50 Ways to Pop the Question

Because anyone can ask

Back in the dark ages, marriage proposals and proposal ideas were the domain of men. All women had to do was look surprised and say yes. But like many things that are now more equal, the proposal landscape has become a little less cut and dry. Both partners can do the proposing, but there are now twice the options (and sometimes twice the pressure). With the push to make even the smallest parts of our lives go “viral,” it can feel like you need to make something as big as a proposal Instagram-worthy. If a proposal happens but isn’t in your stories, did it even happen at all? Is it still a proposal if it’s not in a hot air balloon?

The answer is yes and yes.

Proposing can be a big, outlandish, emotional experience played out in front of a crowd of thousands at a Red Sox game. Proposing can also be a small, intimate, emotional experience played out in your living room in front of your pets. The point is for two people to make a promise to one another. So whether you got engaged on a gondola in Venice or the produce aisle of a grocery store, a proposal is just always just about two people. The mechanics of a proposal are deceptively simple. One partner asks another partner a question. The second partner answers. Ta-da! You have been proposed! And if feminism is your jam, neither partner is surprised by, “Hey I want to marry you.” So the where and when and how are just window dressing.

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But oh the window dressing! If you’re currently in the market for proposal ideas, what do you choose? There are simple proposal ideas, elaborate proposal ideas, viral proposal ideas, and surprise proposal ideas. But which one to do? Like any part of wedding planning (which is coming for you soon…) the best option is always you do you! But if you don’t know who “proposal you” is? Well, we asked wedding designer Jess Rutherford of Sentimental Fools for her top proposal ideas, both the intimate and the outlandish. Here, she’s given us ideas for every type of proposal possible. If you are big and elaborate people, we got you. If you are pajamas and brunch people, just keep reading. There’s something here for everyone.

A man proposes to another man in Paris for an adventure proposal idea

LOVE IS AN ADVENTURE Proposal Ideas

  1. Galactic Lovers: Plan a stargazing picnic and ask under the constellations.
  2. Sunshine of My Life: Sunrise and sunset make for stunning colors in the sky and the perfect backdrop for a proposal. Find a magical spot to enjoy the view!
  3. Disney Magic: Make your love story into a real-life fairy tale and propose in a Disney Park. (Pro-tip: You don’t have to go for Cinderella’s castle. There are plenty of picturesque spots around the park.)
  4. Written in the Snow: Write your proposal in the snow and ask from a ski lift, or the warm interior of the ski lodge.
  5. Footprints in the Sand: Write your proposal in the sand on a sunny beach. Pop the question before the waves wash it away.
  6. Room with a View: Stop to catch your breath at the top of a peak. Get down on one knee and ask them to turn around.
  7. Pictures Are Worth a Thousand Words:  Decorate a room with TONS of photos of you over the years. Make another moment worth capturing.
  8. #TBT: Revisit your relationship’s greatest hits—or just the site of your first date. Propose in the place where it all began.
  9. Rollercoaster of Love: Propose at the top or during the photo on the ride. (We recommend keeping that ring locked up or in a secure location during the actual ride.)
  10. Ferris Wheel: Take in the views below as you propose from the very top of the ferris wheel. Have your family and friends waiting at the bottom!

A man slips an engagement ring on a woman's finger as fireworks pop in the background for a seasonal proposal idea

SEASONS OF LOVE Proposal Ideas

  1. New Year, New Beginning: 3… 2… 1… Will you marry me?
  2. Be Mine: Why not fill a room with heart shaped balloons, roses, and boxes of chocolates and embrace the sentimentality of Valentine’s Day.
  3. Let Sparks Fly: Attend a summer fireworks display. Propose under the canopy of lights or with a simple handle-held sparkler.
  4. Jack-o-Lantern Love: Carve “Marry me?” into a pumpkin.
  5. Fall for Me: Go apple picking, pumpkin picking, or searching for fall foliage. Propose in the center of a corn maze.
  6. Deck the Halls: Have your sweetheart wake up to ornaments spelling “Will you marry me?” on a Christmas tree on Christmas morning OR while looking for the perfect tree. Bring a furry friend in on it with a present tied to their collar.

Fun and GAMES Proposal Ideas

  1. Play to Win (Their Heart): Catan, CandyLand, or Charades. Find a way to make sure a proposal is in the cards.
  2. Carnival Night: Make the ring the prize for winning the carnival game of your choice.
  3. Lucky in Love: Take them to a casino. Play the slots. No matter what, you are both about to win the jackpot.
  4. Love Hunt: Hide clues around town that lead them from one clue to the next (bonus points if you combine this with #7). The final clue leads to you and a big question!
  5. Coordinated Love: Make your proposal spot your next geocaching destination.
  6. Love and Basketball: Play a game of one-on-one on a court near your home. Make a new spin on H-O-R-S-E and play M-A-R-R-Y-M-E, putting your opponent’s spelling skills to the test.
  7. Take Me out to the Ballgame: Go classic jumbotron or take the kiss cam to the next level. For a nostalgic approach, hide the ring in a Cracker Jack box.

Candles are lit and plants stand by for a sweetest of proposal ideas

Sweet and Simple Proposal Ideas

  1. The OG: The classics never fail. Get down on one knee and ask away.
  2. I Woke Up Like This: Slip the ring on their finger before they wake up and see how long it takes them to notice. Or how many cups of coffee.
  3. Light up My Life: Fill the room with candles—the perfect lighting for love. Add some houseplants for an even more elevated look.
  4. Sentimental Spots: Head to “your” spot to make yet another memory somewhere close to your heart.
  5. Fortune Cookie: Make your own with a special question inside. Have them open yours the next time you order takeout.
  6. Creative Writing: Write your partner a poem or story titled The Story of Us. Make your proposal the final line.
  7. Time Machine: Recreate your first date, but this time with a new ending.
  8. A Toast: Slip the surprise into a flute of bubbles. Make sure they see the ring before bottoms up.

A couple video conference with parents notifying them of their engagement for a friends and family proposal idea

A LITTLE HELP FROM MY FRIENDS (and FAMILY) Proposal Ideas

  1. Puppy Love: Tie the ring or a “Will you marry me?” sign around your puppy’s—or really just any puppy’s—collar. Proposals + puppies = YES.
  2. Make the Kid Do It: Have a kid or niece or nephew? Put them in a proposal shirt and have them ask for a hug from your sweetie.
  3. Surrounded by Family and Friends: Turn a casual family gathering into a moment to remember and an impromptu engagement party. (Pro-tip: Make sure to clue in the host ahead of time!)
  4. Lettergram: Throughout the day have special people in your life deliver love letters you’ve written. The last letter is a special delivery from you, and it comes with a small ring-size package
  5. Next Item on the Agenda: Conspire with their boss and show up to their meeting in the conference room.
  6. Model for a Day: Have a photog friend ask for a favor to pose for some photos for their portfolio. Ask while the camera is clicking away.
  7. Surprise!: Throw yourselves an engagement party. Just make sure your new fiancé is the last to know.
  8. Make a Montage: Ask your friends and family to make a video of why they love you two together. Play the video and let your partner soak up all the love before asking the ultimate question.

A couple holds hands while walking towards a helicopter for a helicopter proposal idea

GO BIG FOR THE BIG QUESTION! Proposal Ideas

  1. Up!: Take your love to incredible heights and propose in a hot air balloon. (We know you all cried watching the Up! opening montage.)
  2. Movie Night: Take them to an outdoor screening of their favorite movie, or stage a proposal inspired by the silver screen. For your budget’s sake we hope their favorite flick isn’t Sweet Home Alabama.
  3. Rock of Love: Get tickets the next time their favorite band is in town. Get the lead singer to ask for you from the stage!
  4. Work of Art: Ask a local gallery to hang one of your own masterpieces in their gallery. Propose in front of the piece as you walk through the gallery.
  5. City of Love: Pop the question in Paris. Skip the top of the Eiffel Tower and go for something more off the beaten path. Why not give them a kiss and a ring in front of The Kiss in the Rodin Museum.
  6. Flash Mob: Get your friends and family involved. Pick your favorite song and dance it out.
  7. Northern Lights: Travel to the arctic circle to tell them you they light up your life under the Aurora Borealis.
  8. Heli-yes: Take a golden hour tour of your favorite town and pop the question against the skyline.
  9. Gondola Goals: Start forever in the canals of Venice in your own private gondola.
  10. Skywriting: Is there anything more over the top?
  11. Have a Proposal Off: Both want to get hitched? See who can top who with an all-out battle of the proposals. Everyone wins!

If you can’t choose just one proposal idea, there’s always the more-is-more option—just do all of them! Or as many as you’d like. My partner and I had thirty proposals—not one of them involved a hot air balloon. But that’s a story for another day.

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