How To Propose During The Holidays

Are you ready to propose? The holidays can be a great time to get down on one knee. The celebrations are already in full swing so might as well add to the good cheer, right?

Proposing during the holidays can be a perfect way to create a once-in-a-lifetime moment during a special time of year, as long as you plan ahead and take complex family and travel logistics into consideration.

If you’re ready to take the next step, check out our tips below to make sure it goes perfectly!

Have a Plan

It’s always important to have a plan for when you propose, but especially so during the holidays. When you are faced with family expectations and obligations, celebrations with friends to attend to, extra stress and travel plans, a proposal can go awry more quickly than handing Grandpa too much spiked punch.

The last thing you want is your Mom scheduling a last minute dinner on your special night or a flight cancellation getting in the way of getting engaged.

Make a plan, then make a backup plan, and clue in everyone you need to help make it happen  (even the flight attendants if need be). Just don’t spill your big news to someone who can’t keep a secret!

Think of the Ring

If you’re buying an engagement ring, be careful with it and plan ahead. It may take longer than you think to get the ring of your dreams from a jeweler, so leave extra time for ordering and shipping. It can take anywhere from 1 week to 3 months!

Once you have the ring and you’re making your proposal plan, think long and hard about how you will get the ring there, where you’ll keep it, and how you will present it. Don’t slip it into your shorts pocket in Bermuda, 6 long hours before your proposal. There’s no better recipe for ring lost in the sand forever than that. You don’t want to be this guy.

Consider Their Wish List

Have you asked your future fiance about what they want in a proposal? Some people would love to be surrounded by friends and family as they get engaged, while others prefer to experience this intimate moment privately. Make sure you know what they want – you only get to do this once!

Be Thoughtful about Family

Chances are, you’ll be spending part of the holidays with family. Consider their feelings too. Does Mom want to know in advance that you’re going to propose? Is now a good time to take Dad aside to make your plans known? Should you surprise your family with the news on Christmas morning? Think about how you’ll involve them in your plans and break the news in advance so everyone is happy come the big day.


Good luck if you’re planning on proposing this season and congratulations!