Which Engagement Story Wins Your Heart? Cast Your Vote!

Engagement Stories collection

Ah wedding season! Nothing warms our hearts quite like witnessing love blossom and thrive. Whether you’re attending a flurry of weddings this season, witnessed the sweetest engagement story or simply following along on social media, there’s something magical about the sweet moments shared between newly engaged couples. 

 

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In celebration of new love, we’re excited to launch our first-ever engagement story contest in partnership with Colonial Jewelers! Whether your engagement happened 10 days ago or 10 years ago, we want to hear your story. People told us about the heartwarming and perhaps even humorous moments when the question was popped and their journey as a couple began. We’ve feature our top six favorite stories here for you, and readers to vote for their favorite. The couple with the most votes will win a $250 gift card to Colonial Jewelers!

 

Read Our Favorite Engagement Stories

Brandon and Elizabeth Engagement Story

 

Elizabeth & Branden

We went to TJ High School and had mutual friends. He asked me to senior prom, but I went with someone else. Fast forward a few years, and I joined an alumni site because my friend encouraged me to before I moved. Guess who found me on the alumni site and lived 15 minutes from where I was moving to in Boulder, CO? We rekindled our friendship and spent a lot of time together but were dating other people. One day, he came by for dinner and told me he loved me while I was cooking. I didn’t speak to him for weeks; turns out, I loved him too, but I was too scared to admit it. He moved in a few months later, and his parents came out for the holidays. His mom and he went shopping, which was odd. So after they flew home, I questioned why they did. He said she helped him pick out a ring. “Wanna see it?” I was dumbfounded. Turns out, he had a plan but couldn’t wait. We called our parents and went out to celebrate. I won out in the end. I gained a stepson, and we’ve shared our days with three of the best rescue pups.

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Bek and Nichole Engagement stories

 

Bek & Nichole

Our love story began in the most unexpected and wonderful way. It all started in an American Sign Language class in college, where we were paired up to demonstrate the concept of a family unit. Little did we know, we were practicing for our future! From the very beginning, I felt a deep connection to Nichole. Early in our relationship, we both knew we had found ‘our person.’ Marriage was something we often talked about, and one day, we decided to go pick out engagement rings together.

Even though we chose the rings as a couple, we agreed not to see the final product until the proposal. When the rings were finished, we even tried them on with our eyes closed! I wanted the proposal to be special, so with the help of my best friend, sister, and an amazing photographer, we planned a surprise at Carroll Creek. Nichole thought we were simply meeting friends, unaware of what was about to happen. I couldn’t resist being a little cheesy—pretending to bend down to fix my sock—when, in that moment, I pulled out the ring and asked her to marry me. Little did she know, everyone was hidden nearby, capturing the entire moment.

This past month, we got married!

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Alex and Kaylee

 

Alex & Kaylee

We were each other’s middle and high school crushes, but we were too scared to tell each other at the time, so we were just best friends who had mutual secret crushes on one another. We confessed our feelings while living in different states. At this point, we’d known each other for 13 years. During one of our visits to each other, two months after dating, we each decided we were sure we had found “the one.” Unknown to each other, we each planned a proposal for the same day. Kaylee had to work, so she left a scavenger hunt for Alex to do throughout the day, including having to message various family members for the next clue. The last clue led Alex to a note telling him how much Kaylee loved him and how much he meant to her, and attached was a ring. The end of the note asked him to marry her. She thought it would take longer than it actually took him to complete it. When she got home from work that night, she walked in to find him down on one knee, asking her right back. They both said yes and marveled at how they both somehow planned a proposal for the exact same day and had no idea the other was planning one too. We’ve now been married over three years and just celebrated 17 years of knowing each other.

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Alex & Chris

We met through mutual friends while riding bikes. I lived in Virginia at the time and Chris was in Frederick. Our first “official” date was a ride along the C&O Canal followed by lunch. We hit it off almost immediately and started dating seriously. We would drive back and forth (2 hours each way) on weekends to see each other and ride bikes together.

After about 2 years of driving 4 hours round-trip, we started talking about moving in together. One weekend, we planned to do a ride on the C&O Canal and parked at the same spot we had on our first date. It was early March and the weather was chilly with a strong wind. A storm had come through the day before so trees were down along the path. Looking back, it was all quite symbolic (overcoming obstacles and all that). Chris asked if I still wanted to do the ride, and I said: Of course! It will be fun! So we headed out along the Canal, climbing over fallen trees as we went.

At the end of the ride, as we made our way back past the aqueduct, Chris asked to stop and get a photo (in the same spot where we took one on our first date). No one was around, so he set up his phone across the way. When he walked over to take the picture, I could see something in his hand. Suddenly, Chris dropped to one knee and revealed a box. The entire ride and faux photo shoot was a proposal! I, of course, said I DO and rode the rest of the way back with a beautiful sapphire ring on my finger.

After our ride, we went out to lunch and basked in our private engagement before calling friends and family to share the news.

That was 6 years ago. Now we both live in Frederick and still ride bikes together often.

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Hayley and Chase engagement story

Hayley & Chase

In the midst of the Covid-19 pandemic in August 2020, Hayley sat on her mom’s guest room bed while visiting her hometown of Calvert County, pondering the possibility of making a Bumble online dating account. After several moments of deliberation, she made the decision and created a profile in hopes of matching with someone. While scrolling through the hopeful bachelors, Hayley stumbled upon a profile with “A nurse would be a plus” in the small bio box. Next to the hopes and dreams was a well-put-together, handsome man with a long-sleeved collared shirt, khaki shorts, brown loafer shoes, a big smile, good hair, a fit body, and a mixed drink with a lime on the rim in his right hand. His profile name read, “Chase.” Other pictures on the profile showed Chase in a helicopter, modeling in a boutique store in Savannah, GA, and memories from attending Florida State University. Hayley thought to herself, “Oh hey, Chase…” and immediately swiped right, opening the gates for this mesmerizing man to send her a message.

Little did they know, they had lived only a county away from each other their entire teenage years and young adulthood, had mutual friends, and never knew each other existed until right then. God’s timing is amazing and always perfect. Many conversations, late-night/early-morning phone calls, and new adventures ignited the new relationship as the two began to fall in love.

Chase slowly became “Daddy” to Hayley’s fur babies, Glacier (Pookie) and Mirah (Mimi) after much persistence. Hayley continued to work as a travel Emergency Room nurse and Chase continued with his cyber security analyst career at Patuxent River Naval Base in St. Mary’s County. On the weekends, their favorite date spot was Baltimore and the two would ride scooters through the city or enjoy one of the many delicious spots to eat. One of Hayley and Chase’s favorite things to do is travel. During the first two years of their relationship, they created life long memories seeing many parts of the world – Nassau Bahamas, Exuma Bahamas, Turks and Caicos Islands, Niagara Falls Canada, New York City, Boston Massachusetts, Savannah Georgia, Detroit Michigan, Charleston South Carolina, Greenville South Carolina, Shenandoah West Virginia, Siesta Key Florida, Bradenton Beach FL, Philadelphia PA, Wilmington Delaware.

A long distance relationship was hard for the two of them but they put in the time and dedication and their love blossomed further. At the end of 2022 Chase moved in with Hayley in Anne Arundel County. Shortly after the start of 2023, they bought a house together. The home was already perfect from the signing of the deed, but the two began adding personal upgrades to it, making it their own special place. During this time, Chase excelled in his career and was blessed with an amazing job opportunity in the Top Security Clearance Sector at John Hopkins Applied Physics Lab while Hayley took a permanent position at an Emergency Room Department in Rockville, MD. With all the blessings God had given them, nothing could be more perfect.

Three years together and there was so much happiness and love built into them. Love is patient and love is kind. Finally, December 16, 2023 Chase created a romantic proposal weekend at the Sagamore Pendry, including a hired photographer that hid in the bushes – in the city where they first fell in love, and Hayley said, Yes! They are so excited to continue their life together through Gods holy matrimony.

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Jordan & Kayla engagement story

 

Jordan & Kayla

As a child, after many disappointments, my dad told me, “One day you’ll know when you’ve found the right one.” I brushed off those words, thinking they were just something a caring parent says to a heartbroken kid. That all changed when I was diagnosed with stage three Hodgkin’s Lymphoma during my first year of college. Suddenly, everything felt uncertain, and those words from my dad took on a new, comforting meaning even after I overcame my battle. Holding onto my faith, I ventured into dating apps to meet new people. One day, I got a notification on Hinge: “Kayla liked your picture.” Skeptical but intrigued, I checked out Kayla’s profile. To my surprise, she was stunning, genuine, and definitely another bot trying to scam me. Nonetheless, I decided to give in to my curiosity and check out this mysterious match.

I went to this “Kayla” who had liked my profile and scrolled through her pictures. My eyes were met with the sight of the most beautiful, humorous woman I’d ever seen in my life, one who certainly wouldn’t have given me this type of time of day in the past. It warmed my heart to see just how much this most recent bot was trying to kidnap me and take my social security number.

What’s more, I saw that this “Kayla” had messaged me! The message read “your cute!”. Without hesitation, I immediately responded “You’re **” because, if this bot was going to waste my time, the least it could do was use the correct form of grammar. My amusement and quick wit were no match for them I thought… Naturally, those feelings instantly sank to my butt when Kayla responded something along the lines of “Wow, I just gave you a compliment and you corrected my grammar?” followed by a laughing emoji standing on its own.

I was PUZZLED, I didn’t know what to say. I had just corrected this person’s grammar… Damn those bots that dulled my senses! Terrified that this beautiful woman would leave (and with good reason), I apologized quickly. I told her about my experience with the app and to my surprise she found my story amusing. We continued to talk! We talked about the app, about each other and our families. It was odd, I’d usually have fallen over my words or tried too hard to be funny but with her, it seemed the conversation would last for hours without us even knowing.

Before I knew it, we’d exchanged numbers, were face timing almost every day and talked constantly. I completely geeked out with her; I showed her my collection of graphic tees, she showed me her Harry Potter magic wands and we even compared our taste in shows and movies. Eventually, the woman who laughed so sweetly when I corrected her grammar officially became my girlfriend.

Fast forward three years and we’d continued to talk about any and everything we could think of, had gone on vacations, gotten on each other’s nerves, and fallen deeply in love. Thanksgiving came around and I knew she was the one woman I could never live without. So, I talked to her family about marriage. Her Mom and grandmother were ecstatic, as they’d seen how we cared for each other and gave their approval quickly. Classically, her uncle threatened to dispose of me without question should our relationship fall apart because of my actions, but I knew his heart was in the right place.

Read the rest of their story on the voting page!

VOTE NOW!

Vote now for your favorite engagement story!

Katy Cawley Headshot
Magazine & Events Manager at Sass Magazine | Related Posts

Katy is an entrepreneur, a social media know it all, and a lover of all the vintage things. She started Katy's Flower Wagon in 2020, having recently sold that business to pursue other creative endeavors. She has been working with Sass Magazine as well as local businesses as a social media manager. You can catch her around town snapping pictures, collaborating with local businesses, and working on all things Sass!
Follow her on Instragram @adventuresinkatyland

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