in: Featured, People, Relationships

• Last updated: September 28, 2021

10 Holiday Date Ideas

Couple kissing while holding Merry Xmas's board.

Not to toot my own horn, but I think I’m pretty good at a lot of relationship stuff. According to Kate, I’m very supportive, respectful, and trustworthy, am able to be the rock in a crisis, and have achieved the tricky balance between being nice and being a wiener. But, as Kate can also attest, I struggle with a few things, and one of them is being romantic. I find it difficult to turn my thoughts and good intentions into spontaneous acts of affection.

Which is why I love the holidays.

This time of year takes all the work out of creating romance; the elements for it are already in place. We’re naturally feeling less guarded and cynical and are primed for bonding and cozy intimacy. Christmas lights and decorations set the scene and provide the requisite warm fuzzies. There’s magic in the air before you even lift a finger. The holidays are like a pool teeming with fish; all you have to do is let down your net to pick up a great bounty. The romantic atmosphere is out there; you simply need to take advantage of it. Here are 10 ways to do just that.

Looking at Christmas Lights

House decorated with Christmas lights in snow.

The warm twinkle of Christmas lights can set the heart of your special someone aglow and give you both the childlike feeling of magical possibilities. Ordinary houses and trees are transformed into something extraordinary.

Most towns have hot spots for Christmas light decorations. Some neighborhoods compete in an annual arms race to see which house can create the best display. Their neighborly pride is your gain. After you map out your route, create a holiday music mix that you can listen to while you’re driving around. You can never go wrong with classic Christmas crooners like Bing Crosby, Johnny Mathis, and Frank Sinatra.

Also be sure to check out the massive displays that are sometimes put on in parks by community organizations, where you can walk around in a winter wonderland of millions of lights. Check your local papers and ask your friends and co-workers to find out where they are. And try to go during the week as they can be especially packed on the weekends.

The final touch to this night of romantic holiday lights is a thermos full of thick, delicious hot chocolate.  Sip on it while you take in all the wonder. Your date’s heart will melt.

Holiday Baking

Couple smiling while eating cookies.

Man, I love Christmas cookies. Both the eating and making of them, and chances are your wife or girlfriend does too. Holiday baking is a fantastic date idea because it gives you a chance to work with your gal on a shared task, which in turns strengthens your bond and connection with her. And most importantly, you get a delicious treat to eat when you’re done!

To keep this date simple, stick with making one kind of cookie; I would vote for gingerbread men as wielding the cookie cutters and decorating the little guys is an enjoyable task. Invite your gal over (or go over her place=-she probably has the cookie cutters), turn on the holiday tunes, and start whipping up a batch. The oven won’t be the only thing warming up.

When you’re done baking, sit back and enjoy the fruits of your labor or make a plate and deliver them to a little old lady.

Ice Skating

Couple enjoying ice skating in city.

Re-create the romantic ice-skating scene between Cary Grant and Loretta Young in The Bishop’s Wife by taking your gal to a skating rink. Between the hand holding and the full body embraces needed to keep each other from “accidentally” falling, you’ll have plenty of opportunities to strengthen the physical and emotional bond with your date. Many cities-even relatively balmy ones-have outdoor skating rinks during the winter that play Christmas music while you glide through the winter air. If yours does, take advantage of it while you can. It’s way more romantic than an indoor rink.

Decorate the Christmas Tree

Couple decorating Christmas tree.

A Christmas tree will infuse your date with the sights, lights, and smell of Christmas. It’s a holiday date trifecta. Start the date off by taking your special someone to a tree farm to pick out your tree. When you get home with your tree, play some Bing Crosby, sip some eggnog, and start decorating. If you’re hanging childhood ornaments, share some of the memories you have them with your date. She’ll think you’re sweet. You can even do some flirty teasing by putting tinsel on her head when she isn’t looking.

When you’re done decorating, turn off the lights in the house and show her you’re not afraid to have fun like a kid by lying side by side together under the Christmas tree and gazing up through the branches. Romantic smooching is 100% guaranteed.


People having lunch in the hall during holidays.

During the holidays, the need for volunteers goes up substantially at food banks, soup kitchens, and clothing donation centers. They need more hands to handle the flood of donations that come in during this time of year. I know sorting cans of pumpkin doesn’t sound very romantic, but volunteering is a fantastic date idea, especially if you’re trying to figure out if she’s the one. You’ll get a chance to see your girlfriend in a different light. How does she treat others less fortunate than her? With compassion? Scorn? Does she whine when given an undesirable assignment or does she roll up her sleeves and get to work?

I definitely recommend doing the volunteering date after you’ve been with someone for awhile. It’s a little heavy for a first go round.

Christmas Movie Night

Couple watching movie on projector.

Instead of dropping a double sawbuck on taking your date out to the movies, stay in and watch some classic Christmas flicks together. Stock up on your favorite Christmas movies, make some hot cider, and curl up next to each other under a blanket for hours of holiday-themed viewing. Need some help on which Christmas movies to watch? Here’s a list of some of my favorites. Many of them happen to be romantic comedies. Bonus!

  • It’s a Wonderful Life
  • Holiday Inn
  • White Christmas
  • Miracle on 34th Street
  • The Bishop’s Wife
  • Elf
  • Peanut’s Christmas
  • A Christmas Story

Christmas Shopping

Couple smiling while holding Christmas presents.

I know. I know. Consumerism has been sucking the life and spirit out of the holidays for decades, but it’s okay to take a sabbatical from the high horse and enjoy giving and receiving a few gifts this time of year. When it’s not overdone, it’s really a terrific tradition, no? I personally quite enjoy Christmas shopping. Buying gifts for loved ones amidst the hustle and bustle, festive store displays, and Christmas music gets me right into the holiday spirit. I’ve been doing more online shopping these days, and while it’s convenient, it’s just not the same.

Both you and your main squeeze probably have some shopping to do, so why not do it together? You can help each other pick gifts out for friends and family while taking in all the sights and sounds of the holidays. And of course you can drop hints about what you’d like to get from her by pointing out things that catch your eye. End the date by going home, ordering take out, and wrapping the presents together.

Go see The Nutcracker or A Christmas Carol

Father holding his daughter on his shoulder.

If your lady is into ballet, take her to a performance of The Nutcracker. Yeah, it’s ballet, but it’s a) romantic and b) a holiday tradition, which makes it perfect for this list. I always thought the sword fighting rats were pretty cool as a kid and that crazy guy with an eye patch was bad-a.

Going to see A Christmas Carol also makes for a terrific date. Every time I see it, I leave with an uplifted heart and a ton of holiday cheer. Here in Oklahoma, a local theater does A Christmas Carol with an Okie twist. Instead of taking place in Victorian England, the play is set in Territorial Oklahoma right after the Land Run. Scrooge is some sort of cattle and oil baron and instead of plum pudding the characters eat corn bread. It’s a kitschy good time.

Holiday Bed and Breakfast

Husband playing piano for his wife.

This is a tradition my wife and I began while I was in law school. After the craziness of finals was over, we’d rent a room at a bed and breakfast near Oklahoma City for a night of romance and reconnecting. The bed and breakfast we go to is old and homey, and the charm is only heightened by the seasonal decorations. It’s a night of total relaxation. We’ll light a fire, watch some Christmas movies, and, well, you know.

In the morning, we’re treated to a holiday-themed breakfast of pumpkin spice pancakes and hot chocolate. After our little holiday getaway at the bed and breakfast, my wife and I always feel reconnected and filled with the holiday spirit.


Couples smiling while sledding down on snowy hill.

Emotionally charged moments between you and your lady friend create memories and increase bonding. The adrenaline rush from speeding down a snowy hill can jump start your relationship. When the first snow covers the ground, grab your gal and your sled, find a quality hill, and take her for the ride of her life (for those of you in warmer climes, there’s always ice blocking!). Finish the date by warming up next to a fire. Oh yeah.

Do you have any other holiday date ideas? Share them with us in the comments!

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