The Gift That Keeps Giving: 7 Stages of Buying Someone a Drink This Holiday Season

When you’re single, the holidays can sometimes feel a little lonely. But hey, you’re not the only single person in New York City at Christmas. 

So when you’re out and make eyes with someone at the bar, you might want to break the ice by buying them a drink.

However, there are MANY ways to screw up what could (and should) be an easy way to strike up a friendly Christmas conversation with someone.

Although the holidays are basically a built-in segue to casually introduce yourself, this can work against you just as much as it can work for you.  

Play your Christmas cards right, and you could find yourself on a sleigh ride for two in no time.


1. Go somewhere you’re not a regular

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Part of what makes the holidays special is the hope it brings for something new and unexpected. Sticking to the corner pub a block from your apartment probably isn’t your best bet for finding something out of the ordinary.

So for starters, pick somewhere you’ve never been. Maybe there’s a spot you’re been wanting to try or somewhere you read about that sounded dope. People are usually extra warm and welcoming this time of year. It’s the perfect chance to venture out from the North Pole, even if for just one night. 


2. Don’t approach the first hot person that passes by

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It’s easy to get distracted by what the eyes can see, especially when surrounded by twinkling Christmas lights and shimmering garland in an already dimly-lit bar. But much like waiting for presents on Christmas Eve, it pays to be a bit patient.

Get a feel for the crowd. If someone catches your eye, assess the situation. Are they alone? Are they with friends? Are they already taken? Any of these simple observations can drastically change how you should approach that reindeer.


3. Do NOT use holiday pick-up lines

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No matter how clever, funny or charming you think your favorite Christmas pick-up line is, save it for your Twitter. No one wants a total stranger to come up to them and ask if they like "Jingle Bells" because they’d like to go all the way with them. No one.

Pick-up lines are a dicey business already, so adding some “holiday cheer” to them doesn’t do much but get you an extra hard eye roll. It may be true that good tidings aren’t the only thing you could give them tonight, but let them figure that out on their own. Unless it’s last call.


4. Offer them a Christmas-y drink

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If you’re going to buy someone a drink, why not offer them something they might not have chosen for themselves? It also opens the whole possibility of “trying something new.” (See? Now you can use a clever line like that!)

Check to see if the bar has a specialty holiday cocktails menu. Most will have at least two or three seasonal selections, and if they don’t, try for a peppermint martini, spiced cider, or a hot toddy. These are pretty common Christmas cocktails that can be made from year-round ingredients.

Pick two and keep those in your mind. Offering someone a specific choice rather than just asking to buy a drink shows you put thought into this before coming up to them. And if they don’t want any of those, they’ll say so and pick something else.

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5. Start with your name

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This seems like a simple suggestion, but you’d be surprised how many people don’t start off a new interaction with this like a normal human being. The holidays can be a crazy and stressful time and sometimes a small dose of normal is on the top of their wish list.

“Hi, I’m….” rolls off the tongue with much more effectiveness than any compliment on eyes, smile or what they’re wearing. No matter if it’s a guy or a girl, people like to be treated like a human, not a stocking waiting to be stuffed.


6. Use the holidays to your advantage

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Sometimes finding conversation can be tricky, especially when you know nothing about them. But everyone is affected by the holidays in NYC, even if they’re not celebrating them.

Chances are if you ask someone what they’re doing for the holidays, they have more than just a one word answer. And if they do give the “nothing” response, follow up with a “why not?” There’s probably a story there.

Whether it’s asking what’s on the top of their present wish list this year or complaining about the cold weather, use the commonly felt and known aspects of the season to keep the conversation snowballing.


7. Don’t be a Scrooge

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It’s the season of giving, after all. If you’re fire’s lit, and you hear the sugarplum fairies dancing around above you, pony up and get them another drink. This was your idea after all.

Budgets are tight on most people, especially around the holidays. Another act of generosity under the banner of “the spirit of Christmas” can only further help your cause. Be sure to learn from your ghosts of Christmas Past.

Many feel Christmas is the most magical time of year. So who knows? Try these and you might just find yourself sliding down a different chimney tonight.

Check out 8 Tips for Surviving Your Office Holiday Party

[Feature Image Courtesy Metro] 

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