Real Proposal Stories

Real Proposal Stories

What’s better than a good ring photo? The love story that goes behind it. And we want to hear yours!


The I Said Yes by mywedding Photo Contest is the best way to show off that new sparkle to your friends and family. Plus, what newly engaged couple wouldn’t love to win an $850 Visa gift card for a little financial help in planning their happily ever after? You might want to grab a tissue for these sentimental and thoughtful engagement stories because we’ve collected five of our favorite proposals for you to swoon over. Enjoy!


Caitlin: For all of my life I have dreamed of becoming an attorney. Currently I am a law student and my fiancé has supported me in my pursuit for years. As a book nerd, I am completely obsessed with having a well-stocked library one day. We visited an antique store a couple months ago and saw hundreds of law books being sold. I was so excited, but knew I could not buy them for my small apartment. Secretly my fiancé returned to the store and purchased over 600 of those exact books. While I was out of town with my family he spent days building book shelves from the floor to the ceiling, seven levels high, in my living room. He then filled the shelves will all the books. He told me that he would meet me at my apartment when I arrived home from my trip. He had me close my eyes as he walked me into my living room filled with flowers and candles. Then he told me that he knew that I have a lot of dreams and promised me he would help me achieve them, starting with this one. I love how his happiness is defined by helping me achieve my dreams.




Courtney: My engagement story isn’t a super romantic one of walks on the beach or as creative as the guy who organizes a flash mob, but my engagement was perfect, because it was so ‘us.’ We met in the summer when days are long, drinks are cold, and nothing is more fun than cruising around the countryside in a Jeep! (Midwest thing maybe?) It was only fitting that our engagement involved just that, as we met on a ‘jeep ride’. He had planned on proposing the weekend before but I was being stubborn and didn’t want to go! Being the patient guy he is, he made me promise we would go the next weekend. Looking back now, I can’t believe I did that!  So, as promised, we drove around on a beautiful day and our final stop was a amazing old barn that I have always wanted to go and look for treasures in. We went inside to investigate and little did I know that he has planned for this by setting up a tiny room of this barn with his great grandmas vintage school desk! We walked into this tiny room with only a desk and in my heart, I knew. He asked me if anything was inside of it, I walked over and opened it up. The most beautiful rose gold peach sapphire smiled back at me! I instantly burst into tears and he was down on one knee. I still can’t believe to this day that I am lucky enough to marry this guy.




Lauren: He told me he was taking me for a sailing lesson, but when we showed up, he had rented the same 40ft sailboat we took out with our friends on one of our first dates. We boarded and motored out to the bay and he told me to take over the helm so that he could put up the mainsail. We had music playing, and he changed it to ‘our’ playlist and joked that putting up the mainsail is very romantic. As the sail went up, pink and red rose petals started swirling back over me and out onto the water. At this point, I knew something was up, and he then asked me to look up at the sail and make sure it was all the way up. When I did, I saw that there was another sheet attached to it that said, ‘Will you marry me, Lauren?’ I started crying and he got down on one knee and proposed. I found out later that his uncle had worked on the sheet for weeks and then mailed it to the marina where they attached it and rolled up the sail with all of the rose petals inside. Everyone on both sides of our family knew he was going to propose but I was completely surprised. It was everything I could have ever imagined a perfect proposal would be.




Gail: We were stopped in Puntarenas, Cost Rica and were taught the meaning of the term Pura Vida, which translates in English to “pure life.” Costa Ricans use Pura Vida as a way of living, life is simple, short, and it is important to live it to its full extent.  While visiting Puntarenas we explored a Pura Vida Garden and decided to walk towards a small white chapel. My fiancé told me that he had a surprise for me, and asked me to close me eyes and open my hand. He put the ring in my hand and told me to open my eyes, then asked, ‘Will you marry me?’ Pura Vida.


Jaime: My fiance tricked me into thinking he forgot his wallet at my house! When I went downstairs in the early morning to check, I found two dozen roses, a caramel macchiato, and instructions to a scavenger hunt that would ultimately lead me to one of our favorite places, downtown Kirkland. He was waiting for me on a hidden pathway overlooking the water and it was there he popped the question!


You’ve seen our favorites – now it’s your turn to dazzle us with your ring and make us fall in love with your story! Enter here.