Our Guide to Holiday Proposals

The holidays are one of the most special and romantic times of the year, and unsurprisingly peak proposal time. If you have been preparing to pop the question to your special someone, make this festive season unforgettable with the perfect holiday proposal.

Our Guide To Holiday Proposals


The holidays are one of the most special and romantic times of the year, and unsurprisingly peak proposal time. If you have been preparing to pop the question to your special someone, make this festive season unforgettable with the perfect holiday proposal. Not sure where to start or how to plan a holiday proposal? We will guide you through how to pick the perfect time to propose this holiday, how to find an engagement ring that she will love and how to craft a proposal that you’ll share for generations.

Our Guide To Holiday Proposals

  • When to propose over the holidays?
  • How to choose an engagement ring? 
  • Proposal planning tips

When Is The Best Time To Propose Over The Holidays?

We’re in the midst of the most joyful season of the year. With several beloved holidays to pick from, you may have asked yourself which is the best day to propose. Consider which holiday is the best for your heartfelt proposal.

Christmas Eve Proposal

Great for: starting the festive season off with a celebration

On Christmas Eve everyone is bubbling with excitement waiting for the most magical day of the year to arrive. You can surprise your bride-to-be with an early gift with an engagement ring inside. This way, she’ll be ready on Christmas day to meet up with friends and family to celebrate the engagement and show off her diamond ring. Proposing on Christmas Eve is a great way to start the holiday season.

Christmas Day Proposal

Great for: proposing on one of the most magical days of the year

Make this a Christmas she’ll never forget with a beautiful engagement ring tied to the promise of a loving marriage. When to propose on Christmas day? You have the option of wrapping the engagement ring and leaving it under the tree for her to open. Or getting down on one knee during during a Christmas day walk. Or even proposing in front of the entire family during your Christmas meal.

New Year’s Eve Proposal

Great for: a party atmosphere with family and friends

On New Year’s Eve everyone will be in high spirits and celebrating. You’ll likely be surrounded by friends and family with champagne flowing. As the clock strikes midnight you can get down on one knee and ask the long-awaited question. When she says yes everyone will be prepared with a toast, to make this unforgettable moment extra special.

New Year’s Day Proposal

Great for: a proposal symbolic of a new year and life ahead

By giving her an engagement ring on the first day of the New Year you’ll be creating a foundation built on optimism and love for the rest of the year and your future marriage. You and your special someone can begin the New Year on the most positive note and carry those sentiments throughout the year.


How To Choose An Engagement Ring

As engagement rings are a symbol of your love and represent the promise of life together, you will want to put a great deal of thought into picking the perfect ring. Consider the following two questions when shopping for engagement rings:

1. How much to spend on an engagement ring?

The first question to ask yourself is: “how much should I spend on an engagement ring?”. We’ve all heard the two months’ salary rule, however this is just not realistic for many people. As you may soon be needing to spending money on a wedding, new home and other expenses that come with newlywed life, on top of your current bills, you don’t want to start your marriage with engagement ring debt.

While paying for your engagement ring in full might not be possible, think about how much you can invest towards a ring each month. At myGemma we provide affordable payment plans for many of our engagement rings. With our monthly payment plans you can get her perfect ring without draining your wallet.

And speaking of stunning engagement rings at affordable prices, at myGemma, we offer pre-owned engagement rings at up to 80% off retail prices. Choose from brands such as TiffanyCartier, David Yurman and much more. Each piece has been authenticated by our team of geologists and jewelry experts. With free US shipping and a 14 return policy, you can feel confident that you are buying a quality engagement ring at unbeatable prices.

2. What’s her jewelry style?

The engagement ring will be worn by your partner every day and will likely become her most cherished piece of jewelry. She might have been dreaming of her ideal ring and dropped hints about her favorite engagement ring style.

Consider what kind of jewelry she typically wears. Does she favor yellow gold over white gold? Does she opt for simplistic or ornate pieces? She may have a Pinterest page that could give you good insight into her jewelry or even engagement ring favorites.

When it comes to selecting an engagement ring you’ll need to pick the following:

  • Center Stone: Will you choose a timeless diamond to adorn the ring or a colorful gemstone such as a sapphire or ruby?
  • Diamond Shape: What will the shape of the ring’s center stone be? A classic round, modern oval or maybe a daring marquee? The most popular diamond shapes are round, followed by princess cut, cushion, oval and emerald.
  • Setting: The engagement ring’s setting can come in various metals such as platinum, rose gold, white gold or yellow gold. You may also opt to have the setting adorned with diamonds to enhance the overall sparkle of the ring or opt to keep it sleek and minimalistic. A pave band (diamonds down the side of the band) is great for adding extra sparkle for the bride to be that loves bling. While a halo (diamonds around the center stone) make the main diamond look a lot larger.

Top Proposal Planning Tips

With the proposal day selected, budget ready and engagement ring in mind, all that’s left is the actual proposal. Our proposal planning tips will help make the endeavor less stressful and leave you feeling confident.

  • Prepare what you’ll say during your proposal ahead of time. If you leave it to the moment of, you might be feeling butterflies and leave out some heartfelt sentiments.
  • Tailor your proposal to specific memories, share how they made your life better and just how wonderful your future together will be.
  • Consider if your partner would prefer a shared or intimate proposal. After all, you can always share the news of your proposal with loved ones later.
  • If you decide to do a public proposal, especially one with a photographer, make sure that she feels and looks wonderful. You may want to treat her to a manicure before the event if you feel that is something that would be important to her on the day.
  • Don’t pop the question during another person’s event such as a birthday party, graduation or someone else’s engagement party.
  • Take advantage of the cheer and holiday festivities. You may decide to propose while ice skating, under a massive Christmas tree or in bustling holiday market, all with dreamy holiday lights and music in the background.
  • Remember, you don’t need a flash mob or dramatic announcement to make your proposal truly special. Sometimes just dropping onto one knee and asking “Will you marry me” is all your bride-to-be could have ever wished for.

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