20 Ideas of How to Propose This Holiday Season

Ideas of How to Propose, Propose During the Holidays, How to Propose, Guestie

Need some amazing ideas of how to propose this holiday season? Did you know that nearly half of all proposals happen over the holiday season? Crazy right!? If you’re planning on proposing over the holidays this year, you’re probably not the only one who is trying to make it a forever kind of thing with their favorite person. But, before you get down on one knee, we wanted to give you a few options to get your creative juices flowing on fun ways to propose that will have your partner shouting YES!

1) Stocking Stuffer

High on the list of ideas of how to propose this holiday season, we love this super cute idea! Are you exchanging gifts together over the holidays? Stocking stuffers are so nostalgic and fun, aren’t they? They are also a creative way to propose! If you already have a ring, stick it in the center of the stocking between the other gifts. If you put it at the bottom, it’ll be highly visible and ruin the surprise. Layer your gifts so that when you are exchanging stocking stuffers over the holiday season your soon-to-be fiance will “stumble upon” the ring in between candy, gift cards, and the other fun little surprises you’ll have waiting for them!

2) Have a Picnic

Packed picnics are a romantic way to spend time together. It’s just the two of you, a bottle of your favorite drink and a basket or cooler filled to the brim with your favorite snackables. All you need is a blanket to lie on, a nice quiet spot, and a place to kick your shoes off. If you’re proposing with a ring,  you’ll have to decide if you want to pack it in the basket with the snackables or keep it on you for the right moment. You’ll already have the “celebration” packed with you in the form of your picnic, so after your person says yes you can enjoy the moment together privately. Selfies and FaceTimes to Mom are totally allowed!

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3) Take in the Sights of the City

Are you heading to your partners home town over the holidays for the very first time? They must be crazy excited to show you around the town they grew up in and give you a complete tour. Talk to their family about specific locations throughout the town where you’ll be sightseeing and your plans to propose. If you’ve never visited their town before, they’ll be able to let you in on cherished memories and the locations they happened in. You and your fiance will have an amazing proposal story to share for years to come!

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4) During a Hike

Are the two of you super-active adventurers? Are your days filled with hiking trails, and exploring national parks? Maybe you both call the great outdoors your second home and you spend your time in between adventures mapping out your next big trip. Planning your proposal during your next big adventure is a no-brainer! Not only is it the perfect place to take the next step in your relationship with an engagement, but you can plan an adventure wedding as well! 

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5) Enlist the Help of Family

Are both of your families gathering over the holiday season? Whether you have family members coming in from out of town or larger-than-life family celebrations planned for the holidays, involving your family in the proposal is a great way to add in sentiment and heaps of fun. It’s also pretty much a ready-made engagement party too! Ask your family what their fun ideas are of how to propose and get creative! Maybe it includes family t-shirts, a coordinated dance, a serenade to a specific song, or the passing of a cherished family heirloom.

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6) During a Shopping Trip

Running out to do some holiday shopping, together? You can propose in the jewelry store. Or, you can make it cute and say something like “Oh yeah, I forgot there’s something in here I wanted to pick up!” Lead your fiance into the jewelry store and over to their selection of rings. Ask them which style they like the best and if they want to make this a forever kind of thing. They will totally be caught off guard by your seemingly run-of-the-mill shopping trip that ended in a proposal. Super bonus, if you’re not sure what type of ring your fiance has in mind, this will allow them to pick out a style without all the guesswork and sleuthing on your end.

Ideas of How to Propose, Propose During the Holidays, How to Propose, Guestie

7) Walking the Dog After Dinner

What couple doesn’t treat their furbaby like their baby-baby? Your furbaby is a member of your family and they should be part of the proposal. What is your usual dog walk routine? Do you both take your dog(s) for a walk after dinner? Or is there a specific park you like to frequent with your dog? Either of these options presents a great opportunity to propose to your beloved. Want to make sure your doggy is part of the plan? You can buy them a shirt that says “Will You Marry Mommy/Daddy”? Or, you can secure the ring box to their harness while your fiance is distracted and have them run over to your partner with it!

8) Hire a Proposal Photographer

Thinking about popping the question during a walk along the beach, or an outdoor afternoon at the park? Hire a proposal photographer! A proposal photographer will be there “waiting in the wings”, discreetly of course, for you to propose to your partner. They’ll capture every moment of the proposal from a distance to allow for privacy. Once you’ve popped the question, they’ll come over and introduce themselves to your partner and take a few more shots of the two of you together! After the proposal, you’ll both be on cloud nine and totally elated at your engagement. It’s a great moment to capture and look back on together over the years!

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9) At Holiday Dinner

If your family is your absolute world, and neither of you can imagine taking this next step in your relationship without them by your side, proposing over holiday dinner is the perfect option for you! If this sounds like the way you’d love to propose, you have a few options. You can wait until after the blessing (if that’s something your family does), or you can stand up and “toast” prior to the dinner. Your last option is to propose when everyone is going around the table describing what they are thankful for over the last year. You know your family best, so we’ll let you decide if you want to let them in on the proposal or keep it a surprise for everyone seated at the table.

10) Hire a Proposal Planner

Hiring a professional proposal planner is a great way to set the stage for a proposal. Have you ever seen those crazy gorgeous proposal photos on Instagram and wondered how the couple pulled it off? There are usually flower walls, balloon arches, candles, and glitter explosions everywhere. They used a proposal planner! A proposal planner will take your dream proposal vision if you have one and execute it to perfection. If you’re stuck on creative ideas of how to propose, they’ll run through some options with you by asking a series of questions. From there, all you have to do is pop the question!

Ideas of How to Propose, Propose During the Holidays, How to Propose, Guestie

11) Streaming Your Favorite Series

Every couple has “their show”, or shows. And for many couples, it’s the only time they can kick back in their sweatpants and shamelessly enjoy some takeout and a bottle of red. It’s the time of the day when you’ve unplugged and shut off the rest of the world. And, it’s quite possible the part of your day, the one you look forward to most. Yes, you can propose at home, on your couch, in your sweats, with a brown paper bag from Uber Eats in your lap. In fact, if you do, we’d love to see it! Upload it to your Instagram stories and tag us @lets.guestie so we can share in the joy of your new engagement!

12) Have a Party Waiting

Your family is in town, or you traveled to be with your family for the holidays. While everyone is together, it’s the perfect time to plan a surprise proposal with a ready-made engagement party waiting! Choose a spot nearby your proposal location to make it easy for your fiance to transient from “I just got engaged” to “holy cow everyone is here to celebrate”! There are no rules on your choice of location for the engagement party. Whether it’s at a family home, a sushi restaurant, a wine bar, or a private event space, you get to decide!

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13) Without a Ring

There is no rule that says you have to have a ring in order to propose. You can propose without a ring. Or you can propose with a ring that you picked up on the fly as a “placeholder”. Actually, if your fiance has something specific in mind that they’d like for an engagement ring, or you’re thinking about having one custom designed it’s better to surprise them with the proposal first and gift them the ring later. If you feel like you need “to have” something in order to ask them to marry you, you can use something as romantic as a gorgeous bouquet of flowers. If you are a super fun couple, you can use a bouquet of balloons instead!

14) Photobomb

This is a fun, modern way to propose, and it definitely takes some planning ahead! Have you seen proposal stories where the partner had the ring for a year and used it in a series of photos without their fiance ever knowing? It takes some skill to pull this off, but it can be done! It involves having the ring, or at least the box, and using it to “photo bomb” the photos you take together in the months leading up to the actual proposal. From there you can use the photos in an album to propose to your partner. Or, you can propose, down on one knee, and later present them with the album and talk about how you were able to pull off this amazing surprise.

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15) Faux Delivery

Hey honey, there’s a box at the door! Look, we’re not saying to actually ship the engagement ring to your house because that may be risky. But you can at least package it up and make it look like it was sent to your home and addressed to your fiance. You can include a handwritten letter in the box detailing your proposal with the ring underneath. Or, if you want to make it fun, you can put the ring in a box. Then put that box in a box, and so on. Kind of like nesting dolls. You get the idea!

Ideas of How to Propose, Propose During the Holidays, How to Propose, Guestie

16) When the Ball Drops

Have you ever heard the superstition that whoever you kiss at midnight on New Year is the person you will be lucky in love with for the rest of the year? If you are a romantic at heart, chances are you have. The excitement of ushering in the new year with a countdown, ball drop, and a flurry of horns and confetti is always an awesome way to welcome the new year. It’s also a great time to propose! If you’re attending a party with family and friends, let them in on your plans so that they can turn their attention in your direction after the confetti hits the floor. You can also enlist a close friend to be in charge of a champagne toast and make sure that everyone’s glasses are filled.

17) Walking in a Winter Wonderland

Heading out to enjoy the snow this holiday season? Sledding, skiing, snowboarding, or a fun snowball fight complete with a snowman-making contest, who doesn’t love frolicking in a winter wonderland? When the snow is crisp and makes that fabulous crunching noise under your feet, you can use it to set the scene of your proposal. Whether you’re on a ski lift or playing around in your backyard, there is nothing more magical than a fresh snowfall paired with a brand-new engagement!

Ideas of How to Propose, Propose During the Holidays, How to Propose, Guestie

18) By the Lights Display

Isn’t one of the best things about the holiday season all of the lights on display? The glowing lights all around us make everything feel so at peace. Does one of your holiday activities involve walking through a Christmas tree farm or heading to the lights display at your local park? These are both whimsical places to plan an unforgettable holiday proposal. If you want to use one of these locations to get down on one knee, kick it up a few notches! Bring along a fun prop like a custom tree ornament to hang from one of the trees. After your partner says yes, you can use the ornament in a series of selfies.

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19) At a Restaurant

Proposing at a restaurant is kind of a classic move when it comes to ideas of how to propose, but that doesn’t make it any less effective! Heading out for a romantic dinner together? Call the restaurant ahead of time and let them know the date and time of your reservation and that you plan on proposing. Enlist their help in getting the ring in a glass of champagne or on a plate of dessert. If you’re not sure what to do with the ring, the restaurant staff may be able to provide you with ideas of how to propose based on proposals they’ve helped orchestrate in the past. If you do include it in the food, make sure it’s in a very obvious place to avoid any cases of incidents. Nobody wants a swallowed ring or a chipped tooth!

20) Over Morning Coffee

Last, but not least on our list of ideas of how to propose this holiday season, is during your morning routine! Do you love spending your morning together over a cup of coffee? The world is still quiet and you get to ease into your day with each other over a hot cup of coffee, tea, or cocoa. All while preparing to face the day side by side. If your morning cup is a cherished part of your daily routine together, it presents an amazingly intimate way to propose. But, we recommend secretly telling your fiances boss that they’ll be taking that particular day off! You’ll want to spend the rest of the day together celebrating and reveling in your excitement!

Ideas of How to Propose, Propose During the Holidays, How to Propose, Guestie

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Now that you’ve read through 20 amazing ideas of how to propose this holiday season, which option are you going with?

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