15 Proposal Ideas That are As Sweet As They are Creative

July 25, 2020 | riley

photo by Henry Tieu

So, you’ve decided to pop the big question? Congratulations! Let’s pause and have an internal “Woohoo!” moment (we don’t want to give anything away by being too loud, of course). If you’re reading this blog post, you are probably searching for the perfect way to propose. Before we get started here’s a little tip: there’s no perfect way! There’s only your way. Your proposal should be something that speaks to the two of you as a couple. Forget about “Instagram-worthy moments” and think about everything that’s led to this moment—your moment. Think about who you two are as a couple. If you’re still in need of a little inspiration after you’ve focused on yourselves we’ve got your back.

In this article you’ll find swoon-worthy proposal ideas for:

  • Proposing during the holiday season
  • Proposing at a sentimental location
  • Adventurous proposal ideas
  • Activity-based proposal ideas
  • Involving family and friends in your proposal

We hope these super sweet proposal ideas will get your creative juices flowing. We’re virtually cheering you on because you’re about to make the best decision of your life! We’ll see you on the flip side. Seriously—we have tons of wedding planning tips available to use after the big “Yes!” It’s kind of our thing.

photo by Jana & Simon Photography

Ideas for Proposing During the Holidays

Pumpkin carving. Tell your partner you want the designs to remain a surprise. Then, get to work carving “Will You Marry Me” or a design with a perfect ring-box-sized hole inside the pumpkin. When you’re both finished, reveal your masterpiece last!

Inside a holiday present. Strategically place the wrapped ring box under the tree (if you celebrate with a tree, of course). Make sure to tuck away the present so it’s the last one your partner finds. When it comes time to open gifts, wait for them to find “the one.” Pun intended. After they’ve unwrapped it—and just before they open the box—get down on one knee and pop the question!

NYE proposal. Is there a better way to begin a new year than with a wedding proposal? We don’t think so. Proposing at midnight on New Year’s Eve will never go out of style. Whether you’re celebrating with friends, having the time of your life at a city-wide event (post-COVID-19, of course), or cuddling on your couch watching the ball drop, be sure to have the ring ready when the countdown starts. Before exchanging your first kiss of the year, ask your partner to marry you as the clock strikes midnight!

photo by The Bold Americana

Still need a ring? We’ve got you covered. These 50 gemstone engagement rings are a millennial bride’s best friend.

Proposal Ideas for a Sentimental Location

Where you first met. As you get ready to start the beginning of forever together, it’s important to look back at your history as a couple. For a truly sentimental proposal, take your partner back to the place you first met or where you went on your first date. You can add a extra romance with a special little touch, like a bouquet of flowers but it’s not necessary. Reminiscing at the place it all began will make the moment truly unforgettable.

At home. Home is where the heart is, right? A proposal at home can be the ultimate gesture for your sweetheart. Here’s a fun idea: print photos of your dating journey and hang them up around the house like an art gallery. As your partner looks over the photos, make sure the last one they come to hints at the proposal (i.e. a photo of an unopened box or a blank picture). When they are about to ask what that photo is use it as your cue to get down on one knee and say the magic words!

Your favorite vacation spot. If you and your partner have traveled together (highly recommended), you probably have a few options to choose from. Think about your favorite trip, their favorite spot, or the most memorable vacation you’ve been on together. Spending time together in one of these places will already have romance filling the air. The proposal will be the icing on the cake!

photo by Through the Glass Paris

Adventurous Proposal Ideas

A surprise trip. A surprise trip might be the ultimate big-hearted gesture—just make sure your partner likes them. Depending on your budget, this could be a day trip, weekend getaway, or a week-long vacation. For a weekend getaway, book a plane ticket or plan to hit the open road for your trip. Tell your partner to pack a weekend bag. They’ll only need to know the weather forecast so don’t give them any other clues. For a week-long vacation, call your partner’s work and request the week off (without them knowing, if you can). Pack their bag, and wait for them in the parking lot on Monday morning when they arrive at work. Instead of heading inside, you’ll be heading straight to the airport for the best surprise ever!

During a photoshoot. Wedding photographers who put together styled wedding inspiration photoshoots are often looking for totally in love models to pose as their couple. If you want to really “wow” your partner find a photographer on board to help you pull this off! Keep in mind: this is ultimately your shoot, so you should come prepared with a budget in mind for their services. You’ll both be dressed up, the scene will be set, and every moment will be documented—what could be better?

On a hike. Adventure can come in any form or fashion. If simple gestures are more your speed, then a casual hike could be your plan! Plan to hike to a beautiful look-out point and time it so you arrive just before sunset. When the sky begins to transform into a colorful masterpiece, that’s your moment to express your deep love and take out the ring you’ve been hiding! Can you picture it now?

Wondering how to hide the ring? We’ve found the perfect ring boxes to keep your investment safe and hidden until the big moment.

photo by Chuy Photo

Ideas for Activity Based Proposals

Scavenger hunt. Set up a scavenger hunt with clues that lead to some of your favorite places around town. Choose places that are significant to your relationship or your partner’s favorite things, such as the place of your first kiss or their favorite coffee shop. Coordinate with shop owners and friends to hand them the clues when they arrive. You can also include a small gift or token at each stop (if gifts are your thing, of course). The final clue should lead to where you are waiting with the ring and one final riddle that pops the big question.

Within a custom puzzle. Do you love to do puzzles together? Order a custom puzzle on Etsy to ask the question for you! Use a photo of you two, a photo of the ring, or a photo of you holding a sign that reads, “Will You Marry Me?” Then you can plan to spend the evening snuggled up, listening to your favorite music, drinking your favorite wine, and putting the puzzle together. If any hints are included in the puzzle try to hide those pieces until the very end. Let your partner put the final pieces together for your sweet surprise. Be sure to have the ring ready when they realize what’s happening.

A love song. Love songs just hit differently, right? Even if you’re not a musician, there’s something heartwarming about writing a song for your boo. If you’re lyrically gifted you can also write the song yourself to sing. Grab your instrument of choice (or have a friend accompany you) and pour your heart out. Fun twist: make it a karaoke night for a more light-hearted rendition.

photo by Liv Schultheis

How to Include Family and Friends in Your Proposal

A picnic in the park. Ask a friend or family member to set up a picnic in a park and have your group hide somewhere nearby. Plan a long, leisurely walk that ends at the picnic location. After you’ve enjoyed a bit of your picnic, raise a toast to your partner, and pop the question. After they say, “Yes!” all your friends and family can come out to congratulate you immediately! Pro tip: ask one of them to record it so you can relive the surprise forever.

With your furry friend. Our hearts melt when we see a furry friend incorporated in any Junebug couple’s love story. When you’re both at home, excuse yourself to a different room and bring your dog (or well-trained cat) with you. Secure the ring box to their collar and send them into the other room to find your partner. If you’re confident your pet can immediately go deliver the ring, wait just out of sight until your partner finds the hidden treasure. If your pet isn’t quite so focused, pick them up and place them on your partner’s lap for a memorable cuddle!

Throw a party. If you know your partner would want to share the joyous moment with everyone you love, plan an engagement party for the same day! This takes some extra planning, so you might need to ask for help from some of your most trusted family and friends, but the look of surprise on your partner’s face will be worth it. Ask your friends to set up the party while you’re out popping the question. This is the perfect option for couples who want the actual proposal to be private but want to celebrate immediately after! Helpful tip: Give your partner a reason to dress up, so they’re party-ready!

Proposal Inspiration from a Real Couple

From the bride: Typically, I am the planner of the two of us, which led me to be worried about how Jess would pull off such a large surprise like a proposal. Jess sent me his work schedule, which showed me he was working all day Saturday. My high school friend asked me to hang out on Saturday, so I thought nothing of it. We were going to see a movie and talk over coffee. I had just worked out that morning…and was not looking proposal ready. My mom hinted that I should put some jean shorts on instead of my sweaty workout clothes—which annoyed me—but I complied.

At the coffee shop, my friend got a new camera and really wanted to take some pictures. Pictures are not my favorite, so after an hour of that, I was exhausted! A fake phone call from her mom asking us to pick up something she had forgotten led us to Jess and I’s favorite place in our home town. We spent most of our days at this coffee shop—dreaming about our future together, deepening our relationship, giving thanks for where we came from, and how far we have come.

As we drove up to the top of the parking garage, I began to see the most beautiful setup and my favorite person waiting to get down on one knee. Overlooking the Fort Worth city skyline, Jess asked me to be his wife, and I could never have planned a more beautiful moment. I will always hold this place as close as the memories Jess and I have here. Three years of long distance dating led us back to a place where we felt like ourselves and where we felt at home.

photo by Marissa Nichole Photography

Once the deal is sealed, remember to schedule an engagement session to mark this special time of your relationship! We’ve got all the inspiration and ideas you need right here:

8 Tips for Nailing Your Engagement Photos

We’re Just Crazy About These Fall Engagement Outfit Ideas

Everything You Need For Your Cozy At-Home Engagement Shoot

photo by Jana & Simon Photography

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  1. Please stop telling people that wedding photographers are ALWAYS looking for models. While we do occasionally, it’s important to remember that we do this for a living and can’t give every session (even surprise proposals) away for free. We deserve to be paid a living wage and encouraging people to look for free sessions is extremely un-professional and unethical.

  2. It’s very nice and romantic collection of proposal photos.

  3. Thanks for sharing such great ideas. It is very helpful for me because I planned to propose to my girlfriend but I’m confused about what I do that makes her happy and this day is unforgettable for me and her.

  4. These are all great ideas! I love capturing proposals on a hike.

  5. I like all the proposals wedding rings

  6. All these proposals are soo beautiful! I can’t choose!

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