Man Skills: Holiday Dating Ideas

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vintage couple kissing illustration merry xmas card

So now it is Christmas, the most wonderful time of the year. Well, just because a baby was born in a manger and a fat guy miraculously slides down your chimney with a big bag of stuff that doesn’t mean that romance has to go out the window. During the holidays, you can actually plan to turn up the wick on those romantic flames. This can be the most memorable time for your relationship — if you allow it to be.

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.

You might struggle with a few things, and one of them could be the art of being romantic. If you find it difficult to turn thoughts and good intentions into spontaneous acts of affection, maybe these ideas will help take the pressure off of what to do and say. Sometimes the venue can do most of the work for you and the chemistry can work from there. You may be miserable sitting across a table, making reservations or trying to plan an outing, but a simple jaunt to holiday festivity can do wonders for the two of you. You may not remember what was on the menu on a date, but you will never forget when you both fell on those ice skates and laughed all the way home.


Looking at Christmas Lights

christmas lights on country house postcard

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 or zoos 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


date3Don’t you just love Christmas cookies? Of course you do, especially when you get to pat the baker on the butt. 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 because 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

vintage couple 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

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.


vintage soup kitchen during holidays

During the holidays, the need for volunteers goes up substantially at food banks, soup kitchens, youth organizations 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?

It is definitely recommended that you do the volunteering date after you’ve been with someone for awhile. It’s a little heavy for a first go round.

Christmas Movie Night

vintage couple watching movie illustration wonderful life

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. To pull this off, you’ll have to add some amenities. Maybe a tray of her favorite candy laid out in a gorgeous spread. Springing for a couple of soft (velour) blankets and some mood lighting could help too. 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


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. Buying gifts for loved ones amidst the hustle and bustle, festive store displays, and Christmas music gets one right into the holiday spirit. Lots of people have 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


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. 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. It’s also the perfect time of year to spring for tickets, dress up a bit and see how the other half lives. Not bad at all.

Holiday Bed and Breakfast


This is a tradition many married couples should consider adopting.  After the craziness of shopping is over, rent a room at a bed and breakfast near your city for a night of romance and reconnecting. The bed and breakfast idea 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, you’re treated to a holiday-themed breakfast. After our little holiday getaway at the bed and breakfast, you and your wife will always feel reconnected and filled with the holiday spirit.


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.

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