Personal Proposal Tips

One of the most popular requests we get is how to create a personalized proposal that has a big wow factor but isn’t cliche or cheesy. A surefire way to accomplish this goal is to really think about your sweetheart and your relationship. To include those special touches that you know they will love! Here are some thoughts on how to make your proposal more personal.

Personal Proposal Tips


Take a walk down memory lane with your favorite photos throughout your relationship. Or, send us a sweet collage in a memento box for her to “find” right before you pop the question.

Haiku Mill proposal

Maui proposal made personal with photos

Haiku Mill proposal with photo aisle

Victor decided to paint scenes of meaningful milestones in their relationship to display along the path to the gazebo where he proposed to Mariah.

Victor painted canvases to display leading to the Maui proposal

Mariah seeing personalized paintings right before Maui proposal

Maui gazebo proposal

Incorporate “your song” for a personal proposal

If you have a special song together, hearing it sets the tone for the romance.

For Jack’s proposal to Christine, we planned for a ukulele player to learn their special song. Said ukulele player also “just so happened” to be playing it as he passed by them on the beach. (Wink wink!) After the proposal, the musician treated them to a mini private concert. Romantic, right?

Ukulele musician plays couple's favorite song before Maui proposal

Maui beach proposal in flower circle

Private ukulele concert after Maui proposal

Incorporate keepsakes or inside jokes

When Blake met Kristina, she was working at a bakery. He came in to buy chocolate-covered strawberries. She was holding hot dog buns and he said, “Hey, nice buns. How much are your chocolate covered strawberries?” To pay tribute to the way they met and also their shared love of pirates, Blake sent us a treasure chest to bury on the beach. Can you guess what it was filled with? Yep, hot dog buns and chocolate-covered strawberries.

This was a super cute idea that fit into Kristina and Blake’s story. We have had some guys inquire about doing a treasure chest or other ideas they have seen online without any connection to their relationship. The key here is to think of something that makes perfect sense for your love story!

Buried treasure proposal on Maui

Beach proposal on Maui

Meaningful ring holder

We normally tell you not to keep the engagement ring in the box and put it in your pocket instead. This is because the bulky outline is pretty recognizable and will give away even the stealthiest planners. However, in some cases, it makes sense for the ring holder not to be a box at all but something else entirely.

Chris and Jamie met at a bar. Jamie had just come from a wedding and was a little tipsy. Long story short, she showed Chris a cactus she received as a gift from the wedding, told him to take her on a date to get sushi, and put her number in his phone. When Chris texted her the next day, she didn’t remember him but ultimately decided to give him a chance and was very impressed that he took her to one of the best sushi restaurants in Houston.

For the proposal, Chris created a scrapbook of their favorite pictures and memories such as a menu from their first date. He ended with a small cactus. Since Jamie actually lost the cactus from the night they met, he said he found it and something special had grown in it over time. Then, he presented the ring and asked Jamie to marry him.

Proposal in south Maui

Cactus engagement ring holder

Personal Maui proposal

For Antonio’s proposal to Harry Potter fan Daniela, he sent us the Golden Snitch which had a copy of the Unbreakable Vow page inside. Our photographer set up the Golden Snitch for the couple to find right before the proposal.

Golden Snitch engagement ring holder

Couple finds Golden Snitch before Maui proposal

Maui cliffside proposal

Involve loved ones

If your sweetie is super close to family and friends, she will love knowing that they were involved in the proposal from asking for her parents’ blessing to getting sisters or best friends’ input on the perfect engagement ring.

We’ve planned many proposals that involve double surprises, with the engagement being the first surprise and having loved ones join in on the photo shoot later or be there at dinner as the second surprise. The look of shock and awe when she sees her nearest and dearest there is priceless!

Family surprise after proposal

Family surprise after Maui proposal

Family surprise after Maui proposal

Beach proposal in Maui

Maui engagement photography

Friends surprise at dinner after Maui proposal

Friends surprise at dinner after Maui proposal

When loved ones can’t be there in person, that’s when technology comes in handy. For Mikey’s proposal to Caitlin, he actually called her mom right before the proposal and put his phone back in his pocket so she could hear the whole thing.

Looking at new engagement ring

Maui proposal on North Shore

We’ve also had several ladies FaceTime their besties to tell them the great news right away, and we’re able to capture that special moment too!

Maui beach proposal with birds

Facetime moment after Maui proposal

Ready to Plan Your Personal Proposal?

We can’t wait to hear your love story and help you brainstorm a personal Maui proposal true to your relationship! Contact us today to get the planning started!

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