5 Real Engagement Proposal Stories

Tissues at the ready ladies and gents because here are the top five most romantic and sentimental marriage proposals that we have ever seen! A lot of thought, imagination, gusto and of course, love, is needed to follow these footsteps!

It’s something that you have probably been thinking about for some time, thinking about many different situations and responses in your head!


Your marriage proposal will be a tale that is re-told over and over again, so it needs to be somewhat good and one that will be cherished forever by your other half.

1. A Shock Proposal… and Wedding Day!

James asked Amanda to marry him during the Christmas holidays. Of course she said ‘I do’ but she never thought that she would be repeating it so soon in her surprise wedding four days later!

Their amazing photographer and friend, Jamie Delaine explains the story:

I got a call from Amanda’s mother the day before asking if I was up for the challenge of shooting a surprise wedding of one of my old friends. Umm, yep! Sure was. So, James and Amanda had talked in the past about eloping — so marriage quite quickly after engagement wasn’t something that intimidated them. James had this brilliant idea of getting married on Christmas Eve afternoon, with only Amanda’s immediate family present — and keeping it a surprise from his bride the whole time. Amanda and James were told by Amanda’s mom that she had booked an engagement session with me on Christmas Eve day for a gift… 

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Ok, let’s cut to the chase! Their photographer Jamie “suggested” they take the images near the church that James wanted them to get married in. Now, back to Jamie:

Amanda’s brother (who was also there for the shoot) said he’d love one of just the two of them so James decides to go inside the chapel. When Amanda walks into the chapel, James is standing at the end of the aisle, with an officiate standing right beside him. Amanda’s family is seated and her brother hands Amanda a bouquet, and the music starts, and down the aisle they walk.

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This proposal/ engagement/ wedding brings a little tear to our eye and a lump to our throats. For more, read Jamie Delaine’s Blog.

2. A Photo Booth Proposal

A. Pete wanted to propose to his girlfriend Shannon in a unique way, so what better way to do that than go to a Mexican restaurant spell out his his proposal in a photo booth!? Pete only had the exact change for five strips, so he was a little worried that he was going to jumble up the order of the letters, which explains his ‘Oh my god, I hope I got this right’ face in the last image.

Pete then stuck the photo booth images on their fridge and Shannon saw it when they were making dinner together! And they say romance is dead, we think not!

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B. When Kaylen told Pete of how much she loved the idea of getting engaged in a photo booth he decided to store the conversation away until a time when he needed it most. So, when the time was right, Pete organised a night out in the City Museum with all their friends. He brought Kaylen straight up to the photo booth on the third floor. Pete said they smiled for the first picture and then for the second he said “I have a question, Kay. Will you marry me?” He then pulled out the ring! She then smiled and, after some time, she agreed.

They then went back to the museum and hung out with their friends for the rest of the evening and had loads of gelato! Seen on Glamour.com.

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Oh how we love photo booths! It really is such a perfect idea to catch the proposal all on camera so when you are telling everyone about it, you can also show them as well!

3. Comic Book

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Wow, we just love this one! It’s so considerate and took the longest time to do! Australian illustrator Guy Shield decided to draw up a comic strip to propose to his girlfriend Liz. At first the comic appears to be a series of random pictures but when folded up it cleverly spells out “Will you marry me?”

Guy worked on it for months before finally popping the question during a trip to Bali.

Guy shares the rest of the story on his blog, Turn Olympus to Atlantis! What a guy, eh?!

4. A Cinematic Marriage Proposal

When Matt decides to play a practical joke his girlfriend Ginny, he decides to surprise her with an odd movie trailer in a cinema. The video explains itself. It’s definitely worth a watch!

Click here to watch the video on You Tube.

5. A Rooftop Dinner in New York City

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Kevin wanted to ask Stefanie to marry him in an elaborate and over-the-top display of his emotion. Why not?! To make it perfect, he wanted to propose to her on a rooftop in New York City on the night of her birthday. He didn’t want it to be a terrace. It had to be a rooftop with 360-degree views of the city. He also wanted to have a full dinner on the rooftop even though rain was forecast. On top of this, he wanted a large clear tent, a photographer, a horse carriage and loads for flowers and decor! As with all stories with a horse and carriage, Kevin had a very happy ending, pity the rain didn’t stay off! See Sean Gallery Photography and Style me Pretty for more on this proposal.

Find more great ideas on our Inspiration pages!

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