The 8 Steps Of Holiday Dating

Depending on how much time you spend in coffee shops and retail stores, or with your family, the spirit of Christmas is eventually inescapable. And, unfortunately, the spirit of Christmas can mean anything from warm, cozy thoughts of friends and loved-ones to reckless consumerism, excess of sentimentality, and false love.

For the most part, it’s a wide array of emotions, hopefully more positive than negative. It can be rough-sleighing too, so it’s important to know what is real and what is influenced by this peculiar time of year. Just get through it with a couple new and exciting memories, and you’ve done well. Here’s what you can expect across the holiday season, some of which will linger longer than others, and some will happen spontaneously and then be gone. Good luck.

The Meeting

As we’ve discussed before, it’s pretty easy to meet people over the holidays. Plenty of those out socializing are single and many of them are ready to embrace the merriment, which will almost undoubtedly include some combination of alcohol, music, and dancing. Maybe there will also be something theatrical, maybe something cheesy and embarrassing, and maybe there will even be mistletoe (tip: do not bring your own mistletoe). Regardless, the nights should be at the very least interesting, taking on a different form than simply going to a bar or club. (Another tip: wear something festive, but not too festive. That ugly Christmas sweater should attract the type of person you want to be attracted to you.)

The Frustration

You’re going to have a lot of fun one night, and then you are going to go home alone, realize the New Year is one day closer, and accept you’ll be lonely and sad the rest of your life while everyone else is happy and having more sex than you will ever have. Maybe I’m writing this from experience, or maybe I just had a lot of fun and had to go home alone, but this isn’t about me. What’s important is that these beliefs are not true. Do not give into the dark side of your thoughts (I may have also just seen Star Wars). At best, these negative feelings are, like, a quarter true.

The Minor Victory

Then there will be another night — well, morning really. One where the pride you feel about the romantic accomplishments you had the night before is only paralleled by a hangover. Do not rest on your laurels. There is going to be a stretch of consecutive parties at some point during the holiday season. Whether they are planned or impromptu, of the family, friendly or professional variety, they are going to line up and test your mettle. And in order to truly get the most out of the romantic season, do not get complacent. Do not give in to a hangover or lethargy. Always go out. That’s pretty much 50% of the key to meeting people. You know what’s going to happen if you don’t go out? Someone else will. Suck it up.

The End of the Night

Things can get real tense real fast when a party slowly dies down and you have to lock up a victory (victory doesn’t mean taking someone home by the way – it’s getting a phone number, telling someone how you feel, or sure, taking someone home). Maybe there are four minutes left on the clock and you need to run the ball to secure victory, and maybe you need to pull out some desperate measures to make a stunning comeback. Either way, establishing that singular connection with someone –and whatever that may lead to – isn’t easy, but definitely important. Again, don’t let being exhausted or inebriated cause you to miss an opportunity. Serendipity may be the name of a silly holiday movie starring really attractive people, but it’s a notion to heed.

The Follow Up

Now to navigate the tricky waters of meeting someone, made all the trickier by the fact it’s the holidays and maybe people are heading home and maybe people have a lot of plans. Or maybe they are shaking up their lives. Or maybe they were just seeking one brief, escapist fun. So what do to? Well, the best start is to send a message the next day, something that is direct, somewhat open-ended, but doesn’t ask a specific question. Reflect on the meeting, but don’t dwell on it too much. You’re setting something up without making set plans. Really, no one wants to make any decisions or plans over the holidays anyway. Plant a seed, acknowledge the meeting, and wait until the dust (snow?) settles in the New Year and follow up again with something decisive.

New Year’s Eve

I would proudly argue this is a day above all others that is most stressful if you don’t have a partner. Valentine’s Day has nothing on New Year’s Eve. That’s because February 14, while commercializing itself as a romantic holiday (and being most abhorred by service industry folk), has drummed up a nice Anti-Valentine’s Day sentiment, where you can gather with friends and mock couples and schmaltzy, phony romance.

But New Year’s…that’s something on the calendar that is undeniable. Everyone (in the Western world, at least) celebrates it, and regardless of where you are, you know a lot of people are out and having a night. And when midnight strikes, people kiss and embrace, and it’s the first few moments of a New Year that, however arbitrary, come with a feeling of revival and opportunity. These can stick with you. So you don’t want to be alone.

Being with friends is probably the best option; especially a house party or pub devoid of excessive pretense and unrealistic romantic expectations. But should you be out, keep note of the time, put yourself in a good spot, and trust that someone else in the room is probably available for a midnight kiss. But if it doesn’t work out, it’s probably fair to say a fleeting moment of time won’t be indicative of the 365 days to come. Cheers!

The Relief

Some time on New Year’s Day, or maybe the day after depending on how late the night before went, you will breathe a sigh of relief that the over-sentimentalizing, the string of parties, the constant socialization, is all over. The cold and quiet of January awaits, which means it’s time to come up with a list of solid excuses for not wanting to leave the house so you can stay in and watch Netflix instead.

The Pointlessness

At least dealing with the chaos of the holidays keeps one from thinking of a bunch of resolutions for the New Year. Relationships, partnerships, hook-ups, liaisons….they come and go, regardless of the calendar. Seasons churn up feelings and excitement, but eventually everything settles into place. And you’ll have a good 11 months until more holiday fanfare. And stress.


Anthony Marcusa
Anthony Marcusa is a Toronto-based freelance journalist whose writing dabbles in film, TV, music, sports, and relationships – though not necessarily in that order. He’s simultaneously youthfully idealistic and curmudgeonly cynical. But he’s always curious.

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