The Single Woman’s Dating Playbook: The Christmas Cocktail

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If you’re single, hold onto your britches because we’re in this winter for the long haul.

I hate to report, but cuffing season is officially closed. Thank you for your valiant efforts during October and the better part of November but Thanksgiving has come and gone so if you’re single, you’re staying that way until the first spring buds pop out from the frosty grass. Or, for all three of our West Coast readers, until the fog lifts and the sand dries out.

Winter is here, and for the lucky ones that found a Hibernation Homie™, I tip my hat to you. You did it! You locked down another human being that would rather spend these frigid months eating pie and drinking boxed wine in bed than braving the elements for a $13 vodka-soda. This is your victory lap. You did good and I’m proud of you.

Am I also slightly jealous? Certainly. But cuffing has never really been for me. See, winter is by far the most tumultuous of the dating seasons and I like a good challenge. Plus, someone’s got to fight the good fight while all of you assholes snuggle.

For those locked and loaded as December approaches, I hope you read this series with your significant other whilst spooning a pint of mint chip. Go ahead, laugh at the absurdity of it all. Hell, make it a weekly tradition! Before you know it, an “I’m so glad that’s not me anymore” will slip out of one or both of your mouths and for a moment you’ll think, “Am I done forever?” Trust me, you’re not. That’s just the haze of dark liquor and sub-zero temperatures talking. Ride this winter out, player, we’ll see you again in the spring.

For those of you cuff-free this season, I see you. We are one. If we were together, I would look you knowingly in the eyes and whisper just loud enough for me, you, and the barkeep to hear, “We got this.”

Holiday season dating is not for the faint of heart. It is for the warriors, the dreamers, and the lovers of the chase. I beg of you, do not resign to a season of slovenly loneliness. Do not accept defeat because you are not defeated. Rise. Rise to the occasion with me. Together, we will take winter conquests by storm, page by Single Woman’s Dating Playbook page.

May I introduce our first play of the season: The Cocktail Challenge.

To properly deconstruct The Cocktail Challenge, I have to take you back to December 2015. I was single, living in Washington D.C., and truly fatigued from the notoriously brutal dating climate that is the transient, hyper-competitive population of our Nation’s capital.

The Analysis

This love story began as most of my eventual heartbreaks do – on Bumble.

Ryan was high energy, in a do-er kind of way. He was the planner, the “get off your phone and connect” type. Fueled by granola and IPAs, he was that skinny-strong guy that weaves his way in between pedestrians on the metro, his fixed gear bike held high above the crowd.

2015 Victoria was a marvelous match for Ryan. I too was high-energy, but in more of a night-classes, waitressing, dance-club kind of way. Over the course of our start and stop relationship, we’d learn we balanced each other out nicely.

Upon initial analysis, I knew I couldn’t phone this date in. Ryan was smart in the way most D.C. people are, current events and social justice were his thing. He was my type of person, hyper-driven but drank like a fish.

Ryan was complicated, he was multi-faceted, and he challenged me quite a bit. I knew if we simply went for happy hour, both of us would put on our people pleasing fronts and get nowhere. We’d try to out-charm each other and walk away unsatisfied, not having broken the surface.

I wanted to pick apart the layers of Ryan. What I really wanted was him to come over, sit in my living room, and talk to me for hours over a game of chess. I knew, however, the notion of doing nothing for a first date would scare Ryan shitless. Remember, he was the ultimate planner, a wonderful quality that would ultimately be our downfall. Ahhh, hindsight.

So, how does one plan a date intimate enough to truly get past the bullshit and understand a person, while also having enough structure to appease a schedule obsessed companion?

You employ The Cocktail Challenge.

Pre-Date Preparation

“Will you help me?!” I texted Ryan on Wednesday afternoon. Our date was planned for Thursday evening, with no real logistics in place.

“Yes ma’am,” he replied. “What’s up?”

“I have this holiday dinner on Friday night. I told them I’d bring alcohol, but now the host wants me to bring a Christmas-themed cocktail! I have no idea what to bring.”

“Well, you only drink martinis, so it seems you’re in a pickle. Unfortunately, I don’t know any good holiday cocktails either, I’m a whisky guy.”

Men. They always need prodding.

“I figured you also wouldn’t know,” I replied. “I’m going to make it an activity, finding the perfect holiday cocktail, want to be my official taste tester?”

“Absolutely. What can I bring?”

I instructed Ryan to meet at my house at 7:00 p.m. on Thursday evening. He was to bring candy canes, whatever almost-finished bottle of cheap liquor he had in his house, and a baguette (for sustenance).

During work that day, I googled three different holiday cocktails and picked up the ingredients on my way home. I lived in a house at the time, so most of what I had to buy was garnish, our bar always stayed pretty stocked.

When I got home, I changed quickly and turned the stove on because our first cocktail was a hot mulled wine. By the time Ryan arrived at my door (baguette in one hand, bicycle in the other), the house smelled like cinnamon, Christmas music played in the background, and I was giddy from all the damn holiday cheer I had just conjured with my own two hands. Plus, you know, my roommate was upstairs just in case Ryan turned out to be a serial killer.

Shoot Your Shot

I got Ryan in the kitchen immediately. Activities, like chopping and mixing, are fantastic ways to break the ice while still allowing for good conversation. Ryan and I joked, we taste tested, he touched my lower back while reaching for a spoon. I asked him to read me instructions while I searched for spices, he wouldn’t stop eating the candy cane garnish, etc. etc. etc.

An hour later, we had six drinks lined up on my kitchen table. We sat down across from each other to admire our masterpieces. There is a sense of comradery that comes with having made something together, I don’t care what it is. Hell, plan a date and make a birdhouse, doing something with your hands relieves the tension far more than staring at each other from across the bar.

Ryan and I spent the rest of the evening tasting our cocktails. Sure, the mulled wine was cold and he put so much grenadine in one of the drinks it could have lit a small house on fire, but we genuinely didn’t care.

After the second drink we moved onto the couch, relaxed and trying to pace ourselves Ryan managed to actually light the fireplace, something I was certain was an impossible task.

“So, he said, which drink will you bring?”

“What?” I laughed, brushing stray bark off his sweater.

“To the party?”

“Oh. Ummm, I made that up,” I admitted.

My stomach dropped, but I let the silence linger. I was curious, more than anything, how he would respond.

Finally, he smiled. It was a wide, head cocked to the side, “I can’t believe you did that” smile. But never the less, it was a smile. I knew I’d won this round.

“Well, how about this. I’m having a party next weekend and we could always use a good Christmas Cocktail. Wanna come?”

“Yeah,” I blushed, “Yeah, I do.” .

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