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Ways to Pop the Question During the Holidays

By Catalogs Editorial Staff

engagementContributed by Info Guru Lindsay Shugerman

There’s just something special about getting engaged over the holidays. Maybe it’s all the sparking candles and pretty decorations. Or maybe it’s because Christmas and Hanukkah are times when families come together and memories are made.

But whatever your reasons for choosing this time of year, congratulations on taking that big step! Now to make it extra special, here are ten creative ways to pop the question during the holidays.


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10. Fill her stocking with hints…and something extra special in the toe

white christmas stocking

Stocking stuffers are so much fun to open because they’re all little, fun gifts like candy, toys, and of course, jewelry. So why not turn a Christmas stocking into a proposal? Fill her stocking with small gifts that hint at something special to come, like tokens from your first date, a split of champagne and something shaped like a heart (or even better two hearts.) Make the next to last gift something decidedly wedding-ish (a bridal garter, perhaps?) Save the best for last of course, with the ring in a box or bag tucked into the toe.

9. Spin the dreidel, she wins

orange and blue dreidels

After the Hanuakkah lights have been lit, challenge her to a candlelight game of driedel. Play for a bit with candy or nuts, but on one of the turns when she spins a Gimmel (which means take everything in the pot), slip her ring into the pile as you push it towards her.

8. Decorating the tree with a diamond

angel christmas ornament

No, I would not suggest that you hang the ring from the tree by itself. But you can put it onto an ornament and hang that. Tie the ring onto an angel ornament (she is your angel, right?), then hand it to her to hang while you’re decorating the tree. If you’re afraid she might not notice the ring, say something like “This is a special one, isn’t it?” as you hand it to her.

7. Go on a sleigh ride

couple on sleigh ride in snow

Sleigh rides are romantic to start with, but when you combine it with a proposal it’s pretty much the ultimate.

Schedule the ride for an evening, preferably a snowy one. Bring a cozy blanket for two, a thermos of hot cocoa, and of course, the ring in a box. Arrange with the driver to stop in a pretty spot, and then pop the question. Do not, I repeat, do NOT try this while the sleigh is moving! One bump and the ring could go flying!

6. On the eighth night

Hannukiah

Who says eight nights of Hanukkah presents are just for kids? This year, it’s about proposing!

Select seven little gifts that show her how much you love her. Her favorite candy. A trinket from a trip you took together. Something from your first date or a place that’s special to the two of you. A pair a toasting flutes. A locket with your picture in it. By the eighth night, she’ll be wondering exactly what’s going on…and oh how pretty that diamond engagement ring will look in all that candlelight!

5. Play Santa

Santa Claus

Santa makes dreams and wishes come true, right? Especially for good little girls. So why not dress up as Santa Claus and ask her what she wants for Christmas this year? After you hear her wishes (best done in private, of course), tell her you have a little present for her. That’s the time to pull out that little velvet box and get ready for the biggest hugs and kisses Santa ever got!

4. Custom filled crackers

christmas crackers

Christmas and New Years crackers are tradition in the UK, but they’ve become popular here in the U.S. in recent years, too. Get unfilled crackers, or buy a set and tuck the ring into one for your sweetie. When midnight arrives on New Year’s Eve or it’s time to open the crackers at Christmas dinner, hers will contain more than a toy and a riddle! (If you want, you can even turn the traditional riddle into a written proposal!)

3. Let Teddy help you out

Giant Christmas teddy bear

Take one giant teddy bear. Add the sparkle of a Christmas tree. Decorate with a box in teddy’s hand or a ribbon around his neck bearing the ring. Tuck teddy up against the tree late on Christmas eve, and wait for Christmas morning. Sometimes, a teddy bear makes everything just right!

2. Save the Date to see the lights

Christmas lights tat Temple Square

Walking around looking at the lights of Christmas is such a sweet part of the season. So why not turn that “Ooo! and Ahh!” experience into a romantic proposal. Select Save the Date cards for your wedding well in advance, and have a sample one to personally address to your intended. A special hand written note is definitely in order, here! Head out a night or two in advance and select an especially beautiful display as “the spot.” Then head out for a walk together, and just when she’s admiring the lights, give her a “Save the Date” she will keep forever.

1. Propose at church

midnight mass

If your faith is an important part of what brings you together, consider proposing just before or just after midnight Mass or Christmas eve services. What could be a better expression of your shared beliefs and your hopes for a long and wonderful life together?

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While the marriage is always more important than the proposal, it’s wonderful to make the asking memorable, too. Use one of these ideas or come up with your own special ways to pop the question during the holidays and you’ll have two things to celebrate this year!

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