Alternative titles for this post were: “20 Heart Melting Proposals That Will Make You Feel Again,” and “I’m Not Crying, You’re Crying.”
We’ve had so many stunning proposal images come in at HQ this year that narrowing it down to our top 10 was impossible, so here is our top 20 (in no particular order). Where we can, we’ve included a bit about the couple’s love story, what chance encounter brought them together, what moment was it when they knew they had met their puzzle piece and all the little details (and covert planning) that led up to “will you marry me?” We hope you enjoy it as much as we do. And thanks to all the couples for sharing your stories and allowing our proposal photographers to capture that special moment!
The Eiffel Tower Dream Come True
Elizabeth and Matt in Paris
“Matt and I met online six months ago. We quickly hit it off, I booked a flight on a whim to Newcastle, England where he lives, to meet him. We fell in love, and he came over to Rosemary Beach, Florida to live with me! Once his three months in America was up, we decided to come back to Europe and travel for six weeks.”
The Proposal: “When we first met, I had mentioned that my dream was to someday get engaged under the Eiffel Tower in Paris. I never expected it would actually happen! For the last two months, he threw me off by changing the subject anytime I’d mention getting engaged or marriage. Meanwhile, he and my mom were planning my dream proposal with the most incredible ring (the main stone was from my mom’s engagement ring while the smaller diamonds around it were from my grandmother’s wedding band). As the trip got closer, he suggested we get a photographer (I’m a blogger so it wasn’t a surprise) for a little shoot. I ended up planning the whole proposal without knowing it. I saw Olga’s work online and fell in love with her style and was thrilled that she was available while we were there. Thinking it was just a shoot for some cute Instagram photos, I went casual and wore an old pair of sneakers. The shoot went amazing, and about halfway through Olga asked us to do a pose with our backs turned away. I felt Matt wiggle, and when I turned around he was on one knee. It was the biggest shock of my life in the most magical way! I am so happy it happened the way it did and the whole thing was better than I could have ever imagined.”
All the Little Moments
Rachel and Francesca on the Amalfi Coast
“Francesca and I met at Rollins College and were randomly paired together as freshman roommates and immediately became best friends. Over the course of our college years our friendship grew into love. Love that is unconditional, adventurous and truly one of a kind. Over these past five years we have had many challenges and celebrations, but have always remained united. It is hard to say the exact moment when I knew Francesca was the one because it was a bunch of little moments pieced together. Like the time we got stuck in a gazebo in the pouring rain and just stayed and talked all night, when she made pesto with chicken nuggets from Chick-fil-A to tell me she was going to love me forever, when we brought home our puppy August, and so, so many more.”
The Proposal: “Francesca loves sunsets, the beach, walking through small towns, photography, travel and Italian food. Her family is also originally from Italy, so Positano was the perfect combination of all of her favourite things. I was very nervous for the proposal. Francesca had been hinting for months about the ring she wanted and getting married, so I was almost positive she would say yes, but it was still terrifying. When we got to the proposal spot near the beach in Positano I told her that I wanted to spend the rest of my life with her and continue our adventure together then asked, ‘Will you marry me?’ She said yes!”
That Santorini Sunrise
George and Sara in Santorini
The Proposal: George surprised Sara with a ring right in the heart of Santorini’s Oia Village just as the sun was coming up. Oia is one of the most picturesque villages on the island, with stunning views of the caldera, white-washed houses and the famous blue three-domed church—it was the perfect spot for a special proposal.
Starting the New Year Off Right
Jamil and Meryem in Lisbon
“Meryem and I met in Hong Kong. She had been living there for several years and I was in the second year of a temporary work assignment there. The first time I saw her she was sitting at a table in the back of a small bar that was directly across the street from my flat. A conversation turned into an impromptu night out that turned into several trips together that I never wanted to end. So I had to make sure it turned into a lifetime together.
“We travelled to Morocco to spend time with her family between Christmas and New Years. We wanted to add a destination to the trip since we love to travel. It is hard to find a place that neither one of us have been so we chose a place that Meryem loved and I had never experienced. Once we booked the trip and I knew that we would be celebrating the New Year in Lisbon, I wanted to propose on January 1 to start the year off right.”
The Proposal: “We work up early to embark on our “Moorish Architecture Tour” starting at Belém Tower (or at least that is what Meryem thought). We arrived at the tower a bit after sunrise and the sky was beautiful. Once we were in position I got down on one knee and began professing my love for her….only she took two steps back. Me being conscious of the prior directions given to stay on my knee as long as possible for the photographs, I stopped professing my love and asked her to come back here! So instead of continuing to recite the best proposal ever (slight exaggeration) I began to ask Meryem several questions: ‘Can you stand still?’ ‘Can you look at the ring?’ ‘Did you say yes?’ Fortunately she clarified that she did say yes, but does not remember any of the prior discourse.”
The “It’s for Christmas Cards” Ruse
Robert and Patrick in Washington, DC
“So we met online in January 2017, but quickly realized that we had lived across the street from each other in college for three years and somehow never met each other! So we have many friends in common and quickly grew close. He lived about 40 miles away for the first year and a half of our relationship, but we actually moved in together this past July. We have enjoyed travelling together since we started dating and some of our favourite photos are from our trips together. We had a couple friends who actually used Flytographer in Venice a few months ago and told us how great of an experience they had taking vacation photos. We had a trip to DC planned already and I asked Patrick if he would enjoy getting some vacation photos taken since we had just moved in together and we could use them to spruce up the new apartment and maybe send out Christmas cards! He thought it was a fun idea and we continued under that premise while I was planning the proposal with Flytographer behind the scenes.”
The Proposal: “The Shoot Concierge and photographer were both a huge help in getting all the details nailed down and it went off without a hitch! They actually came up with the idea to have us back to back and then me to get down on one knee.”
The Case of the Double Ring
Juliana and Tatiana in Santorini
The Proposal: “I began planning my proposal to Tati months before we embarked on our trip to Greece. I knew this moment had to be perfect. I hired a Flytographer and began looking for the ring. Once I found the ring, I was informed the ring was no longer available and there were only two left. I was in a bidding war with a stranger, who happened to be Tati, for the SAME RING! After a few weeks of going back and forth, the ring arrived to the house. I asked Tati’s mom to hide the ring for me, without knowing Tati had asked her to do the same.
“Fast forward to our trip… We arrived to Santorini, I anxiously waited for Friday the 7th to approach. I kept reminding myself to play it cool so Tati wouldn’t catch on. The day had arrived, throughout the morning I kept insisting that we head back to the hotel in order to freshen up and head over to the Skaros Rock to see the sunset.
“We arrived to the location two hours before the set time I had arranged with the photographer. We chose to head over to a rooftop bar and grab a few drinks until it was time to head down to see the “sunset”. It was time…… The photographer texted me saying to start making our way down slowly. With every step I took my heart began to palpitate vigorously. I needed this moment to be everything she ever dreamed. We reached the chapel in front of Skaros Rock, Kimonas (the Flytographer) was there pretending to be a tourist and waiting for my cue to approach us. I asked Tati to take a selfie with me to signal Kimonas to come over. He asked if we would like him to take a picture of us on my phone, then shortly after asked if we would like him to take a picture with his camera and I rushed to say yes. I quickly put my fanny pack on the side and tried to put the ring box in my back pocket without Tati noticing. We got into position for the picture and that’s when I looked at her and said, ‘You know I love you, right?’ Tati immediately caught on and asked, ‘Wait are you proposing right now?’ I kneeled down and said, ‘Yes, will you marry me?’ She quickly reached into her purse and pulled out a box and said, ‘Only if you marry me.’”
The Italian Job
Adam and Lauren in Cinque Terre
“Before I met Lauren, she was able to visit the Cinque Terre for a day and bought a painting on the street in Vernazza. This painting was captured Vernazza’s harbour beautifully and she’s been obsessed with the city ever since. I had it framed for her as a Christmas present almost two years ago around the same time we began discussing the possibility of a return trip to Europe. Immediately after deciding to plan a trip, I decided I’d simultaneously plan my proposal, so we could get engaged in the painting and have it as reminder.”
The Proposal: “The day before our first full day staying in Vernazza, I told Lauren that I had scheduled a surprise trip to a local vineyard. This is something we might do anywhere and served as a good excuse to have her hair, nails and makeup ready early in the morning. Immediately, she peppered me with questions about whether to pack a bag and what walking would be like and what the vineyard looks like. I researched an actual vineyard in Monterosso and quickly used that to facilitate the lie.
“The following morning, after seven days of travel through two other countries, she wakes up early in preparation ‘to meet our vineyard tour guides at our pick-up point in Vernazza harbour.’ The only initial snag was placing the ring and box in my back pocket before brushing my teeth that morning. Lauren kindly reminded me to brush my teeth and had to scramble up a plan to get across the studio apartment without her seeing this mountain sticking out in my pocket. I motioned across the room for her to grab her hat and rotated clockwise simultaneously, so I could back into the bathroom and we were back on track!
“We walked down into the harbour, which was still quietly preparing for a day of tourism and I didn’t immediately see [our Flytographers] Ramon and Sonia. We had planned for them to be out taking pictures of the city before our arrival and we would stumble upon them and ask for a picture. As soon as I start to panic slightly, I hear a whistle from the main street of Vernazza. Ramon and Sonia were moving towards us while rotating around taking pictures of the buildings and each other. I immediately sent the signal for them to approach us (we took a selfie with the church behind us). As Ramon gets close, I ask him to take a picture of us with my phone and then he offers to use his professional camera. After one click, we were re-positioned and I drop to a knee. The rest is a storm of tears, giggling, a ‘Yes’ and a premature snatching of the ring, only for me to reclaim it and place it on Lauren’s finger in traditional fashion.”
It Had to Be Venice for Veneziano
Wagner and Monika in Venice
“Deep down, I think I’ve always known Monika was the one from the moment I met her. I would always introduce her to family and friends, and later in private I would say I had a feeling she would be the one. My last name is Veneziano and I couldn’t think of a more perfect place to have this proposal.”
The Proposal: “It’s such a romantic city and it made the proposal incredibly magical! As rare as it sounds, the proposal went exactly as planned! I told Monika we were going to one of my favourite restaurants’ in Venice for dinner. Obviously, there was no restaurant and we were actually headed to this beautiful bridge where the proposal took place. When we arrived at the bridge, our Flytographer was ready to go, so I went down on one knee and the rest is history! It was absolutely beautiful!”
The First Date That Almost Didn’t Happen
Paul and Justin in Honolulu
“Justin and I met online about 18 months ago now. How thoroughly modern! Our first date very nearly didn’t go ahead due to work related commitments etc. Then suddenly those plans all cancelled and I jumped at the chance of making that date happen. Happily Justin was also free that night. I knew from the moment he walked around the corner that evening that he was the one for me and this was going to be something special. Just how special, I could never have guessed. So, then when he’d gotten under my skin and into my heart, I said to myself, ‘It’s now or never…’
The Proposal: “I realized that if I was going to make this proposal memorable, it had to happen in Honolulu. After doing some searching and discussion with Maria and Trevor from Flytographer, we decided on the magical Makapu’u Lookout as it’s both spectacular and reasonably private at that time of day. The Big Day: Given that both our parents live interstate from us, and given that I was intending to pop the question while overseas, I knew that I wanted someone there to capture the moment on film. The trick is, how would I give the photographer permission to be close enough to ‘get the shot’ while not giving away the intent to Justin? This is where, together with Maria and Trevor we agreed that to lure Justin to the location I’d tell him that this was a vacation photography shoot being offered by our hotel. It’s SO not my style, it should have been a red flag, but he bought it (or at least he lets me believe that!). Trevor suggested that he’d tell Justin he wanted to get some individual shots and to face the ocean. Meanwhile I’d get into position to ask the big Q. And, that’s exactly how it went down. To the letter. I love it when a plan comes together! There are moments in life which will be etched into a person’s memory for the rest of their lives — this was one of those for both JJ and I.
Don’t Cry Over Spilt Tea
Luke and Bonnie in Mauritius
“We met for a cup of tea four years ago on a blind date. We instantly clicked and knew we were meant for each other after Bonnie spilt her cup of tea everywhere and 10 minutes later so did I! We have spent the last four years working hard and travelling together, creating amazing memories, and we love the way we compliment every part of each other!”
The Proposal: “Once the sun was on the perfect angle, [our Flytographer] Mayline told us to go back-to-back, then said, “Wait there, I’ll just fix your shirt, Luke.” She then handed me the ring whilst Bonnie’s back was still turned. Mayline gave the signal, “this is perfect,” and then I turned onto one knee and asked for Bonnie to turn around. Mayline then caught the entire beautiful moment on camera and then continued to capture more after while we were both still so excited and in the moment. We will now never forget this for the rest of our lives.”
A Fast and Furious Love Story
Benjamin and Lettie in Florence
“My fiancé and I met at a bar. We were both there with friends and suddenly my friend came up to me to tell me we were leaving. But I noticed my friend talk with a girl he had met so I stuck behind and was just hanging out on my own. I am 6’5 and can see over most of the bar and my fiancé is 5’7, so she is fairly tall as well. All night I had been making eye contact with her, but was too afraid to go talk to her. Finally her roommate whom she had know for only two weeks walks over to me, introduces herself, and then says, ‘This is Lettie’ and walks away. The bar was crowded and loud and I wouldn’t hear her name. Finally after a minute of me still not understanding she said, ‘Lettie, like in Fast and the Furious.’ I replied, ‘Ohh, do you like to drive really fast cars?’ She replied, ‘No.’ At that point I figured I blew it, but we talked the rest of the night and the rest is history.”
The Proposal: “Lettie studied abroad in Florence seven years ago and hadn’t been back since. Her favourite spot is Piazza Michelangelo. I knew proposing at that spot would mean the world to her.”
Transported to Another World
Justin and Kristen in Kyoto
The Proposal: The Arashiyama Bamboo Grove is a particularly special place found on the western outskirts of Kyoto. The whole Arashiyama area is a nationally designated Historic Site, so its Bamboo Forest has been well protected, and for good reason. Walking through the towering bamboo trunks in the green filtered light, feels like a whole other world. Justin and his fiancé-to-be Kristen were visiting the Bamboo Grove on a trip and had rented kimonos. To capture the moment, they hired a photographer, (obviously a Flytographer in disguise) and Justin surprised Kristen with a proposal, right amongst the bamboo in beautiful Kyoto. “Coo is an amazing photographer! His knowledge of the photo location really helped with the proposal, and it went perfectly.”
A ‘Luck of the Irish’ Surprise Proposal
Jordan and Chandler in Dublin
“We met in Denver, Colorado when Chandler had just moved for graduate school. Immediately we were friends, and quickly after we attended a NHL Colorado Avalanche game, where we hugged while greeting each other, we both felt like we had been friends for years. We both knew at that time that we complimented each other perfectly and we had so much fun with each other, we were inseparable shortly after.”
The Proposal: “Jordan’s family has heritage in Ireland, and he had travelled there before with his entire extended family, his grandparents showing them the country. My grandmother had travelled there and it was her favourite destination, so I had always wanted to go. We both lost our grandparents in the last couple of years, so Jordan surprised me for Christmas in 2017 with the trip! The Big Day: We walked around the city of Dublin early in the morning, so there weren’t many people out and about. With it being my first trip there, I was totally captivated by the architecture and the charm. Jordan told me we were walking to breakfast, so we ventured out where we eventually began to trail [our Flytographer] Vanessa (unbeknownst to me) and she led us to the perfect alleyway. I had no idea until the moment it happened, and it was the best moment of our lives!”
Harry Potter Fans, Eat Your Heart Out
Saket and Nupur in Banff
The Proposal: After a helicopter ride up into the mountains in Banff, Saket got down on one knee and surprised Nupur with an engagement ring inside a golden snitch. Both the ring and its special snitch ring “box,” the latter you might recognize from Harry Potter, were made by the couple’s friend who is a jewelry designer in New York. Saket, in the game of quidditch (and love), you win!
When One Door Opens
Armando and Valeria in Chicago
“A Colombian girl moved to Mexico and met a neighbour that helped her to open a door and then he made her feel in love with his country and his heart. Now they are engaged!!!”
The Proposal: “It was perfect!!! We feel very connected and our engagement day is the best beginning of this journey that we are starting, and what can be better to keep all our memories in than this amazing photo shoot?”
The Big (Lavender Field and Serenade) Gesture
Samuel and Lu in Provence
The Proposal: “Andrea and Cyril were simply amazing. They were true professionals and went above and beyond for our engagement. I had hired a string quartet for the occasion and she offered to coordinate the entire event. Everything went perfectly.”
Back to Where They First Met
Bram and Tania in Cape Town (Tania is actually a Flytographer in Amsterdam!)
“We travel to Cape Town a few times a year for work, it’s a very special place for us. We met there a few years ago, so proposing in Cape was the most logical thing for me.”
The Proposal: “Lots of funny things happened on the way, keeping it a secret was a challenge, but everything turned out perfectly. Alicia did a great job in keeping a secret and capturing the most important moments. Everything was so nice: the light, the setting (one of our favourite spots in Cape Town), and the moment itself.”
Love at First Hi
Clinton and Bailey on the Oregon Coast
“I knew from the second I met her that she was the one…that sounds cheesy, but it couldn’t be more true. I was just in shock she agreed to go on a date with me!”
The Proposal: “Oregon was on our bucket list and I thought, what better place to pop the question? The proposal was such a blur! I was so nervous and excited I could barely remember everything leading up to being on one knee. Nothing went exactly according to plan but having a detailed plan in place kept me somewhat on track!”
“Sometimes the Puzzle Piece Just Fits”
Jeffrey and Naomi in Amsterdam
“We both moved to NYC after college and met on a dating app. After a few dates getting to know one another, we found we were highly comparable with one another in a way neither of us thought possible. Sometimes the puzzle piece just fits. To this day we’re surprised we found each other.”
The Proposal: “Although we both love the outdoors, we absolutely love cities. Amsterdam not only looked like a beautiful location to propose, but we both fell in love with the city the instant we stepped foot in it. We booked a trip that started in Amsterdam, and it’s fun and unusual urban vibe made this the perfect location for us. This wonderful destination will forever hold a special place in our hearts.
“After a full day of exploring, including a walking tour, Dutch pancakes, exploring the market in De Pijp, and a drink at a De Tulp, we went back to our Airbnb to freshen up before dinner. On the way to the restaurant, we made a pit stop at Magere Brug, or the skinny bridge, to take a photo. Next thing you know, we’re engaged!”
A Tale of Two High School Sweethearts
Marcus and Indiara in Paris
“Indiara and I met in high school our junior year and started dating our senior year. One day while still in our teens and in high school I jokingly said ‘Let’s go to the courthouse and get married.’ I knew she was the one when she looked at me with those big brown eyes and replied with ‘OK, let’s do it.’ After going through a round of ‘are you serious?’ I told her if we were still together in ten years then we will get married. Fast forward ten years and here we are.”
The Proposal: “We’d been planning a trip to Paris for a couple of years and I knew wanted propose in la ville de l’amour! It would make our trip even more intimate and memorable. Of course my initial plan was the Eiffel Tower in the background for that iconic shot that everyone loves. I searched and read stories of other proposals and saw a couple of shots in the Tuileries Garden. This location stood out to me because of the how the tree line puts a focus on the couple and you get a beautiful shot of the Louvre in the background. Since the Garden leads up to the Louvre it makes for a perfect location to get shots there too.”
