11 Real Proposal Stories That Are Making Us Cry ALL The Tears

Photo: Courtesy of Ashton & Jairon Bray.
News flash: The perfect marriage proposal is about more than just putting a ring on it. It should be a thoughtful, memorable, and romantic opportunity to showcase your love and celebrate your relationship. If your partner hates big, showy surprises, maybe don't plan a flash-mob proposal. If he or she loves grand, elaborate gestures, then by all means, go for it.

Ahead, 11 couples share the true stories of their engagements in their own words — from a highly coordinated scavenger hunt that ended with a ring to an oh-so-romantic underwater proposal. Whether you're single, married, or somewhere in-between, these stories are sure to melt your heart.
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Photo: Courtesy of Lindsay & Dylan Raleigh.
Lindsay & Dylan Raleigh
“My fiancé and I live in Chicago, and every year right before Christmas (when the city has cleared out) we spend a day doing cliché Chicago holiday activities. (Think ice skating in Millennium Park, checking out the Macy’s window displays, etc.)

“Last year we decided to visit the Lincoln Park ZooLights. When we arrived, my fiancé was determined to see a specific lighting display at the center of the park. When we reached the display, he talked about how much he loved me, got down on one knee, and told me to turn around. Behind me, in the lighting display was a large group of our friends holding up 'Will You Marry Me?' signs that my fiancé had made using Christmas lights. By that point, a crowd had gathered and everyone cheered as I said yes!”
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Photo: Courtesy of Aire Plichta Reese & Matt Reese.
Aire Plichta Reese & Matt Reese
“I went to a birthday brunch with my friend Sara when she asked if we could stop by the Market Square section of Pittsburgh. I said yes, and thought nothing of it. After we parked and started walking towards the square, we were greeted, to my surprise, by my boyfriend Matt. As we started approaching the middle of the square, I noticed a group of people with their backs to us.

"Matt started to recite a memorized speech of all the reasons he loved me and the people in my life who helped make me this way. When he mentioned the big heart I got from my father, I noticed one of the people turn around; it was my father holding the letter 'M.' At the same time, I heard our friend Mike playing guitar.

"Matt continued with his speech as members of my family and my friends turned around holding letters that spelled out: 'Marry Me.' Our dog, Herman, was also there, in a tuxedo. Our proposal was an amazing day and will always be one of the best of my life.”
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Photo: Courtesy of Emily Taylor & Sofia Corporan.
Emily Taylor & Sofia Corporan
"After Thanksgiving dinner last year, I cornered Sofia's mom and asked her to show me the diamond ring that had belonged to Sofia's grandmother. Grandma Jean was a fancy lady, so the ring had enough diamonds to be reset into two identical engagement rings. With Sofia's mom's blessing, I got Sofia's cousin Ben, a jeweler, to work on the project. Meanwhile, I set the rest of the plans in motion.

"One of my closest friends from college is an amazing artist who makes beautiful animated videos, so we teamed up to make a proposal video. I wrote the script and Shruti spent many hours animating each scene. The video told the story of our relationship, from our first date in my mom's pickup truck to our current apartment in Brooklyn.

"Now, here's where the story develops into two versions — what was supposed to happen, and what actually happened.

"What was supposed to happen: Sofia's sister had made plans to take Sof to see Hamilton. (Fake plans, of course, but it had to be something she would dress up for and would not flake out on.) The night of the 'show,' she would find me at her sister's place, in a suit, with the rings. After the question had been popped, we'd head to our surprise engagement party and eat barbecue with friends and family who had secretly come into town from California and D.C.

"What actually happened: On the Monday before the proposal weekend, people started talking about an upcoming blizzard — a big blizzard — that had D.C. and NYC in its sights. By Thursday, it became clear that nobody would be getting in or out of Brooklyn on Saturday. The flights and trains were canceled, and the party was off.

"So, Saturday evening found Sofia and me in sweatpants, snowed in on the couch. As a Netflix break, I suggested watching a video our animator friend had made, saying that she wanted our feedback. I hit play and my voiceover began. Sofia knew what was happening right away, grinning and calling me sneaky.

"Thanks to nerves, I don't really remember what I said after the video ended (later, she would tell me that she knew something was up before the video, when she reached for my hand and found it clammy), but I do know that in the end, we both asked each other, 'Will you marry me?' I gave her the ring her cousin had designed, the tiny diamonds reset in rose gold, and she gave mine to me.

"A few minutes later, a small group of cousins and friends who live within walking distance arrived, along with fixings for a celebratory dinner. We popped Champagne. Another of Sofia's cousins, Grace, had spent all day gathering congratulatory videos from the family and friends who were snowed out, plus many more well-wishers. Later that night, we took pictures in the snow, which was piled waist-high. And we later learned that the storm had delivered the most snow in the history of New York City.

"At least now we know that at our wedding next summer, we'll be ready for anything."
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Photo: Courtesy of Rachael & Derek Lewis.
Rachael & Derek Lewis
“In December 2012, my then-boyfriend Derek and I took a trip with another couple to New York City (where we now live). On New Year’s Eve day, I woke up to a phone call from one of my best friends. I was a little confused as to why she was calling me so early in the morning, but we chatted a bit, and then she began to read me a letter she said was from Derek. After she began reading, I realized what was happening and started to cry.

"Derek’s letter said that he’d planned my entire day out and that I would be making stops at all my favorite places in New York City. At each location, I would need to call another one of my best friends, who would read me another letter from Derek, and give me a clue to my next destination. (My friend, whom we were traveling with, had the list of what friends to call at each location.) Derek’s letter said that at the very end of the scavenger hunt, he would be waiting for me on one knee.

"By mid-afternoon, I had been to five of my favorite New York places, spoken with my five best friends, and was headed to my final stop (and favorite place in the city): Washington Square Park. When the cab finally came to a stop, I jumped out and ran to the arch, where I knew Derek would be. As soon as I saw him standing there, I started to cry; I don’t remember anything he said. When he finally got down on one knee and asked me to marry him, I was so excited that I bent down to his level and wouldn’t stop hugging and kissing him until he finally got up and made me stop so he could put the ring on my finger!”
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Ariel Moses & Marshall Weinstein
“I’d been dating my now-husband for four years when he surprised me with an engagement that, honestly, nothing could have prepared me for. Marshall is a well-connected DJ and music manager. One of his clients is STK restaurants. I thought we were meeting his parents for dinner; he showed up late and left me in the booth to go check our coats.

"Turns out, he had coordinated a surprise a cappella proposal at STK Midtown, where singers, posing as waitstaff, started to belt out a medley of my favorite songs [and] our songs together to me in a packed restaurant. (I’m a true musical-theater and Glee enthusiast.) This happened right before they led me to Marshall on bended knee.

"Once he proposed, 70 of our closest friends and family burst from a back room where they’d been watching through tinted glass. I was in such shock — it was unbelievable. I even told the singers they were at the wrong table at first, because I had no idea what was going on! It apparently took months of planning, finding, and hiring the right a cappella group, figuring out the medley of songs, timing everything, hiring dancers, getting everyone to fly in, and, most importantly — getting everyone we knew to keep a secret from me the entire time.”
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Photo: Courtesy of Connie Wang.
Connie Wang & Nathan Reese
"My boyfriend and I had discussed marriage at length before the proposal — we were at a point in our relationship where we both REALLY wanted to make the next step. Some might call it unromantic, but I'm the kind of person who could care less about tradition (especially if it involves surprises and the possibility of crying in public). I told him what kind of ring I wanted, and then we both didn't talk about it again; he wanted to be able to make the proposal gesture in his own way, and I was stoked about making a memory about it, too.

"The night before I left for a monthlong sabbatical, I wrapped up a long day at work, picked up a to-go dinner for myself, and got home with a long list of stuff I still had to do (shower, finish packing, book the rest of my hotels, etc.). I had just finished showering and was makeup-less and in my pajamas when my boyfriend came up to me with a ring box. He told me he wanted to do it so I didn't forget him while I was gone, among some other things that are just between the two of us.

"It was one of the most happy and fulfilling moments of my entire life, and I'm so happy it happened so privately and during such mundane circumstances — it's sort of emblematic of the kind of quiet, comfortable relationship we have. Also, every time I get out of the shower now I think about how much I'm loved — that's an unexpected plus!"
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Photo: Courtesy of Heath Tucker & Carlos Avilas.
Heath Tucker & Carlos Avilas
"It all started when one of my good friends called me and said that he had gotten into a rather big argument with his boyfriend. My boyfriend and I were going to be celebrating our five-year anniversary later that night, but I couldn't be the jerk who says, 'Oh, sorry, I'm celebrating how great my relationship is with my boyfriend...but good luck with yours,' so I told him we could meet up to talk it all out. Little did I know this was all part of an elaborate plan to get me out of the apartment so that my boyfriend could work his magic.

"Whilst I was out and about consoling a friend, my boyfriend Carlos was setting everything up on the rooftop of our apartment, which has a great view of the Empire State Building from Long Island City. After I finished dispensing my advice, I headed home to find my Carlos sitting in the stairwell. He was dressed in an adorable seersucker suit, which was already a clear indicator that something was up, because 90% of the time I see him in his PJs. At that point, I began to get nervous. He took my hand and led me up to the rooftop. Upon opening the door, I could see that there was a rather large congregation of people dressed in black. So I was either at my own funeral and he was my Teen Angel, or something else was up.

"As we stepped out of the doorway, we slowly climbed the stairs and moved towards the center of the roof. At this point, I finally realized that it wasn't just some strangers gathering on our roof for some bizarre ritual, but these were all of our friends. Before I could really take it all in, someone started playing a piano and everyone started performing the choreography they had obviously rehearsed — well, some of them had rehearsed. It was very clear who had missed the rehearsal. I soon realized they were performing a mashup of 'Don't Stop Believin'' and 'Marry You,' because who doesn't love a good mashup? Halfway through the song, this group that had their backs to us turned around and it was my family! He had flown them out to be a part of the proposal, and it was at that point that I just lost it. Family tends to have that effect on you when you don't live in the same city.

"They were all holding balloons that spelled out, 'Will you marry me?' Carlos proceeded to get down on one knee, as you do, and I didn't skip a beat with my answer. 'Of course!'"
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Photo: Courtesy of Ashton & Jairon Bray.
Ashton & Jairon Bray
“Jairon's proposal was so beautiful and unexpected that it took my breath away, which is not really something that you want to happen when you are underwater, but I wouldn't change one thing about it. The best part was that he had the whole speech laminated, so I can keep his speech that has been in the Great Barrier Reef forever. He also attached the ring to a necklace so that it wouldn't get lost in the ocean. He thought of everything, and he made our proposal one of the most memorable and perfect moments of my life. He's a Vegas DJ (DJ JBray), so he knows how to put on a show — and he made me the star of it for our proposal.”
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Photo: Courtesy of Ashley Yanover & Marlon LeWinter.
Ashley Yanover & Marlon LeWinter
“Last March, I proposed to my fianceé Ashley LIVE on the Today show. We are getting married this month in Florida, and I honestly cannot wait.

"The engagement took three months of planning. There were three things that were important to me that needed to be part of the engagement; something that could be captured on video (without Ashley knowing about it!), something so unique that no one else could do it, and something where both our families could be a part of it. I knew if I proposed in Florida (where we're both from), she would be expecting it, so it had to be in New York. Plus, this is where we met!

"She had no clue that her parents were even going to be in New York. I tried to build everything around our parents’ schedules. My parents were already scheduled to be up here that week, and Ashley’s brother Josh was on spring break and had been staying with us. Josh’s girlfriend also flew up here that Friday and Ashley thought the four of us would all hang out. What Ashley didn’t know was that her parents also flew up and were staying at the hotel across the street from our apartment!

"You are probably wondering how I got her to Today. I worked with the producer to craft up an email, which I then forwarded to Ashley. Ashley was SO excited when she heard I was going to be in a segment. Her dream was always to be a producer for Today, so just being there was exciting for her. She did NOT want to be on camera for the 'fan of the day,' so I had to work on her for a good hour the day before to convince her.

"The Today staff was unbelievable. They had arranged for cars to pick us up at our apartment the morning of the segment at 6:45 a.m., and a car to pick up our families from the same place at 7:15 a.m. They even put our families into different green rooms on different floors, so Ashley had NO clue. Ashley had called her mom from the green room to remind her to put on Today, and when she got no answer at her parents’ house she called her mom’s cell asking where she was. Her mom said she was walking the dog and that her dad was in the shower. Little did she know they were at 30 Rock two floors below us!

"I was told I would have 30 to 40 seconds for the actual proposal and they would then bring our families inside. The expression on her face was priceless. It was truly the most amazing day of my life. March 7, 2015, at 8:36 a.m. is captured in both of our hearts and our cameras forever."
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Photo: Courtesy of Adam Sechrist & Curt James.
Adam Sechrist & Curt James
"Immediately after our first date, I called two of my best friends and told them that I had just met the man I was going to marry. A little more than a year later, in December 2015, I told Curt I wanted to walk him to work at 8 a.m. on a cold Saturday morning. I think he was a little confused as to why I wanted to get up so early just to walk across Central Park in late December, but he went along with it.

"We stopped by Starbucks for some coffee and then walked to the east side of the park. Curt was telling me some story about a play he was working on, and to this day I have no clue what he was saying; all I could think about was getting him to our spot in Central Park without him realizing something was up. We walked into the park, and I told him I needed to use the bathroom. I left him standing by the Central Park Boathouse and went around the corner to text my friend — who was hiding in the bushes with a camera — that we were minutes away.

"I led Curt up a dirt path behind the boathouse to a bunch of rocks that overlook the lake where everyone takes rowboats in the summer. We came around the corner to our spot, where, a little more than a year before, we had sat with coffee and realized we were meant to be together. We sat down on the rock overlooking the lake, and Curt said to me, 'Wouldn't it be great if we keep coming back here every year, even 50 years from now?' When he turned back around, I was on one knee holding a ring, and I told him I hoped we do come back every year, and asked him to spend the rest of his life with me.

"We both started crying, and he kept asking me, 'Is this really happening, right now?' And while looking around, he saw my friend hiding in the bushes taking pictures, and he asked, 'Do you know who that person is taking pictures? Is a stranger taking pictures?' I said, 'Yes, that's Brooke! Are you going to say yes?'

"Curt said yes, and I slid the ring on his finger; he then put the matching ring on mine."
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Photo: Courtesy of @NYCfitfam.
Jamie Krauss Hess & George Hess
"My husband George and I built our relationship around fitness. Both fitness enthusiasts, within weeks of dating we started hitting the gym, participating in outdoor road races, and taking classes together. It’s been a cornerstone of our relationship ever since. When the time came to propose (we’d only been dating six months, but knew from our first date — it was one of those things!), George approached my 'temple,' Barry’s Bootcamp, for help.

"After our usual 7:10 a.m. class, when the treadmills stopped whirling and with sweat dripping, the instructor said over the loudspeaker, 'Okay, everyone back to their mats…and George, get down on one knee!' The instructor had the ring in his pocket through the whole class, and gave it to George to slip on my finger. The whole class was cheering and taking pics (I saw them show up all over Instagram later, as all these wonderful strangers had become part of our special moment!).

"George had set it up so my mom and sisters would be there to surprise me, and they burst into the studio. I was stunned! Afterwards, the Barry’s staff brought us all protein shakes emblazoned with the words 'She Said YES!' on the side of the cup!

"My mom is Joan Lunden (former host of Good Morning America), so the whole thing ended up in the New York Post the following day!"

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