Holiday Dating Prompts Interesting First Date Questions

OK, you survived Halloween and Thanksgiving; but now the Christmas and New Years holidays beg some new first date questions. Here are some helpful holiday dating tips.

Holiday dating

Holiday dating possibilities may actually be more promising than expected.

Truth is, dating may actually be facilitated during the holiday season: things to talk about during dates (funny family stories, traditions, etc), overall happier people, seasonal activities, and so on. Indeed, having a first date during a time that associated with togetherness and family bonding might make it easier for you to make that personal connection.

In addition, because family’s traditions often form a base for one’s behavior during the holidays, a first date during the holidays can offer a revealing opportunity to look into relevant early childhood experiences that contribute to the character and personality of your prospective suitor. So, should you venture out into the midst of the holidays to meet a romantic someone for the first time, one of the most important (pre-) first date questions you might ask is, “what are we doing; where are we going”?  A date destination is a window into what your mate likes/dislikes.

Here are some broad interpretational guidelines to holiday dating; these first date ideas should not be taken as distinct, hard and fast categories, but rather may actually overlap considerably as fun first dates:

(1) If your partner chooses a first date scenario that in some way (or ways) focuses, reprises or reminisces years-earlier Christmas experiences, then sentimentality, nostalgia, desire for childhood (or childlike nature) and/or tradition may form important components of their character makeup.

(2) A tendency toward physical closeness, coziness, romance (It’s nice to warm up by a fireplace with someone) and/or a touchy-feely nature or character (i.e. warmed by closeness) may be revealed by a first date scenario that emphasizes the seasonality of a cold weather environment.

(3) A first date with a focus on a Christmas tree suggests traits of romance and domesticity, a homebody (home & hearth), and/or indications of a strong female/maternal side.

(4) A holiday party first date can indicate a life-of-the-party personality, social seeker, someone who particularly thrives in a crowd situation, or who often needs people around them (for various reasons).

(5) A first date scenario that involves a focus on holiday music, shows or lit-up stages suggests the qualities of creativity, flamboyance, festivity and/or ability to appreciate, even flourish in unstructured situations.

(6) A holiday first date with a strong theme or focus on light or lights can indicate a need or desire for illumination, clarity,  safety, truth or even a connection to the supreme internal sense there is a God. Thus, your date may be a person who might be strongly spiritual or, on the other hand, perhaps a little lost or in the dark…. seeking clarity.

That said, lets look at some festive, seasonal first date ideas, and how they might fall into, or straddle these categories.

1. The Christmas Market Datetradition, nostalgia 

Holiday dating

Christmas market in Vancouver BC

Many major cities have Christmas Markets where there are usually stalls of Christmas ornaments, artisan gifts for sale, hot cider, sausages, live music, and general Christmas cheer. You can speed through a Christmas market pretty quickly, so this is the ideal weeknight date if you can spare half an hour after work, before dinner. Even if you get food, stop and listen to the music, and look at every single booth, you probably won’t want to stay for more than an hour and a half, so plan a second activity in case the date goes well. You may even challenge each other to pick out a perfect (or cheesy, or grotesque) ornament for each other, with a $10 budget. One day, you may be hanging those ornaments with your kids and telling them about your first date. This idea is a really inexpensive first date: free to walk around, and cup of cider or cocoa shouldn’t set you back more than $4 each.

2. The Christmas Music Datecreativity, festivity
Most churches invite the public in for holiday concerts, so check the local schedules. If you live in a bigger city, you can attend a performance of Handel’s Messiah or The Nutcracker Suite as performed by your local symphony, or maybe a Pops Concert of some sort playing more modern Christmas music. Check out a little pre- or post-concert champagne at a nearby hotel bar that’s all decked out for Christmas. Church concerts are free (but it’s nice to put in a few dollars when they pass the basket around for offerings).

First date questions

Handel’s Messiah is a Christmas classic

3. The Light-Peeping DateSeeking clarity/truth, spirituality
Festive holiday light displays seen after Thanksgiving are all the rage and offer fun opportunities for seasonal nostalgia dates with romantic overtones. Hop in the car (or take a walk, if it’s not too cold) and see the lights that cities, businesses and homeowners have put up to celebrate the holiday season. Taking a stroll through through lit-up neighborhoods with a cup of holiday Starbucks makes for a great conversation time. Many displays can be quite touching, especially at night, and going out is an excuse for a cup of hot cocoa when you get back home.


Holiday dating

Reindeer LED Christmas lights cheer the season

This is one date that’s more fun to do in the suburbs, so head out of town for an evening and drive around residential neighborhoods, looking for the most impressive displays.

Most towns and cities have one street where for whatever reason, neighbors really go all out, and a quick Google search should tell you where to look. If you’re carless in the city, a walk to look at the city lights can suffice, though renting or using ZipCar and heading out of town would really bring things to the next level. This idea is good for an hour or so, if you live in the suburbs, longer if you have to drive out to them. As long as the music and the conversation are good, a nice night drive can easily last a few fun hours.


4. The Ice Skating Datewarmth, closeness,  physicality
If you’re lucky enough to live somewhere where it snows on Christmas, take your loved out for a round of ice skating or sledding. These activities, in addition to providing fun for an afternoon, are sure to generate some memories, and a great way to break the ice both literally and figuratively speaking. Taking a date to the ice skating rink is a great way to develop trust and a sense of humility (depending on your skills). Ice skating is a fun way to get to know a person, and will also increase physical contact but not in a creepy way.

First date questions

Christmas ice skating can spark unexpected romantic opportunities.

If you’ve ever seen a romantic comedy, you know that holding hands while skating around an ice rink is the status quo during the holiday season. Don’t try to escape it: embrace it. Pack a flask with some spiked cocoa, head to the cheesiest, most overcrowded rink of all, and pledge not to leave til you’ve done a full loop, or heard “Jingle Bell Rock” played three times, whichever comes first. If you’re confident on your skates, a figure-eight or two never hurt anyone when it comes to impressing a date. This date idea is a bit pricy and will cost around $20, and skate rental will be about $10.


5. The Toy Store Datesentimentality, nostalgia, childlike
There’s a kid trapped inside of every adult, and visiting a toy store will definitely bring him/her out. Taking a date to the toy store is a bit unconventional but with creativity, it guarantees conversation and a good time. As long as you pick a time when it’s not too crowded, like late on a weeknight, toy stores are the best at Christmastime.

Holiday dating

Christmas toy store date is a return to childhood wonderment

Even if you don’t have a kid in your life, Christmas traditions always include charitable organizations such as Toys for Tots or Salvation Army’s Angel Program where you buy toys for children in need. Perfect excuse to check out all the awesome toys kids get to have now, under the guise of being philanthropic. Some Adopt-A-Family programs lets you deliver your gifts in person, an experience that’s sure to make the heart of any grinch grow three sizes that day. Expect to spend an hour or so shopping.


6. The Christmas Tree Datedomesticity, home body, maternal qualities
This is an adventure not for the faint of heart, but if you really want to make yourself appealing to a date, show of your outdoorsy, woodchopping skills. Many places in the United States have Christmas tree farms within a two hour drive or so, (and often much closer). At the farm, you’ll be able to choose a tree that’s still growing and then, yes, chop it down! It’s a lot of work, but you can reward yourself with hot chocolate and apple cider donuts which most farms sell.

Holiday dating tips

Christmas tree harvesting can be dating adventure.

If you simply aren’t in a position to go to a tree farm, going out to pick out a pre-cut Christmas tree can still be a pretty fun, if not quite as engaging, experience. This experience can take an entire afternoon/early evening, at least. But if you’re into the outdoors, it’s worth it.


7. The Anti-Christmas Dateindividuality, untraditional, eclectic 
Some days, some years, you’re just not into Christmas. If you’re feeling a little Holiday’d-out, escape the madness with an Anti-Christmas date. Head to a Mexican restaurant for ice-cold margaritas, chips, and guacamole. Go to a bar, preferably one not decked out with Christmas lights, and request all your favorite summer anthems on the juke box. Clear off the snow from your BBQ and grill up some burgers. Forget about Christmas altogether. Find a heated outdoor swimming pool or hot tub and go swimming in the cold. This is a great way to warm up a cool evening for moderate expensive, depending on how many margaritas you throw back.

Holiday dating tips

Mexican restaurants become new kind of Christmas traditions

8. Alternative Culture & Traditiondiversity, flexibility, creativity
The holidays are about tradition and culture, and that includes that idea that exploring different cultures is always an option. Restaurants with both traditional holiday favorites as well as culturally diverse menus are popular during the month of December. For instance, it you’re looking for Jewish Christmas ideas — as not many businesses are open on Christmas — try Chinese restaurants and movie theaters, jokingly referred to as “Jewish Christmas.” It is common for new movies to open on Christmas day, so take your sweetie out for a thriller and some dim sum after.


Holiday dating tips

Holiday window shopping makes a fun date at any age

9. The Window Shopping Datetradition, domesticity, childlike
Some people think that Christmas has become too much of a capitalist enterprise in the last 50 years or so, and maybe this is true, but at least stores make up for it by providing mind-blowing window displays, right? Take a stroll through the main shopping district of your town or city and check out the windows at major department stores. (Some have Christmas traditions that are unique to that particular location: Macy’s, for instance, has had renowned lighted window shows since 1956) Stores plan their Christmas displays months and months in advance, and the results are usually pretty spectacular. A hot toddy at the end of the night at a pub with a roaring fire place, or a hotel bar with a piano player singing Christmas songs. It’s window shopping — free!


Good holiday dating and happy holidays… and above all else…. let yourself believe….




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