Column: Chasing those holiday shopping deadlines

In the holiday rankings, Thanksgiving always seems high atop any list. What’s not to love? Endless food, football games all day — and no pressure to buy any gifts. It’s a stress-free holiday (unless you’re in charge of the turkey, in which case, good luck). But if you’re heading to a relative’s house, bringing a pie or bottle of wine covers it.

It’s that moment Thanksgiving ends when the stress of the holiday season firmly sinks in. Every year, I like to believe I’ll get ahead of the game on Christmas shopping to spread out the inevitable burden that ensues. And instantly, it feels like I’m way behind. 

The calendar hasn’t even flipped to December yet, autumn leaves still cover the ground and I’m already feeling as if I missed out on all the great deals.

It’s as if the entire holiday shopping experience boils down to one extended weekend starting on Black Friday — otherwise, you risk paying full price for everything. The last thing anyone wants is to open that first credit card statement after Christmas and feel as if they’re doomed for the rest of the new year.

I’ve never experienced the full rush of Black Friday shopping (which, of course, actually begins on Thursday) by jumping on the early morning, or late night, spree. So right from the start, I’m always behind. That leaves Cyber Monday, which has now been around in earnest for about a decade, as my best option to secure some holiday deals. Even that can be overwhelming. It can be hard enough to figure out what to buy people. Even when you see something the person might enjoy, it’s hard to know if they already own it. Scrolling through pages of random items can feel hopeless at times.

Does anyone on my shopping list need a Snowflake Waffle Maker? It’s 20 percent off for the next 4 1/2 hours, the on-screen counter reminds me, ticking each second off. What about an 8-in-1 electric pressure cooker? The 22 percent off deal on Amazon is 32 percent claimed, with just over an hour left. Time’s running out, but I need to figure out how a pressure cooker works before I can decide if anyone might want one … 

Cyber Monday sales topped $1 billion in 2010 and reached a walloping high of $7.8 billion this year, according to the latest data released Tuesday by Adobe Analytics. Amazon, obviously, led the way, although a precise breakdown was not available. But the online retail giant did say it was the biggest day in its history. (Of course, that comes on the heels of the recent breakdown of all the tax breaks New York offered Amazon for its new headquarters in Long Island City. But that’s a topic for another day.)

The great deals extend beyond just Amazon and its many free shipping offers. Seemingly any and every online retailer offers some kind of Cyber Monday sale. My email is full of alerts from every retailer where I’ve ever made an online purchase, warning me of a looming sale end date.

60 percent off ends at midnight!

EXTENDED: 60% off + extra 15% off!

Ends Today: Up to 35% off!

By Wednesday, I might as well give up on holiday shopping and start preparing for Christmas 2019.

The holiday shopping experience was easier in my younger days, before I got into a serious relationship and then married. And my wife’s birthday is six days before Christmas, which adds another wrinkle into the experience. On top of Christmas gifts, I have to stay focused to make sure a birthday gift stands on its own and doesn’t feel like a Christmas add-on. The poor souls born around Christmas never like to feel gypped. 

Luckily, my wife is a great gift buyer, so I can always count on being on the receiving end of thoughtful presents. But, of course, that only adds the pressure; I need to nail all my gifts for her. And as we get older and spend more time together, it becomes increasingly difficult to think of things the other person needs.

I can barely come up with a list of things I would like, let alone ideas for other people.

I can usually count on a text from my mom in mid-November asking what I’d like for Christmas. My inevitable response is that I haven’t given it one second of thought yet. By Thanksgiving, she warns me that if I don’t act fast, I’m destined for all shirts under the tree as gifts.

Around the holidays, we’re always chasing a deadline.

The author is the editor of the Riverhead News-Review and The Suffolk Times. He can be reached at 631-354-8049 or [email protected].