The Holiday Proposal: 5 Tips to Make it Absolutely Perfect

The holiday season is upon us, and with it comes an extremely popular time of year to pop the question. Christmas Day is, in fact, the most popular day to propose (followed closely by Christmas Eve, New Year’s Day, and Valentine’s Day). We talked a little bit in a previous blog about what not to do when planning a holiday proposal, so let’s dig in to some things that you can do to make sure you plan the perfect holiday proposal. 

1: Scope out the weather & plan accordingly

Picture it: you’ve scouted the perfect proposal spot, you’ve scored the perfect ring, and you’ve thought of everything to make your big night go exactly as planned… or so you thought. As it turns out, you didn’t think to check the weather before heading out for the night. Now you’re outside and sure, it’s magical and all, but you are also freezing. If only you’d looked at your phone’s weather app before whisking your beloved away to pop the question! Depending on where you live, winter can be fickle — mild by day and frigid by night, or downright snowy and cold all the time. Make sure when you pick your big date that you plan for the weather. Think hand warmers, scarves, and gloves — don’t be afraid to get creative and work a steamy mug of hot cocoa in there somewhere. (Just… not in the actual proposal itself. Please. Not a good idea.) 

2: Embrace the season — be creative, not cheesy!

Twinkling lights, snowy banks, and Christmas carolers can really add to the magic of the season… why not use these once-a-year elements in your proposal? Don’t be afraid to embrace the season and work it into your proposal — just don’t get super cheesy or weird with it. Sleigh rides, yes — sitting on Santa’s lap, not so much. If you’re planning a public proposal, make sure your honey’s okay with it. Not everyone loves to make a scene. (Recreating that one proposal scene from Love, Actually may not be everyone’s cup of tea.)

3: Enlist plenty of help

Things are a little different this year, of course, but that doesn’t mean you can’t still enlist the help of friends and family. Conspire with their besties to send your beloved on a scavenger hunt or get creative with a socially distant Zoom call where their closest family can be a part of the magic moment. Friends and family can be your best secret weapon when pulling off a holiday proposal they’ll never forget!

4: Hire a photographer to capture the moment

Everyone knows to hire a wedding photographer, but few think about hiring one for the proposal!

Once you’ve planned the perfect proposal and everything is at the ready, don’t forget to capture the moment so you can both look back on it for years to come and smile. If the photographer is someone your soon-to-be-fiancé knows, take care to tuck them away until the big moment arrives so they don’t spoil the surprise with their presence! 

5: Relax and take it all in

Even with proper preparation and planning, things can go unexpectedly awry. If something doesn’t go quite according to plan, don’t sweat it — roll with the punches. Remember, this is a big, special moment but what matters is that your proposal is sincere and from the heart. Embracing what life throws your way can only lend beautiful authenticity to the moment and make it even more memorable. If something unexpected happens, don’t stress — laugh it off and carry on. You’ve got this!


Whether you pop the question at Christmas or wait until Valentine’s Day, planning is the key to a successful proposal. While planning, don’t forget something extremely important: a jewelry insurance policy that’ll cover your beloved’s diamond engagement ring! At Zillion, we offer comprehensive, standalone jewelry insurance policies that cover your jewelry in the event of theft, loss, accidental damage, or natural disasters. With jewelry insurance coverage from Zillion, your sweetheart will do more than just wear their jewelry — they’ll wear it with confidence.

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Zillion partners with jewelers to offer their customers lower rates on jewelery insurance. If you don’t see your jeweler on our list, we’re sorry, we won’t be able to offer you a quote for insurance.