55 Ways to Pop the Question Memorably

Every couple is unique and every love story is truly one of a kind – so why is coming up with a way to pop the question so difficult?  You want it to be memorable; something that becomes a highlight of your shared journey.  At the same time, you want it to be something you can actually pull off.

Proposals on popular television shows and in movies always make it out to be a pretty slick operation.  From the bumbling-but-still-charming proposal between Mike and Phoebe on Friends to Derek’s ability to decorate an elevator AND ensure it was free when he wanted to propose to Meredith on Grey’s Anatomy, Hollywood has been setting the bar high for a while.

These days, there’s also a bit of pressure thanks to our addiction to sharing everything on social media.  I mean, c’mon, we live in a world where we post pictures of our breakfast in order to score some Likes – you can be we want to have something share-worthy once we’re engaged.

In fact, viral proposals aren’t that uncommon these days.

So if you’re looking for a way to pop the question to The One, we’ve got you covered.  From the romantic to the outlandish – check out our mega list of 55 Ways to Pop The Question.

1.  Back to the Beginning

Recapture the rush of emotions from your first date by taking your significant other to the place you first met or the location of your first date.  If possible, bring a memento of that date – a receipt, something you kept from that night or a photo you’ve had printed out.   Share your favorite memory of the beginning of your relationship and then say something along the lines of “This is where we met / fell in love and so it seemed like the perfect place to ask you to take the next step.”

2.  Make the Christmas Tree Really Sparkle

Proposing around the holidays is popular because many times, we’re already getting together with family and friends.   You can propose surrounded by your closest friends and family or you can pop the question privately and then share your news – and show off your ring – while making the rounds.  Choose a ring box that doubles as a tree decoration.  Once the gifts have been opened tell your partner, “Oh wait, there’s one more gift” and pop the question.

3.  Where Do You Want to Eat?

Call ahead to your favorite restaurant and ask about options for a proposal.  Many places will be happy to set the scene for you.  Have them serve the ring as a final course or incorporate your proposal.  Maybe pepperoni that spells Marry Me or a special bottle of wine with a customized label.  There are plenty of options and if you reach out to the staff ahead of time they can help you plan something memorable.

4.  A Love Story For the Silver Screen

Getting to a movie early can be a good move for a number of reasons.  You get your pick of the seats, you can settle in with your popcorn, snacks and soda without scrambling around in the dark.  But you can also take advantage of the ads that run before a feature film.  You can pay for a slot during their ad rotation.  Check with your local theatre for pricing and design options.

5.  The Friendly Skies

Plan a romantic getaway that requires you to fly.  Once you’re on the plane, recruit the help of a friendly flight attendant and clue them in on your plan.  Use the overhead speaker to declare your love and pop the question from the galley.  Then walk down the aisle, get on one knee and present the ring.   If you’re lucky, First Class might even donate a bottle of bubbly to celebrate.

6.  Morning Shows Make Happy Accomplices

Fun fact: In every city, morning shows on the radio have some fierce competition.   That means they’re usually only too happy to engage in an act or stunt that brings them some publicity.  Use this to your advantage and recruit their help with your proposal.  Have them call your significant other live on the air and tell them they’ve been selected to potentially win a trip or other prize if they answer one questions correctly.  Make THAT question your proposal!

7.  The Party Before the Party

Get your fiends together for a party and have everyone wear a shirt or hold a balloon with a letter on it.  Suggest a group photo with everyone in the right spot.  Take the photo, then ask your soon-to-be spouse for their opinion on the photo or have them come to the front of the group so they can see the message for themselves.  Pop the question and then initiate Phase Two of the party!

8.  Hopscotch and Happiness

Write your message out on the sidewalk with colorful chalk.  Invite your love outside to check out the message and then surprise them with a ring.

9.  Drop the Subtlety

On a random afternoon, start asking your partner’s ring size, what kind of gemstones they like and other obvious indicators that you’re shopping for a ring.  When they start to get suspicious and accuse you of ruining the point of a surprise proposal, pull out the ring you’ve already bought and say, “You’re right, try this one instead.”

10.  A Lifetime … of LOVE

Get your hands on a delivery box for a major appliance – a refrigerator, stove, dishwasher or washing machine.  Tell your partner you’re sending over a gift on a certain day so they’ll be home.  Attach a card to the box that says “Here’s something that will last a lifetime” and have it delivered carefully.  When they open the box, you’ll be inside ready with ring in hand.

11.  A Bit of Childhood Innocence

Put the ring into a box of Cracker Jacks or a Kinder egg.  Suggest the nostalgic treat while reminiscing about your own love story and when they find it, pop the question.

12.  Frequent Flyers

In couples where one person travels a lot for work, meeting up at the airport often becomes routine.  So why not take that simple activity and make it something memorable?  Team up with a few friends at the next pick-up.  Have each person holding a sign that spell out ‘Will You Marry” and then stand at the end with a sign that says “Me”.

13.  For Love Stories in Autumn

If you plan to propose in the fall, suggest a Jack O Lantern carving party with a group of friends.  Give each friend a stencil and have them carve a certain letter or word into their pumpkin.  At the end, line them up and make your proposal!

14.  Winter Wonderland

Build a small scene of one snowman proposing to another.  Ask your partner to check it out and when they see it or ask what they’re doing, have your proposal ready.

15.  Film Inspiration

Recreate a favorite romantic scene from a movie you both love.  Pretty Woman fans can show up in a limo with flowers, Say Anything groupies can stand out on the lawn with a boom box (Or MP3 player) and You’ve Got Mail admirers can meet in a coffee shop.  Whatever your Go To RomCom is, pop your proposal by recreating one of its most romantic scenes.

16.  Get Some Yard Work Done While You’re At It

Rake your leaves into piles or shovel a path in the show that spells out your proposal.  Invite your partner out to admire your handiwork and you can get points for doing some yard work AND being romantic!

17.  Holiday Showoff

String your holiday lights into a proposal.  When your partner comes out in the evening to check out the display, you’ll have created a proposal to remember – and one the neighborhood will enjoy as well!

18.  Trivia Night!

This is a great idea for couples with a shared love of board games.  Invite a few friends over for a game night and work your proposal into one of the games.  Make it your final question in a trivia game or a DIY card in Apples to Apples or Cards Against Humanity (assuming your partner has a sense of humor when it comes to that!)   You can decide whether or not to clue your friends in before you pop the question and have one of them film it on the sly for you.

19.  A Rose by Any Other Name …

Invite your partner to a local flower show or botanical garden.   Choose a time of year when at least one area will be in full bloom.  Once you get to that spot and the mood is perfect, surprise your love with your proposal.  Bonus points if you can then find a candle with the same scent to burn that evening.

20.  Under the Stars

There are plenty of amazing Dark Sky parks in the United States.  Pick a clear evening or suggest a romantic camping trip to one over the summer.  You can plan the trip to coincide with an annual meteor shower such as the Perseid Meteor Shower which happens every summer in August.  There, under the stars or with meteors passing overhead, ask the love of your life to be with you forever.

21.  Pick Your Own

Head out for a wholesome day of berry or vegetable picking at a local Pick Your Own farm.  You can usually choose from a wide variety of PYA farms so pick something you both love: Strawberries, blackberries, tomatoes or even green beans if that’s your thing.  Tell your partner you’ve spotted the most amazing bloom on one bush or tree and invite them over for a look.  Stash your ring there as they’re walking over and wait until they spot your sparkling treasure.

22.  Along the Beach

Write out a poem and your proposal on a piece of parchment and put it into a glass bottle with a wooden cork.  Plan a day out at the beach and place the bottle somewhere you’ll find it along a walk while your partner is setting up the picnic or simply otherwise distracted.  Suggest a short walk, “stumble upon” the bottle, open it and let them read it while you stand waiting with a ring in hand.

23.  Get Clever With Clues

Scavenger hunts are a great way to combine a bit of nostalgia with some creativity and enjoying some time outside together.  Come up with some clues that will take you all around your city.  You’ll definitely need some help with this one, as you’ll need your next clue to be kept safe until you get there.  Hit on places that were scenes for any major milestones in your relationship.  Make the final stop the place you want to propose and have the ring ready and waiting.

24.  A Friendly Waitress

If the two of you are regulars at a restaurant, work with your usual waitress or waiter to set up your proposal.  Have them comment on what a great couple you are through the meal and, at the end, have them suggest “You guys should get married!”  When your partner smiles, shrug your shoulders and say ”Maybe we should” and then whip that ring out!

25.  The Most Romantic Spa Day Ever

No one turns down a massage so offer the person you love a slow, sensual massage after a long day.  Create a relaxing atmosphere complete with candles, soft music and a comfortable space.  Work slowly, lingering over every inch of their body.  Talk to them about how much you love them, how happy you are being together and how happy you want to make them.  Once you’ve worked your way up to their arms and hands, do the right first, leaving the left hand for the very last.  Once you begin massaging that hand, pop the question and have the ring ready to slide right onto their finger.

26.  Say it With a Song

If you live in a city large enough to have public singers in the town center, take advantage of the moment while supporting a local artist.  Arrange ahead of time for one of the street performers you see regularly to be a part of the proposal.  If you share a special song, have them play that or simply a tune that can incorporate the question “Oh dear (NAME), would you marry (YOUR NAME)?”

27.  Cute Collar

If your partner loves stuffed animals and plushies, you can easily incorporate that into your proposal.  Buy one you know they have been wanting for awhile and simply attach the ring to its collar.  When you give them the present, they’ll be distracted by that certain something shiny and their new plushie will soon become one of the favorites.

28.  As the Ball Drops

Set your proposal for New years Eve and kick the year off right.  As the ball drops and people all over the world welcome in a New Year you’ll no doubt share a kiss with the love of your life.  Make it one to remember by whispering “Marry me?” as you kiss.  Have your ring ready for once the love of your life realizes what you just said.

29.  X Marks the Spot

Welcome the person you love home by leaving a trail of slower petals for them to follow.  You could outline the path with candles and have little gifts along the way.  Have a glass of wine poured and ready with directions to follow the trail.  You can add anything to the path – post-it notes with special memories or doodles, favorite candy, a trinket that represents an inside joke.  Have your path lead to a place where you can be ready and waiting with the ring in hand and the question on your lips.

30.  A Day in the Park

Head out to spend a day soaking up some sun in a local park.  Have friends and family nearby but out of sight.  Wait for a good moment and pop the question.  Then have your waiting friends and family come out from the woodwork for a surprise celebration.

31.  A Picture is Worth 1,000 Yesses

Hit up a local tourist place such as a zoo or open marketplace that has caricature artists.  Arrange with one of them ahead of time to do a special picture of the two of you.  He or she can draw you as they normally would and then include speech bubbles with one saying “Will You Marry Me?” and the other blank.  When they show the picture, have them mention it needs finished and let your partner fill in the blank!

32.  Have It All Fit Together

You can have jigsaw puzzles made to order through a number of different sites.  Work with a simple image editor or use the online tools provided through websites like Zazzle and Walgreens.  Design it to spell out your proposal and then challenge your significant other to a blind puzzle challenge.  Keep the ring ready and waiting to offer up as soon as the penny drops.

33.  Chocolate and Diamonds – Best Combination Ever?

Buy a nice box of chocolates.  And by nice, we mean, skip the Whitman’s Sampler Box and get over to a local chocolatier and plump for a box of high quality, proper chocolates.  Remove one and replace it with your engagement ring.  When they open the box, get down on one knee and ask for a piece of chocolate.  Then, of course, pop the real question.

34.  Picnic in the Park

A picnic outside is probably the most romantic meal in the world.  You can be totally alone, beautiful view and a hand-crafted meal.  It’s the ideal setting for reveling in the love you share and looking forward to your future.  Stash your engagement ring in with the dessert and top off your perfect afternoon with a perfect proposal.

35.  Skip the Coffee

Turn an average morning into one to remember!  Hide your engagement ring among the things you use every morning.  Hide it in the carton of eggs, tie it around the handle on the coffee pot, thread it around the controls on the treadmill.  When it’s uncovered, drop down to one knee and start your day by starting a whole new chapter in your life.

36.  For Frozen Fans

Food coloring makes it easy to write a proposal in the snow.  Sneak out early and write your message in a local clearing then suggest a cozy hike together.  Make your way to the clearing and get ready to pop the question with a dazzling, snowy backdrop.

37.  Get Into Character

Dress up as a favorite character – or one you know your partner can’t stand.  Surprising them with something silly will make it easier for you to pop the question since it takes away some of the pressure.  When my wife proposed to me, she came home with a dozen roses, an engagement ring and dressed in a panda suit.  Fun Fact About Me: I hate pandas.  So as soon as she came in, I knew something was up.  But the memory of how I had to say Yes to her and kiss her while in a panda suit is one that still makes us laugh.

Sand Heart

38.  At the Beach

Head out of a day – or an evening – at the beach.  As you’re walking along the beach, find a good sized stick and start dragging it along in the sand.  Stop every so often to draw a little something – a heart, a little house, things like that.  Stop again and tell your partner you want to draw them in the sand and tell them to pose looking across the water.  Instead, write your proposal with two stick figures and a heart and then tell them they can look.

39.  Good Things Come in (Progressively) Small Packages

What’s better than opening a large, gorgeously wrapped gift?  Opening one only to find another inside.  Gifts inside of gifts can be a great way to show your creativity and add some fun to your proposal.  You can wrap boxes inside of boxes and use fancy wrapping paper or even wrapping paper customized with your own photos and designs.  Alternatively, you can give them a set of Matryoshka Dolls, or Russian nesting dolls.  You can find stunning traditional options or quirky niche designs like zombies or aliens.  Put the ring in the smallest doll and when they open the final one it’s Showtime!

40.  Support the Local Arts

Many cities have small, local venues perfect for local artists looking to break into the music industry.  Check out who’s coming up to play and reach out ahead of the gig.  See if they’ll play a specific song or simply work in a proposal into their set.  Arrange for the venue to hold a celebratory bottle of wine and champagne so you can share a toast with the musician as well.

41.  Make it a Sweet Treat

Order a custom cake with your proposal written in frosting from a local bakery.  Ask them to display it in the front window.   Take a stroll for some window shopping and stop in front of the bakery.  Once they see the cake, take their hands in yours and propose right there.  Then step inside, pick up your cake and celebrate!

42.  Day Trippers

Spend a day sight-seeing in a nearby city or playing tourist in your own city.  Make it a real escape and rent a hotel room for the night, even if you’re staying local.  Work with the hotel’s concierge or guest services department to set the scene for your proposal.  Ask them to stock the room with a bouquet of your partner’s favorite flowers and a bottle of champagne on ice.  Pop the question and then toast the town!

43.  Enlist the Help of a Stranger

Head out to a place that has a meaning for the two of you.  Maybe the park where you arranged to meet for your first date, a favorite restaurant or any other place that has been an important place in your love story.  Remanence a little and then suggest getting a photo of the two of you together in this special place.  Ask someone passing by to take the picture but instead of posing, drop to one knee and pop the question.

44.  Spell it Out

Skywriting may be a bit extreme, but if you want to surprise your beloved with a message, there are still plenty of options.  Rearrange your fridge magnets and have the ring on one of the shelves inside – will they notice the front of the fridge before they open it or will they open the door, see the ring and do a double take?  Buy an extra set of tiles for your Scrabble board and hide the letters you need to spell out “Marry Me” and make it your first move.   Have a fake front page printed and slip it on top before handing them the paper in the morning.  Write your proposal on a small piece of paper and tape it over their backup camera.  Get creative and you’ll find plenty of ways to get the message across.

45.  Flash Mob

Use a local app to organize a flash mob to help with your proposal.   Check out online avenues to walk you through the Flash mob process or even to hire extras if needed.  Flash Mob America offers step by step directions and tips on how to make it a success.  Get a mob together and choreograph something simple that leads up to you popping the question.

46.  Ride into the Sunset

Rent a Vespa or a scooter for a fun day out.  As you’re preparing to set off, remind the love of your life to wear a helmet.  Of course, this will be a helmet in which you’ve already hidden your ring box.  Propose and then spend the day riding around the city to celebrate.

47.  Make Valentine’s Day Fun

Valentine’s Day can be stressful and so can proposals.  So combine the two and make it actually fun again.  Buy cute Valentine’s Day cards like the ones kids take to school.  Stash them all around the house on Valentine’s Eve.    No doubt your partner will smile as they see each one.  Have the cards lead the way to a simple box of chocolates – also with a kid theme.  But imagine their surprise when that simple box contains a few fancy truffles and … A dazzling engagement ring.

48.  Make It Sparkle

Set up a series of sparklers to spell out ‘Marry Me?’ a few feet away from where you and your friends plan to watch the fireworks or set off your own.  As the big show is winding down have a few friends help you to light the sparkers as quickly as possible then grab the love of your life and deliver your proposal with a shower of sparks.

49.  For Marching Band Fans

A lot of people love marching bands thanks to the popularity of The Ohio State University’s ‘Best Damn Band in the Whole Damn Land’ as well as mainstream hits like Drumline.  If the love of your life has a passion for marching bands, reach out to a local college or high school to ask how much it is to book them for a performance.  Have the band show up somewhere public light your partner’s place of work or a family gathering.  They can march in to a marching band version of your favorite love song and you can arrange for a drumroll once you pop the question.

50.  A Night at the Theatre

Hit up a production by a local theater group after arranging with the cast to propose after the curtain call.  This can be an especially great option for couples with a history in theater or simply a flair for the dramatic.

51.  A Room With a View

Fill a room in your home with pictures and mementos from your time together.  Cover every flat surface with photos and keepsakes.  Scatter more items on the floor and on any furniture in the room.  Get some balloons filled with helium and tie photos to the ends of the ribbons.   Make it a room absolutely stuffed in every dimension with things that represent your love story.   Once your partner gets over the shock of seeing so much in such a small place, pop the question that will help your love story grow.

52.  A Path to Matrimony

Line small votive candles to create a path to a large heart outlined in votives as well.  Be ready in the middle, down on one knee and ring in place.

53.  Sweet Dreams

Slip the ring onto your partner’s finger while they’re asleep.  When you wake up in the morning give them a lazy massage and start the day right.  They’ll notice the ring soon enough and then you can ask them to make your dreams come true.

54.  Splurge Without Leaving the House

Hire a personal chef for a night and create a truly 5-star meal in the privacy of your own home.  Invest in a high-quality bottle of wine or other favorite beverage and indulge.  Right before dessert, ask your partner to make tonight the night you start your new life together.  Then celebrate without worrying about how you’ll get home safely.

55.  Speak from the Heart

No matter what approach you decide to use for your proposal, speak directly from the heart.  If you choose to say something before you pop the question, keep it short, simple and honest.  At the end of the day, it’s a simple question and one that will create a moment you’ll both remember forever.

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