The Woodland Events Blog

  • Todd Harper

7 Proposal Stories that Make Us Go "Awe"

Updated: May 12, 2020

One of the first questions I like to ask couples when I start planning their wedding with them is, "So, how did you propose?" There's something about proposal stories that just make my heart go "awe".

From simple stories like, "We were in a beautiful garden together and the time was right. I didn't have a ring yet, I didn't have the right words, but I decided to get down on one knee and ask her to be my wife," to elaborate stories that involve jumping out of a plane together from thousands of feet in the sky, I'm always so excited to hear the unique ways "in a relationship" became "engaged".

With engagement season starting this month, I'm writing about some unique proposal stories I've heard. Some of these stories will reveal how two people fell in love. Some will share the promise of a life of togetherness. Some might make you laugh while others make you ugly cry. All of them will tell of incredibly unique relationships between two people.

Before we get started on sharing those stories though, I'd love to offer some quick insights into planning a proposal that's perfect for you and your soon to be fiance.

  • Make it personal and unique for you. Incorporate inside jokes, shared hobbies, and important people and places. This will help make it a story worth telling for years to come and stand out among the thousands of other proposals happening every day.

  • Get other people to help. You may want to have a photographer, videographer, chef, servers, or more. These can be hired professionals or friends and family who are willing to help out. Just be careful who you tell which details to and only share what people need to know for their role in your proposal. The more people who know and the closer they are to you and your partner, the more likely it is that someone accidentally spills the beans before you pop the question. Secrets are hard, you know?

  • Consider your partner's level of extroversion/introversion. If they don't want to be seen getting proposed to in front of 1,000 people, don't propose in front of 1,000 people. You may have a partner who's more interested in a cozy candle lit dinner at home than in the middle of Times Square.

  • Rent space and/or get permits. If you do choose to plan something elaborate in a public space, be sure you make all the legal preparations so you don't get in trouble. While it might make a fun story in a few years that you got arrested for proposing to your partner, it might kind of kill the vibe in the moment. Each city and county has different permitting requirements, so check out their websites and see what you need to get (photography, obstruction, and noise permits are the most common). Also, if you'll be on someone else's property, be sure you have their permission to be there (or even a rental agreement).

  • Use diversion. Make them look left, then go right. Just like a magician uses diversion to awe and surprise an audience, if your partner doesn't see the proposal coming, it will make the moment you pop the question that much more exciting! You can take this literally, like saying, "Wow, look at that sunset," and taking a knee behind them while they look. You could also do something more subtle, like slipping "marry me" into an otherwise casual conversation. However you use it, a little diversion will go a long way.

  • Put timing into context. If your partner is generally feeling angry or tired after a day at work, that isn't the best time to plan to ask them to marry you. Do it at a time when you know they'll be feeling relaxed, easy, and ready to answer a question that's going to impact the rest of their life (and yours).

  • Do it the way they want you to do it. They may have told you explicitly or perhaps you just know them well enough to know. If they aren't in to fancy dinners, don't go to a fancy dinner. If they're not in to baseball, don't do in at the Jumbotron at your favorite team's game. Be sure you ask the question in a way they would want you to ask it.

  • Don't eat the ring, drop it in water, or have your pet carry it. I've heard of many proposal stories (not written below) where the very expensive ring was lost because it was dropped into the ocean off a kayak, tied poorly to a dog's collar and fell off in the middle of a hike, or it was consumed after being baked in to a cake. Murphy's Law of Engagement Rings says if you can lose it, you will, so when planning your proposal, think of all the ways you could potentially lose the ring and find alternative solutions.

  • Keep it a secret for a minute. Just after your proposal, enjoy having this moment together as a newly engaged couple. Keep it your special secret for at least a few moments. Then, be sure you call your immediate families and let them know the good news before blasting social media with your new relationship status.

  • Plan it out meticulously and then forget the plan. It may sound odd for a professional planner to tell you to forget the plan, but it's true. Go with the flow and stay in the moment. If you have an elaborate proposal plan but the perfect opportunity arises to ask the question early, do it! If you wanted a flash mob and only two people showed up, rock it like that was supposed to happen. At the end of the day, it's about two people celebrating their love for one another, not how many backup dancers you had (psst: the same is true for the wedding).

  • Hire us to help. We love proposals so much that we offer to help you plan yours for the very low cost of $75. We'll help you think of an idea and set it in to action. We'll acquire permits for you, help you shop for a ring, recommend and hire any professionals you need, and stay behind the scenes during your proposal to make sure it happens the way you want it to. Then, if you choose to use any of our wedding planning or management packages, your full proposal planning fee is applied to the wedding planning fee.

Alright, now that we've gotten through all that, let's look at those amazing proposal stories!

1. Coffeeshop Storybook Proposal

Because I'm pretty biased, I'll start off with my own proposal story. Actually, it's fitting that I'm writing this today, because it was exactly 3 years ago this morning that I proposed to my wife!

For context, long before we started dating, I got to know my wife by spending Sunday mornings with her and another friend at a coffee shop before church. One time, I brought in a copy of Hyberbole and a Half to read a few entries for giggles. Somehow, this evolved into reading children's picture books to each other every Sunday morning, a tradition we carried on weekly for several years.

Fast forward to when the time came to propose, I knew there was only one way I could do it: to write a custom children's book about us and read it at Sunday morning story time. So I hired a children's book author and an illustrator to help make this a reality. The book had to be about a red panda (me) and a brown bear (Claire). It had to have several vignettes about our experiences together throughout the book without being so obvious that Claire would figure out that it's about us before the surprise ending. And it absolutely had to rhyme, since that's Claire's favorite kind of children's book.

Once the book was written, illustrated, printed, and bound, I gathered with our usual coffee/story crew (which had grown from three people to five) and read this really great, professionally written story book about us out loud on a Sunday morning at Zizzo's Coffee in Santa Barbara, CA, surrounded by friends, strangers, and baristas (who were in on it and helped film and photograph the occasion).

After ending the reading with "Claire Bear, will you marry me," Claire started crying and kissed me. She never technically got to the part where she said yes, but we're married now, so I guess that was supposed to be implied.

2. A Proposal Hidden in Plain Sight

Self-proclaimed spontaneous improviser Edi Okoro decided he'd propose to his girlfriend Cally by taking the ring with him everywhere they went and taking photos of it right in front of her. Okay, sometimes behind her too. He figured he'd either propose when he found the perfect moment to do so or until he got caught.

Whether she was holding the ring while taking a nap, focusing on something far in the distance through binoculars while the ring was placed right by her face, or passing by the ring when it was mixed in with her unsorted jewelry plate, she spent about a month with her engagement ring before she ever knew it was there.

The couple has yet to reveal how the actual proposal went down (we do know he never got caught and Cally didn't even know about the photos for several weeks after saying "yes"), but this is already enough of a story on its own, don't you think??

You can view the full album of photos he took in this facebook album.

3. Netflix and Propose?

In this modern world, it seems like Netflix is our new international pastime.

One man decided to take advantage of that and partnered up with Netflix to propose to his girlfriend Kamela. He created an elaborate scheme to surprise her as he made a guest appearance on a couch with the stars of Netflix's Santa Clarita Diet in a special short mockumentary titled "Keeping Love Alive" (it's actually available on Netflix right now if you want to go check it sure to watch it to the very end).

If you want to see Kamela's reaction, head to Twitter.

4. New Years Resolution

Anthony's girlfriend Jenny was obsessed with all things Disney. So it was only natural that he would propose to her in front of the castle at Disneyland. He brought his entire family and hers to Disneyland one New Year's Eve (to make things a little less suspicious).

At one point in the day, Anthony stopped the group in front of the castle, and asked, "Hold on everyone, why are we all here today?" Their families, who were in on the secret, paused for a moment of awkward silence and holding their breath as if to ask, "Do you actually want us to tell you we're here to see you get engaged?" Of course, nobody wanted to volunteer that, so they just continued the awkward silence until Anthony chimed in with, "For New Year's Eve, right??" Around the circle, there was a deep sigh and exclamations like, "Oh yah," "Of course," and "Mmhmm...that's what I was going to say!" Anthony continued, "I thought we should all go around and share our new years resolutions."

So they went around the circle, each person sharing what they were going to achieve, or give up, or try to do better this year. When it got back around the circle to Anthony, he turned to Jenny and got down on one knee as he said, "My resolution make you my wife."

And he succeeded! The following November, they were married!

5. A "Traditional" Proposal

Family traditions play a big role in our lives, and sometimes, in our proposals.

Brad's family had rather an unusual tradition. For as many generations as anybody knew, every single member of their family had gotten engaged in a bathroom, surrounded by other members of the family. Of course, there's always the question of how you get the two partners in a bathroom together with other members of the family without arousing suspicion.

When Brad and his girlfriend Emily were visiting his parents' house one Thanksgiving, Brad didn't feel so great after dinner. He went to lay down in bed for a bit while his mother and Emily tended to him. Soon enough, he rushed to the restroom with no time to close the door. He kneeled over the toilet (curiously, only on one knee), and started relieving himself of the giant turkey dinner (or so everyone thought).

Members of Brad's family quickly made their way to him to see if he was alright. All were surprised to find that the toilet was completely clean and Brad had a giant grin on his face. His mom, aware of the tradition, gasped and exclaimed, "It's happening!!!" Emily, who had not been made aware of this particular family history wondered what "it" was.

Brad, still on one knee, said, "Emily, will you marry me?" Her response: "What? Here?!? No, but you can ask me again in the hallway." So he did, and she said yes.

I think the real question here is whether their children will continue the bathroom tradition. Or perhaps they'll always do a bathroom-adjacent hallway.

6. Have I Got a Day Planned For You

I love a good scavenger hunt. Especially one that ends in a ring!

Christy woke up one morning to find that the phone on her nightstand had been replaced with a handwritten note from her girlfriend Erica. The note read, "Hey lovely! Have I got a day planned for you! Hurry up and get dressed and meet me at Mugs [the coffee shop on the bottom floor of their apartment building]! See you soon!!" Christy was both excited and low key annoyed about this.

She obliged and headed down to the coffee shop, where Erica was in fact not waiting, but several baristas who were close friends of theirs had her favorite coffee order ready and a message to head to a nearby diner (which happened to have her favorite breakfast food in town). She was greeted at the diner not by Erica, but by a table full of the ladies' best friends. They invited her to sit down for a while as they each shared their favorite memories of Erica and Christy. They sent her along to the next stop, which sent her to the next, and so on. At each stop, Christy found surprise family, friends, and a few strangers who aided in getting her to the next point in this scavenger hunt. One stop even included two of her college roommates who she hadn't seen in several years and who lived in another state.

Eventually, she reached a stop where she finally got her phone back. It rang the moment she touched it. It was Erica. She said, "Just thought I'd give you a ring. I have an important question for you! Come to the bridge!" Across the street from the previous stop was a park the couple had walked through on their first date (and many times since).

When Christy arrived, Erica was waiting for her at the bridge and asked Christy to be her wife. When she said yes, many of the people who'd been at stops throughout the day suddenly appeared around them to celebrate.

7: Picking the Ring and Popping the Question

After his grandmother's ring (the one he was going to give Dakotah) was stolen, Josh took his girlfriend to a local jeweler to pick the perfect ring with her. When they arrived, there was a camera crew setting up on one side of the store and the manager said, "Sorry for the cameras, we're filming a commercial today. How can I help you?"

Josh and Dakotah browsed for a little while until she found a ring with a pear shaped diamond that she loved. The manager said, "Oh, how funny, this is actually the one we plan on featuring in our commercial today! And you're the star!"

The cameras immediately turned to the couple as Josh got on his knee right there in the jewelry store and asked Dakotah to marry him.


Have you got a fun proposal story you'd like to share? Send it to and we'll be sure to include it in a future proposal blog :)

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