Dating at Christmas? Oy to the World.

Dating is stressful, let’s face it. But dating during the holidays? Oy. Oh, so you’re casually dating someone while Christmas is getting ready to roll around? DOUBLE OY. Matter of fact, let me pour a glass of wine and let’s talk about that. Dating at Christmas, I think, is the HEIGHT of stress, causes the MOST aggravation and I imagine has most singing OY to the World rather than Joy to the World. Why is dating during Christmas so hard? Add the possibility of gifts to the mix and you have yourself a merry little…

Oy.

Now, you can TRY and calm your nerves by eating lots of chocolate and watching those sweet holiday rom-coms, with one caveat. Know you’ll see the Christmas Movie Version of dating during the holidays which always winds up 117 minutes later with the happy ending we all know and love. Which is usually something along the lines of the newly minted couple sharing that special gift which leads to that first magical kiss…

…aaaaaand scene.

But that isn’t real life!

Real life is a little more complicated than that.

Now, I might be an old married woman at this juncture, but I remember FULL WELL what it was like dating during the holidays. For me, worrying about Thanksgiving kicked off THAT stress-o-coaster in AUGUST with trying to decide if the person I was casually dating should be invited to dinner or was I going to have to schlep to some unfamiliar locale.

However, as soon as those leftovers were eaten up and December 1st rolled around, the question then wasn’t so much “where are we going to eat” but rather, “should I get a gift for the person I’m casually dating?”

And THAT, folks, is today’s sixty-four million dollar question, with a bonus million dollar question attached. Meaning, if you DO decide to get your casual beau a gift, WHAT THE HELL DO YOU GET THEM?

Fear not, my friend. Like I told you, I’ve got you covered.

Okay so, if you’ve gotten this far without taking a shot of tequila or hit the bong to assuage your holiday gift-giving-strategy stress in the making, I’m proud of you. Now take a deep breath because I’m about to make your life a whole lot easier by answering ALL your questions in the order that they were received.

So, should you get the person you’re casually dating a Christmas gift? Or Hanukkah Gift? Or Winter Festival Gift? Listen, I’m trying to cover all my bases here.

Anyway, I say if you feel like you want to go on ahead and get the person you’re casually dating a holiday gift, DO IT! And DON’T worry about if they’re giving YOU something or not. That’s not the point. I mean, you could always go the “no gifts” route, but what the hell fun is that?

After all, ’tis the season of GIVING, right? Now as for WHAT to get them, I suggest going the Secret Santa Route. Or I guess in your case, it’d be the NOT-So-Secret-Santa route, ha ha.

What do I mean? Think about it. If you’re casually dating someone, you’re probably about on the same par as knowing them as you would be, say, Mindy in Accounts Receivable, right? Well, maybe a LITTLE better. But you get my point. You don’t want to get your date something REAL expensive, because if it’s a situation-ship or a new maybe-this-could-be-a relationship, an over-the-top gift will NOT impress them. In fact, it’ll have the opposite effect; it will chase them away faster than a positive COVID test.

Like, you don’t want to pick them up that Apple watch, okay? You DO NOT want to be the one who when their parents see you, say “here comes your credit card.”

And now for the answer to question number two – WHAT TO GET THEM?

Want to know the secret to holiday gift giving while casually dating?

Here it is.

You want to get something somewhat impersonal, but PRACTICAL, and keep it around $25 or less. You know, like the Secret Santa exchange at work. Now, you might’ve picked up a few gift ideas from conversations with the person you’re dating. But if you’re ABSOLUTELY stumped and scrambling (in either a dating OR Secret Santa situation), here is a list of pretty awesome gifts you can get for someone you don’t know very well that I just bet will go over FAR better than say, a fruitcake.

And the best part?

ALL the gifts on that list are under $25 so your budget will NOT be broken! AND you don’t have to brave a mall during a pandemic!

How’s THAT for a hell of an idea?

Still not sure? Let me assure you I have perused this list myself and I think you’ll find the PERFECT gift. Now listen, if THAT list isn’t your jam or you want to spend less money, feel free to ask the Google for gifts under the amount of money you’re willing to spend, or if you’re crafty, make them something!

I mean, a plate of cookies goes a LONG way. Or write to me on Twitter, give me your details and their details and I’ll see what I can come up with as an idea. Feel free to hit me up at @archangelcrew – I’m always up for a gift-idea challenge.

And, look, if you’re worried even a TOKEN gift will chase them away than good damn riddance. After all, who doesn’t love receiving a gift, right? Especially something they can use and will make them think of your shiny happy face every time they use it? That’s a total win-win! But again, if you’re worried about it, but still want to get them a gift, keep this in mind – the more “token” a gift, the better. As long as it isn’t used, makes you look cheap, or is cash.

All that said, I would suggest NOT going the gift card route. You might THINK they’ll use it, but that Starbucks card you agonized over will most likely get shoved to the back of their wallet, never to be heard from again until next Christmas when they see it and regift it to their auntie in South Dakota.

So now let’s recap and see what we’ve learned, shall we?

Q. Should you get the person you’re casually dating a Christmas (or Hanukkah) gift?
A. Absolutely 100% a resounding YES!

Q. How much should you spend?
A. Under $25, ideally.

Q. Practical gift or personal gift?
A. Practical. ALWAYS practical for the casual dater, lest you look like a stage 5 clinger and/or stage 5 stalker. You don’t want them to wonder how you found out about their obsession for Baby Yoda when they never even told you they LIKED The Mandalorian.

So there you have it, folks! Stress no more about gift-giving, my casual holi-daters. Matter of fact, I’d bet my last piece of Christmas ribbon candy and last coin of Hanukkah Gelt that even the most casual of daters and frazzled of shoppers can follow these gift-giving tips and go from Oy to the World to Joy to the World in no time flat.

Happy gifting (and dating),
Meredith Silverman