Memorable Ways to Propose During the Holiday Season

Engagement season is here! Many proposals occur between December and February; with holiday parties and family gatherings filling up the schedule, figuring out exactly when, where, and how to propose can be challenging. We have some memorably romantic and fun proposal ideas to use if you're considering popping the question during the festive season—figuring out the best time to do it is up to you!

Propose During a Holiday Shopping Trip

Heading out for some holiday shopping together? Consider popping the question in a jewelry store. You can make it seem as though you want to go in there to look for a gift for a relative, and once you’re in the store, lead your soon-to-be spouse to where the rings are located. Ask about their favorite ring style and whether they would like to make this a forever commitment. Your seemingly ordinary shopping trip will catch them off guard, resulting in a surprise proposal. An added bonus: if you're unsure about the ring style your fiancée has in mind, this approach allows them to choose without the need for guesswork or detective work on your part.

Wrap the Engagement Ring Box Like a Regular Holiday Gift 

Give a holiday gift that exceeds all expectations—wrap the engagement ring box with the holiday wrapping paper of your choice and watch your other half’s face light up with shock, amazement, and sheer joy upon opening. If you choose this method, you may want to place the ring box in a larger box, surrounded with tissue paper to prevent rattling, effectively disguising it and maintaining the surprise. And if you really want to knock the ball out of the park, consider giving the ring accompanied by matching diamond jewelry—a bracelet, necklace, or earrings!

Twinkling Lights Proposal

Whether it's near the glow of the Rockefeller Christmas Tree lighting in New York City, the illumination of the National Christmas Tree in Washington, D.C., or a quaint local tree lighting in your own town or city, there's something inherently romantic about witnessing a beautiful tree come to life with brilliant illumination. Another twinkling lights proposal idea is to prepare a thermos of hot chocolate or coffee and enjoy a leisurely stroll around the neighborhood, taking in the festive lights and decorations adorning neighbors' homes. Wind down the evening by romantically proposing once you arrive at a picturesque spot. We suggest exploring the neighborhood light displays a week or so beforehand to strategically plan your route.

Have a Holiday Party with a Plan to Propose 

Whether you and your partner are staying in town for the holidays or you're traveling to be with family and friends, having a holiday gathering provides the ideal opportunity to orchestrate a surprise proposal, complete with a ready-made engagement party in waiting! Opt for a location close to your proposal spot to seamlessly transition from "I just got engaged" to "Wow, everyone is here to celebrate with us!" No matter where you choose to celebrate your engagement, whether it’s at a family home, a restaurant, a wine bar, or a private event space, the decision is entirely up to you to choose a place you and your partner will enjoy mutually.

Holiday Gift Treasure Hunt

Surprise your partner with more than just a fabulous gift by organizing a holiday treasure hunt. Hide numerous fun and meaningful little gifts that gradually build up to the grand reveal—a breathtaking diamond engagement ring! Each gift should reflect the theme of your uniquely incredible connection, incorporating keepsakes from your shared experiences, your partner’s favorite things, and items that you know your other half wants. Make the treasure hunt fun and sentimental by including a multitude of clues that reflect how well you know and love each other, emphasizing the amazing aspects of the life you share together.

Some Important Things to Keep in Mind When Proposing During the Holiday Season

• Before proposing, figure out whether your partner would prefer a private engagement or if they have always dreamed of being surrounded by family and friends during this significant moment. Some people may love hearing the long-awaited question at a holiday gathering, while others might lean towards a quiet, private moment between just the two of you.

• Choose the perfect moment. The holiday season is often filled with bustling activities, from extensive family gatherings to lively parties. It's crucial to carefully consider all potential scenarios to ensure that your special moment is not only magical and memorable but also practical for both you and your beloved.

• Enlist help and support from loved ones. It helps to reveal your plans to at least one or two close friends or family members who can be trusted to assist you in coordinating the proposal to make the magical moment extra special. With their help, you can ensure that the proposal goes smoothly.

• Ask yourself—is this the time of year and setting that you both prefer? Proposals should reflect the interests of both individuals involved—you and your significant other. In essence, your proposal should revolve around what brings joy to both of you, during a season, and at a location that holds significance for your relationship. For instance, if your partner is shy and prefers privacy, a public proposal may not be the best choice. Similarly, if you both dislike the cold, proposing in the winter just before January might not be the most suitable option.

• Sync your schedules. Familiarize yourself with your and her family's and friends' holiday plans to prevent conflicts or overbookings. It's crucial to ensure that your proposal doesn't overshadow (or get overshadowed by) a significant family event, such as your girlfriend's brother planning to propose on the same day—yikes! 

• Secure a proposal date and time. Concoct a made-up holiday plan to ensure your partner doesn't leave town or schedule anything during the time you plan to propose. Avoid creating an elaborate cover story that your partner will sense is fake, and be careful not to make promises you don't intend to keep. However, make sure they have that specific time reserved.

Still looking? We can help you find an engagement ring that will truly wow your better half! Contact us today to chat with our customer concierge team—they're here to answer all your questions and help you find the perfect ring for the love of your life. We also proudly feature a state-of-the-art engagement ring customizer tool—try it today!