was truly in shock for the first time in my whole life!”