11 Women Share Their Adorable, Tear-Jerking Proposal Stories

Toa Heftiba
Toa Heftiba


“It happened the day after my birthday, so I wasn’t expecting it at all. I came into work (it was a Friday) and he had decorated my entire office with balloons, streamers, and little Post-it notes with things he liked about me written all over them. On my desk was my favorite Peet’s coffee and a homemade chocolate muffin. And when I turned around, he was hiding behind the door in his best suit. I was instantly in tears.”

— Mallory, 28


“I’m a high school teacher, and at the time, my boyfriend and I lived only a few blocks from school. This particular day, he asked me to run home and check if the garage door was shut because he didn’t think he shut it on his way to work. In the time it took me to go home and back, he had gotten 15 or so of my students in on his plan. When I got to school, each of the students was holding a hand-written love note from him, which led me to different places around campus and then finally to the library, where he was sitting in a chair, holding the most beautiful ring I’ve ever seen and a giant heart-shaped balloon. Not only was I surprised, but the best part was that I got to share the moment with my students, which made everything even more special.”

— Jessica Ann, 32


“He proposed to me in the sky, in a hot air balloon. The magic of the moment honestly took my breath away. For a moment, I couldn’t even say ‘yes,’ I could only nod my head as tears poured down my face.”

— Raven, 45


“I was previously married young, and I have a little boy whom I love with all my heart. My boyfriend proposed to me via my son, who asked me if I’d want to do a puzzle with him on a Saturday morning when my boyfriend was supposed to be out golfing with his buddies. When my son opened the puzzle, it was pieces that created a picture of my boyfriend and I. And then my boyfriend came out from around the corner, holding a ring. Such a beautiful moment. I still get choked up thinking about it.”

— Alyssia, 32


“My boyfriend secretly flew my family in (they live across the country) to be there for the big moment. He did it at night, in the middle of the Maggie Daley skating rink under the stars and hands down, it was the most beautiful moment of my life.”

— Kimmie, 24


“My BF was supposed to be out of town on business, and all my girlfriends, even the cross-country ones, were supposed to be coming in for a huge girl’s weekend. Little did I know, he’d talked to them all, and planned this all in advance. We walked into the restaurant, and there he was, at a table in the center of the room, ring in hand.”

— Paige, 28


“We hadn’t been together for that long, but we were in our early thirties, and very serious about our relationship. He took me to a beautiful dinner in a restaurant that had a view of the entire city and asked me by reading me a three-page letter that he said he started writing the day we met. My heart was a puddle.”

— Joan, 51


“It wasn’t just how he asked, which was adorable, it was who he asked. Before actually popping the question, he asked permission from my parents, my siblings (all four of them), and my two best friends. He wanted them all to know how much he cared for me and it has made their relationships so much better than I could have ever imagined.”

— Lis, 29


“I’m a very religious person, and something that’s important to me is my faith in God. My boyfriend always honored me and my faith, but wasn’t actually a believer when we first started dating. I was planning on going to India for a two-week mission trip about six months into our relationship, and he proposed to me the day I left by surprising me at the airport with not only a beautiful ring, but with his bags. He decided to come with me! And now, three years later, he has become both a Christian and my wonderful husband and all I can say is, wow. I am so blessed.

— Lily, 31


“We went to a movie on a random Wednesday night. There wasn’t anything special about the day, which I think is why it was so amazing. Before the movie started, there’s all those commercials, and suddenly one pops up on the screen, ‘Henley, will you marry me?” and the house lights come on and my boyfriend gets down on one knee. Oh. My. Goodness. I was so surprised.”

— Henley, 25


“My younger sister has Down Syndrome, and she’s a huge part of my life. My boyfriend knew this, and somehow he got her in on the surprise. My sister and I were were coming home from dinner and the entire cul-de-sac on our street was decorated with candles. My boyfriend was standing there holding a bouquet of roses and my sister suddenly pulls the ring from her purse. It was so precious to me that he included her in my special moment. He’ll never know how much that meant to both me, and her.”

— Isabella, 34 Thought Catalog Logo Mark

About the author

Marisa Donnelly

Marisa is a writer, poet, & editor. She is the author of Somewhere On A Highway, a poetry collection on self-discovery, growth, love, loss and the challenges of becoming.

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