Best Proposals

Maui Wedding Proposals

Wedding Proposals

Here we’ve compiled some of our favorite wedding proposals, some past clients, some friends, and some urban legend. We hope these Proposal ideas are helpful to any one looking for a unique way to pop the question. It doesn’t have to take a lot of money, romance and imagination is much more important.

If you have a great proposal story please E-mail it to us, we would be happy to post it on our site.

Story Book Proposal
"He took me out to dinner, and afterward we went to Barnes & Noble. We meandered over to the children's books section to pick up a few Christmas presents, and then he pulled a little red book off the shelf and said, ‘Oh look, what's this?' The book was called, Fun with Emily and Jarrod, kind of like a Dick and Jane book, but instead, it was the illustrated story of our relationship. He read it to me, and at the end, the ‘Jarrod' in the book had a pressing question to ask the ‘Emily'...and he pulled out the ring and proposed! The last page of the book said, ‘The beginning...'"

A Real Winner
"The date of a triathlon I was competing in happened to fall on the two-year anniversary of the night I met my fiance. After a 1-mile swim, a 24.2-mile bike ride, and a grueling 6.2-mile run in the hottest part of the day, I rounded the corner and headed for the finish line. My friends and family were cheering as I crossed it, but then I received the biggest surprise of all! Right at the finish, Brian was down on one knee holding my finisher's medal and a ring!"

"My sister, who was in NYC doing an internship at US Weekly magazine, asked if she could take pictures of me holding the magazine for a project she was working on. When I got to the "Shopping" page, I noticed a picture of a really cute dog in an ad. I thought, ‘He looks just like my dog, Aspen.' Then I realized that it was my dog -- and he had an engagement ring. The ad included my name in big letters, and read, "Will you marry me?" Then my fiance came out of nowhere, got down on one knee, and proposed. For the next week, I continued to get emails and calls from people that knew me and had seen the ad in the magazine. It was amazing!"
-- GingerAsh925

Artfully Done
"We were at the museum, and in the middle of one of the exhibits was a timeline about scientific discoveries and advancements. At the end was a slideshow of pictures of us and our families that he'd had the museum add. It read: 'On February 16th, 2008, Will discovers that he is a perfect match with Andrea.' As soon as I saw it, he got down on one knee and presented me with an engagement ring."

The Right Words
"He took me to a local rose garden to play Scrabble. It was a travel Scrabble board where the letters stick in place, so when I opened the board and saw letters already in place, I thought, I don't think we were in the middle of a game. I took a second look, and saw that he had spelled, "Laura, will you marry me?" When I looked up at him, he was on his knee holding out the ring. We haven't taken the letters off of that board since."
-- lmburi

4th of july proposal.
My fiance and I were off to our annual family 4th of July picnic. Very normal day, lounged around till the party started. Get to the party, chatted a bit with family then my aunt called attention to everyone to gather around. She had said that her three children had prepared a cheer about the family and that they wanted to sing it for everyone. Everyone was all excited, we sat and waited for the kids to come out and start. They began with pom poms and all saying ”2,4,6,8 Mark and Jess are really great”
After that first line i was so excited that they had put me and my fiance first in thier little song. They continue…”8,6,4,2 We think Mark should Marry YOU!” Me, still CLUELESS, thinking, O my i cant believe that they would put that in the song, considering people harass us about getting married all the time. After they said that line all three children turned around and on the back of their shirts it said ”Will you marry Mark?” I looked at them and then i look at Mark (my fiance) and he got down on one knee and said that he wanted to spend the rest of his life with me and i just about fell over!! I was in TOTAL shock and could not move for about an hour after that. MY whole family was there to see what a sweet job he did, and he involved the three most important children to me as well!! It was absolutely perfect and I feel that nothing can top that, especially the look on my face when it happened!!

The video of this whole event is on entitled \”Jess and Mark engagement\” Go on and see for yourself that it is the BEST!!
Jessica Pittman (Pittsburgh, PA)

Umbrella Marriage Proposal
Well, it all started with a dream.

I woke up one summer Sunday morning (June 8, 2008) and looked over at my girlfriend with the biggest smile on my face. I told her, “I know how I am going to propose to you!”

She proceeded to say: “Don’t tell me, don’t tell me.”

I wasn’t going to by any means; I love surprises.

My dream consisted of a bunch of umbrellas lined up in row with each umbrella having a different letter on it to spell out the words “WILL YOU MARRY ME?”
The next step was to figure out when I should propose and without even second guessing myself I decided to do it on June 20, 2008. Knowing that my fiancée, Betsey, had two of her closest friends in town from Florida and California that weekend would make this experience even more memorable.

Swept Off FeetI now had 12 days to plan the surprise. The first few days consisted of picking out the engagement ring; thanks to the sales consultant who had already been talking with Betsey and her mother made it a little easier and much quicker than I anticipated it would be. So I picked it out, came back a week later to pay for it and to pick up this gorgeous, platinum engagement ring.

Now, having the idea, the date, the ring, it was time to ask the future in-laws for their permission to marry their beautiful daughter. Without any hesitation I went over to their house, bringing a bouquet of flowers for my future mother in law (which doesn’t hurt the situation one bit!) We stepped out to the porch, beers in hand, and I said, “As you know I love your daughter very much and I couldn’t be happier in life than I am with her. I am here today to ask for your blessing to marry your daughter.” Without any hesitation and a few tears (happy tears of course) I had their blessing. As soon as I had their blessing I pulled out a detailed plan of how everything is going to happen for the next few days.

Monday, June 16th – Ordered 30 black umbrellas to be delivered on the 18th.

Tuesday, June 17th – Asked parents for their blessing.

Wednesday, June 18th – Painted the top of each umbrella at a friend’s house to spell out “WILL YOU MARRY ME?”

Thursday, June 19th – Made sure everyone who was involved was very well informed on what was going to happen Friday evening.

Friday, June 20th – The proposal

On Tuesday night, I sent out a blast email to all of my close friends, family and to all of Betsey’s close friends and family to let them in on the surprise. I told them where it was going to happen (Lake Calhoun); what time to meet at Betsey’s parent’s house (7:00pm) and how each of them would be involved. Different people had different duties. There was a group of people who were in charge of getting everyone to the location on time and to practice the proposal. There was a group of people who went incognito and followed around the lake with a video camera. And then there was the group that walked around the lake with Betsey and me.

On Wednesday after watching the FedEx tracking online and knowing the package of umbrellas were delivered I proceeded to head over to my friend’s house. There, the three of us started to spray-paint letters on the top of each umbrella.

The Big Day… I had to convince Betsey that I really wanted to take a “walk” around Lake Calhoun on Friday night say around 6:15pm. Not an easy task, but with the help of her best friend, Molly, flying into town with her boyfriend from Florida made it a little easier to persuade her.

I made dinner reservations at a local restaurant around 8pm so that the four of us would have enough time to have a drink and to walk around the lake. The dinner reservations were a nice decoy. With Molly and Tom arriving at our condo, I told Betsey that we really needed to do this walk because it was a long day at work for me and I needed some fresh air. So we drove over to Betsey’s parent’s house, who actually live a block away from Lake Calhoun. We went inside and chatted for a bit and finally got on our way with the big walk.

Unexpectedly the surprise was almost blown by an early arrival… luckily Betsey’s dad took care of that situation without any of us knowing.

With my hands in my pockets feeling the ring every two seconds made this walk a little nerve-wracking. I also kept looking around trying to find my incognito friends who were on the 007 spy mission filming the walk and not once could I see them. Upon the finish of this three mile walk around the lake we proceeded to walk towards this line of people all holding an umbrella right above their heads.

Betsey was very intrigued on what was going on and wanted to take a closer look so we all played along. About 100 feet away, someone counts 1-2-3 and everyone flips their umbrella over to spell out the infamous “WILL YOU MARRY ME?”

Betsey starts looking around saying, “Oh my gosh, someone is getting engaged!”

I smiled and got down on one knee and slipped the ring on her finger while saying:

“You know I love you with all my heart and there is no one else I would rather spend the rest of my life with than you… will you marry me?”

With her hand over her heart she said yes!

As if the proposal wasn’t surprise enough, the crowd of umbrella holders started to walk toward Betsey and even more shock was brought to her face. The crowd of umbrella holders started to get familiar to Betsey as they got closer… her mom, dad, brother, cousins, aunt, uncle, close friends and my dad, mom, step-mom, brother, sister-in-law, niece, and close friends were all here to witness a beautiful moment. And a special moment it was since Betsey was so surprised!

After the proposal we all went back to Betsey’s parent’s house for a champagne toast followed by drinks and apps at a local drinking establishment.

Sean Palmgren
Minneapolis, Minnesota

Six months salary diamond engagement ring
I didn’t have a lot of money so it took me 6 months to pay for the ring. This worked out well as it gave me time to discover a really nice restaurant and plan the event. I got the manager at the restaurant to work with me to make the plan just right. Early in the day, shortly after the restaurant opened, I dropped by the restaurant with a really nice flower arrangement and the ring. I asked the manager to make sure we had a semi-private area of the restaurant and next to a fireplace. I also asked the manager to put the flowers on the table and bring out the ring with the desert menu. He stored the ring in the safe until it was time.

When my fiancé and I arrived at the restaurant, we were taken to a great table tucked away in the corner of the restaurant and were seated. After some wine and some great food, it was time for desert. The desert menu arrived with the ring; I went down on one knee, took the ring box off of the menu and asked her to honor me by being my wife.

It was one of the greatest nights of my life and we are now happily married with two great kids.

- Jason L., Lower Sackville, Nova Scotia

Beach WeddingCoffee Shop Marriage Proposal Story
The first time I ever saw her she was sitting in a coffee shop at my brother’s college 3 1/2 hours away from where I lived. My brother knew her and introduced me near the end of the night. As he and I were leaving I told him she was cute and he should be nice to her. Fast forward 14 months and I knew that she was the one for me. I picked out her ring myself so she had no idea it was coming. I drove the 3 1/2 hours on a Thursday afternoon; I had a dozen roses, 12 cards and a spool of twine. Her roommates were keeping her distracted while I set everything up. The first six roses were scattered around campus at all of the different places that were important to the development of our relationship. Each rose had a card with a poem that hinted to the next location. The last of the six led her to the coffee shop where we first met. The last 1/2 dozen roses were in a vase on a table and the card told her to order some tea for the both of us and imagine being on a date with her amazing boyfriend. What she couldn’t see was that I was hiding behind the counter, where I had been crouched for the last 40 minutes waiting for her to arrive. When the tea was ready, the man handed it to me and I carried it out to her. I set both cups on the table, got down on one knee, unfolded the napkins to expose the ring and then asked her to marry me. I had arranged for her closest friends and my brother to be waiting for us at her apartment when we got back. I also knew that she loves dessert pizza so I had three of them delivered. She got to spend time alone with me and then show off her ring and tell the story to all of her friends at the same time.

- Ehren W., Des Moines, Iowa

Restaurant marriage proposal with details
Where do I start? Well, I’ll start with the whole dinner plan. Before Dan even got here, probably about 3 weeks or so before he was going to come, I had made an itinerary of everything that we would be doing while he was here. Going out to Livingstone’s for dinner was on that list. Everywhere we have been we have tried to have at least one date night where we dress up and go to a nice restaurant.

Well, about 2 weeks before he was going to come he sent me a picture of a ring in an e-mail. This is what he said, “Don’t worry, I’m not saying anything by this but just saw this ring come up on yahoo and it made me curious to your style. Do you like this type of ring or what is something that you would look for in a ring? Send examples if you want, or whatever.”

I knew that it was going to come up sometime soon, but he told me that we should probably go ring shopping in the states when we are together. So I didn’t really think he was going to ask me when he was here… PLUS, it takes such a long time for something to get to Dakar, and he’s not exactly the type of person to send something express mail. So I didn’t think he was going to buy the one that we both really liked.

Anyway, back to dinner. So when Dan and I were all ready to go to dinner, I ask my dad to get a picture of us. He pulls out his camera and takes a couple of pictures (which I thought was a little weird at first… I had Dan’s camera in my hand, I thought he was going to use Dan’s), but I brushed it off my shoulder. Then my mom and little sister came out into the living room too, and just were smiling, and staring at me, which now that I think about it made it seem a little weird at the time…

So we left, and got to the restaurant took a seat next to the door (the only other option was by the window at a 4 person table with other people around) I didn’t really like it because sometimes they seat people at the same table if it’s meant for 4 people.

So we go and sit down and he’s sort of jittery. He’s like, “I have to go to the bathroom”. So he goes to the bathroom and comes back a good 5 min later. We sit down order a bottle of Chardonnay, and he was like, “These are really nice glasses. (Points to the glasses on the table [they are tall wine glasses that say Livingstone’s on them]) I wonder if the waiter would let us keep them.” I was thinking to myself “Oh, my gosh… He’s going to do it tonight isn’t he?” And so I got myself all worked up, and I was all excited, and then Dan was like, “Well, the reason for that is because our two year anniversary is in May, and since we won’t be together for it, this dinner can be our make-shift anniversary dinner.” (What a good excuse, let me tell you, Dan is really good at thinking things up off the top of his head!) So I was really excited and had butterflies in my stomach, but then I was let down when he said that…

So the waiter comes over and pours our chardonnay, and we order food. And During the course of the meal we start talking about our past together, and about our future. And all these other things that made the meal really romantic. Then he was like, “Man, I have to go to the bathroom again.” And I was like okay… I might have to go a little too, so I got up and went to the bathroom.

(What I didn’t know then was that he was trying to get me to go to the bathroom so that he could grab the box with the ring in it out of his jacket pocket to put it in his lap.)

So we get our dessert, and it looks really nice, we have the waiter take a picture. And then we start talking again, he say’s something like “I really want to be with you forever, baby” and I was like, “Well, you’re just going to have to ask me to know what I think…;)“ and he was like, “Soon sweetheart, soon.” And then he was like, “but if I ask you, that means I’m going to have to ask your dad for his blessing. Do you know how scary that is?
“That’s not scary sweetheart.” And I tell him a nice long speech, well what I would say if I was him.
“Yeah, like I’d be able to say all that. Your dad is intimidating. I’ll do it over the phone later”
“Well, I was sort of hoping that you had already asked my dad, and you were going to propose to me tonight”
“Baby, now, how would I get a ring so fast? I haven’t asked your dad yet, he’s going to say no because you haven’t finished your degree yet”

(SO, I had gotten my hopes up once again, thinking to myself, “Well maybe, just maybe, he had already asked my dad and will propose to me”… but then I was let down once again)

We finish our dessert, and he asks for another glass of chardonnay (we had already finished our whole bottle). The waiter pours us our wine, and then Dan starts out saying,

“You know sweetheart, I’m really glad I found you. You really are my best friend. You know, I never knew what other people meant when they said that they married their best friend, but now I know because you really are. We are so perfect for each other. You’re my soul mate. You are everything that I would want in a wife, a mother (in time), just everything that I need. (He stands up and starts to walk over to me… I was thinking that he had to go to the bathroom again) And because of those reasons, that’s why I’m getting down on one knee (he gets down) to ask you to be my wife. I love you Amanda, you mean so much to me, and I want to share my life with you. Will you marry me?”

Of course, I started crying when he was talking about how I was his best friend, so I started crying even more when he got down on one knee, I think I was in shock when he did it because I remember saying “Oh, my gosh”, out loud.

I said, “Yes, of course I will. I love you!” and we kiss and hold each other there for like 5 min, crying my eyes out because I was so happy. Then he puts the ring on my finger. And it’s so pretty!

- Amanda S., Kingsport, Tennessee

Akia Weddings & Events, Maui Hawaii Wedding Planners
PO Box 2099 Kihei, 96753
Phone: 808.870.5525



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