Woman shocked to see friends surprise her after proposal on Maui

While many couples prefer for their proposal to be a private moment, we’ve also seen an increase in those who want their families to be involved in their proposal plans. There are several ways to allow your nearest and dearest to be part of the next step in your relationship, whether they are here in person or celebrating you from afar.

There are so many ways to incorporate family into your proposal we split this topic into two parts. This first part will focus on a family proposal when they are here on Maui too.

If you want to involve loved ones in your Maui proposal but they won’t be able to travel, then part two is for you.

Since Maui is a vacation destination, you may be traveling here with family and using the trip as the perfect time to propose.

If they are on island with you and have the option to be at the proposal, you have to ask yourself the following questions:

– Do you want loved ones to watch the proposal?
– Or would you rather have that moment to yourselves and celebrate with them afterwards?
– Can family help you pull off a great cover story?
– Or do you think they will ruin the surprise?
– Do you want family to be part of your photo session?

Your answers to these questions will help us determine the best way for family to be involved, while still making sure you are happy with the plan. Your comfort in the proposal plan is key to its success!

If you want family to witness the proposal

If you want family to be able to watch the proposal take place, you can all come to the proposal spot together or family can arrive early to hide and watch the proposal in secret.

Family photo session cover story

When you arrive to the proposal location together, we often use the cover story that you are there for family photos. This gives you a reason to be dressed up for pictures and be at the proposal location at a specified time.

We also suggest you have your mom or their mom or whoever is planning your Maui vacation tell you and your future fiancé about the family photo shoot. That way, it seems like this photo shoot is not your idea and you are just going along with it.

The family photo session cover story works well if…
– you are not the planner in your relationship
– you would have a difficult time getting your sweetie to a certain place at a certain time without arousing suspicion
– you know they want to be dressed up
– family photos is something your family would appreciate (whether family photo shoots are a regular thing for you or your family is long overdue for photos)
– it would help you to have more direction from the photographer

In the family photo session proposal, we usually do spend the first portion doing family photos. When it’s time for couples photos, the photographer usually leaves you and your sweetie for last. Then it’s proposal time and the rest of the photo session will be focused on engagement photos.

Mona thought they were doing a photo session with her family until AJ got down on one knee.

Family photo session in Maui used as a cover story for proposal photography

Family photo session in Maui before surprise proposal

Photo of parents and son with his family

Mom and dad in the middle with son and daughter on one side and another son on the other side

Brothers with sister in the middle

Mona and AJ before proposal

AJ turning to Mona before getting down on one knee

Sequence of getting down on one knee at the beach on Maui

Proposing on the beach in Maui using family photo session as a cover story

Proposing on the beach in Maui using family photo session as a cover story

Putting engagement ring on

Reaction to proposal during family photo session

AJ celebrates after proposing

Mona reacts after getting engaged

Mona is all smiles after saying yes to AJ's proposal

Mona's mom hugs AJ after he proposes to Mona

Family hug Mona and AJ after engagement

Congratulations after Mona and AJ get engaged on Maui

Family celebration after AJ's proposal

AJ and Mona embrace and smile after surprise proposal

Mona and AJ kiss on the beach with naupaka and palm trees in the background

Jamin and Lyndsay’s group included her mom and stepdad, sister and family, as well as Jamin’s son. One of the best things about these family photo session proposals is being able to see everyone’s reactions and feel the love in their congratulations.

Family photos of a blended family before proposal

Family photos on West Maui beach

Father and son smile on the beach

Couple smiles for the camera right before proposal

Jamin turns to Lyndsay and puts his arms over her shoulders before getting down on one knee

Jamin gets down on one knee on the beach and Lyndsay looks into his eyes

Jamin proposes on Maui beach with ocean and bluff in the background

Lyndsay stares into Jamin's eyes as he is down on one knee

Lyndsay kisses Jamin as he is proposing

Lyndsay answers Jamin's proposal with a yes

Lyndsay hugs Jamin while he is still down on one knee

Lyndsay locks eyes with Jamin after agreeing to be his wife

Lyndsay's family watches as she gets engaged on the beach

Families react after Lyndsay says yes to Jamin's proposal

Lyndsay and Jamin look at photographer after she realizes the family photo shoot was a set up for her proposal

Lyndsay and Jamin walk back to family after he proposes

Lyndsay's mom admires her new engagement ring

Lyndsay's stepdad hugs Jamin after proposal

Jamin hugs his future mother-in-law after proposal

Lyndsay is congratulated by her sister after proposal as other family members look on

Close up of thin ring box with Lyndsay's name engraved

Jamin carries Lyndsay and they kiss on the beach

Jamin and Lyndsay smile at the camera as she rests her left hand with her engagement ring on his chest

Lyndsay with new fiance Jamin and his teenage son

Jamin with Lyndsay, her mom, sister, and niece

Jamin with his son and future male in-laws

Jamin and Lyndsay pose with Jamin's son and Lyndsay's brother-in-law, nephew, and stepdad

Lyndsay and Jamin walk down the boardwalk

Lyndsay and Jamin sit on the rocks and look at each other

Lyndsay and Jamin stand on the cliff as he kisses her forehead

Jamin hugs Lyndsay from behind as she leans into him. They close their eyes and turn their faces so their noses are touching.

Family present, photographer hiding

Maybe the family photo session cover story is not your style or something you think your sweetie would see right through. You can also use a different excuse such as watching the sunset before dinner. One family used the cover story that they had been to that beach on a visit years earlier and wanted to revisit it.

Since the photographer will be incognito and not able to direct you, we provide instructions on where family should be so they aren’t photobombing your proposal.

For Matt and Sara’s proposal, Matt asked his mom to take a photo of them right before he popped the question. Our photographer was waiting farther away at a different angle, so she could capture the proposal and Matt’s parents watching, without them blocking Sara’s reaction.

Matt proposes to Sara on the beach with his parents looking on

Maui proposal on the beach

Family is hiding

What if you want family to be there when you get down on one knee but you don’t want your sweetie to know they are there? In that case, loved ones should arrive to the proposal location before you two arrive, so they can witness the big moment but be hidden.

This plan requires choosing from certain locations and an additional fee.

The location needs to either have tree cover or somewhere family can hide without being seen or be a long beach where the proposal can occur at one end and family wait at the other end. An open space or a small cove with nowhere to hide won’t work for this type of plan.

An additional fee is also required for a proposal with a family surprise because a proposal planner will need to be on-site to meet family at the proposal spot, hide them, and cue them when to come out of hiding.

Speaking of coming out of hiding, family can run out of hiding right after you propose. However we love to do what we call a two-stage or even three-stage surprise.

In a two-stage surprise, you would propose and family would stay hidden while you start your engagement session.

Your fiancé then believes the proposal is the only surprise. But when the time is right and your photographer is ready, we have family come out of hiding so your photographer is poised to capture everyone’s reactions.

With the delayed surprise, your fiancé gets a little bit of time to absorb that you are engaged before loved ones come out to congratulate you. We also get two genuine reactions – one for the proposal and another for the family surprise.

A three-stage surprise fits when you are traveling with one side of the family and your sweetie knows they are on Maui, but you have other family or friends that are flying in for the proposal and your other half has no idea they will be here. The party you are traveling with would come out of hiding first and be in some photos with you. Loved ones who are arriving as a surprise would come out last and your sweetie will be blown away.

We did a three-stage surprise for Tim and Leesa’s proposal. First, Tim asked Leesa to marry him at sunrise. After a few minutes of engagement photos, Tim’s mom and sister came out to congratulate them. Just when Leesa thought the surprises were over, her mom and stepdad came out and she was shocked! It’s always been a dream for Leesa and her mom to visit Hawaii together and she didn’t expect it to come true yet – and to have their dream come true to celebrate Tim and Leesa’s proposal was amazing!

Tim proposes to Leesa on the beach with lava rocks in the background

Sunrise beach proposal with family surprise in Maui

Tim and Leesa hug after engagement on Maui beach

Tim and Leesa enjoy the sunrise right before family surprise

Tim's family surprises them after Maui beach proposal

Tim's family surprises them after getting engaged on Maui beach

Tim and Leesa pose with his mom and sister

Holding each other, leaning up against lava rock

Twirling in the shorebreak on the beach

Sunrise beach engagement session

Family surprise after beach proposal on Maui

Leesa hugs her mom after she surprises her following proposal

Leesa hugs her mom after she surprises her following proposal

Leesa shows her mom her engagement ring

Tim hugs Leesa's mom. Leesa hugs her stepdad.

Tim and Leesa pose with her mom and stepdad

Tim chose to add leis to their engagement session. We did a twist on a lei exchange, a Hawaiian marriage tradition where the couple gives leis to each other’s parents to symbolize the joining of families. Since both moms were there, we had Tim’s mom present Leesa with a lei and Leesa’s mom give Tim a lei.

Tim's mom gives Leesa a lei

Leesa's mom gives Tim a lei

Tim and Leesa kiss at the beach while wearing leis

Tim and Leesa pose with their families

Tim and Leesa celebrate with their families

Tim holds Leesa from behind and kisses the side of her forehead as they stand on the beach in the morning

Sometimes, we combine different techniques. For Giles and Kesslee’s proposal, they were traveling with Giles’ family, so we used the family photo shoot cover story as an excuse to get them to the beach. We pretended the photographer was running late when she was actually already waiting on the beach. This gave Giles an opportunity to walk Kesslee down the beach “while they were waiting on the photographer.”

Kesslee’s mom and grandma flew in to watch the proposal. Kesslee had no clue they were on Maui, so they arrived to the beach and hid among the trees until after the proposal when it was time for the big reveal! Check their engagement story out here.

If you want family there after the proposal

What if family is here on island, but you don’t want an audience for the proposal? How you involve them depends on if you want them in photos or not.

Family arrives after proposal

If you want a private proposal but you still want family photos, the best thing to do is select a proposal package with multiple locations and have loved ones show up to congratulate you at the second location.

With this option, and really any time you want to involve family in your proposal, please make sure you let your proposal planner know so we can write this into your itinerary. If family is arriving after the proposal, you may think we don’t need to know. However, in order for us to give you the best experience, it’s always helpful for us to know the full plan.

For Stephen and Brandee’s proposal, he got down on one knee and friends showed up later at their second location for celebratory photos.

Stephen and Brandee proposal on beach in Maui

Woman in floral dress reacts to proposal with tears in her eyes and hand over her mouth

Brandee wipes away tears after Stephen's Maui proposal

Couple reacts with smiles and tears after realizing there is a photographer there to capture their Maui proposal

Stephen and Brandee tear up after she accepts his proposal on the beach

Brandee takes a cell phone shot of her engagement ring in the foreground and her new fiance Stephen in the background

Stephen and Brandee kiss while holding her hand with her engagement ring out

Couple stand on a rock in the Maui shore break and kiss

Stephen smiles at the camera. Brandee stands in front of him and kisses his cheek.

Friends of the couple wait to congratulate them on the beach.

Couple walking towards waiting to congratulate them on the beach.

Friends of the couple hug the bride-to-be after engagement

Friends all gather around newly-engaged couple. Bride-to-be talks to baby.

Friends congratulate newly engaged couple and bride-to-be looks at the camera.

Three couples, one with a baby, smile for the camera. The couple in the middle just got engaged on Maui.

Three couples, one with a baby, pose for the camera. The couple in the middle just got engaged on Maui.

Family joins you at dinner

Some couples want to have the proposal and entire engagement session to themselves. Having family meet you afterwards at dinner is a nice compromise to have your privacy and still invite them to be part of your special night.

Recap of options when family is on Maui

Please let your proposal coordinator know if you are thinking of involving family and/or friends in your proposal. We can help you figure out the best plan and make sure your photographer is aware of all the details.

If you want family to witness your proposal and it makes sense for you all to arrive together, you can go to the proposal location under the guise of doing a family photo session. You can use another excuse if you want family to go to the location together but have the photographer to capture the proposal sneakily.

If you want loved ones to be there as a surprise, they would arrive early and witness the proposal from a hiding spot. This requires choosing from locations with somewhere to hide and an additional fee for an on-site coordinator.

If you want a private proposal, family should arrive at a second location, after you’ve already popped the question. Make sure to let us know, so we can coordinate the details and ensure everyone is on the same page.

If you want your photo session to be just the two of you but still want to celebrate with family, then loved ones should join you at dinner.

How can you involve loved ones in your proposal when they aren’t here on Maui? Check out ideas in How to Involve Family in your Destination Proposal – Part 2!

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