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  • Writer's pictureWedding Day Diamonds

Planning Your Perfect Holiday Proposal

diamond and yellow gold solitaire engagement ring and diamond eternity band

The holidays, from Thanksgiving through New Year’s Eve, are the most popular time to become engaged. And this makes total sense! Families are gathering. Winter is enchanting. And what better gift can you give your special person than a promise to spend your life with them?

Perfect Holiday Proposals begin with knowing what your partner wants, and to help figure that out, all you need to think about are the Who, What, Where, Why, and When of proposing…


Will they want a private proposal, or will they want family and friends to witness their big moment?


Winter outdoor wedding proposal
Photo Credit: Joynoëlle Photography

It can be tempting to tell yourself you’ll propose Christmas Day, and then not think too much beyond that. Don’t make this mistake!

Winter holidays have a way of becoming very busy, and you do not want to rush your proposal because you’ve got to get to Grandma’s house by noon.

Plan your alone time right along with all your other holiday plans. That way, you’ll have given yourselves the space to have your perfect intimate holiday proposal.


family celebrating wedding proposal
Photo Credit: Rachel Lynn Photography

If you are going to propose in front of other people, say at a family gathering, make sure to ask the hosts. You want them to feel included in the excitement, and by asking, you eliminate the risk of anyone feeling like their gathering got overshadowed by your proposal.

Tell the people who need to know, but don’t tell everyone. (You don’t want anyone else’s awkward “I can’t keep a secret” chatter to ruin the surprise.)

Since the host will already know, get specific about when you will do it, and then ask your hosts to have their cameras ready to capture the big moment!


What is your loved one’s ring style? Maybe you’ll shop together for your ideal rings, or maybe your partner would rather be surprised. Even if you shop together, you can still bring an element of surprise to the ring by introducing a custom element, such as by engraving a special date or phrase inside the ring.

If you’re shopping together, finding the perfect ring will be a little easier. If you’re surprising your partner, ask yourself these questions to figure out their fashion sense:

diamond and white gold halo engagement rings with diamond shanks

1. What’s their style? Are they classic or cutting edge? Romantic or rock 'n roll? Bohemian or modern?

2. What sort of jewelry do they wear now? Gold or Silver?

3. Do they wear a lot of rings already? What do these rings have in common? (If you’re not sure what they have in common, take pictures and bring them with you to Wedding Day so our client advocates can help you discern your partner’s style.)

4. Does your person basically never wear rings? (They may want a simpler design.)

5. Are they nature-lovers? Consider lab-grown diamonds and recycled gold for a ring that loves the planet as much as they do!

6. Do they work with their hands for a living? If your partner is a nurse or a sculptor, for example, they may prefer a low-profile ring that doesn’t snag on gloves or get in their way.

7. Come to Wedding Day Diamonds, where our Perfect Ring Promise means you can buy your ring today and exchange it at full value for an entire year if anything about it isn’t exactly to your partner’s liking. This promise includes custom rings. The Perfect Ring Promise is, quite simply, the lowest-risk, highest-reward way to buy an engagement ring in today’s jewelry market.


Andrea Wagner Photography

Whether you’re proposing privately or in front of a crowd, get specific about where you’ll do it.

Maybe that’s on your favorite bench at the dog park, or maybe it’s in front the fireplace at your partner’s parent’s house. Maybe you want to do it at your favorite restaurant. Wherever it is, don’t leave the where to chance. Make sure the place you want to propose will be open and make a reservation if it’s possible to do so!

Photo Credit: Sarah Olfelt Photography


This is the sentimental part where you’ll tell your partner why you want to be with them forever.

If you’re having trouble coming up with the right words, give some thought to when you first knew you wanted to marry them, or when you first realized just how special they are. Tell them that story as you pop the question!


Even saying “Christmas” or “New Year’s” is a little too vague. Pick a precise moment. This is especially important if you want someone to be filming it.

Once you’ve decided exactly when you’ll do it, make some plans for the immediate after!

Clear the day of any non-celebratory obligations, have some bubbly, and get right now to enjoying your engagement!


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