Top 10: Winning Christmas

I have been obsessed with all-things Christmas for as long as I can remember. Always favoring traditional white twinkle lights; I watch with wide eyes and welling tears each year.

This overwhelming, old-soul connection to Christmas has oftentimes felt as though I was destined to play A Christmas Carol’s ghost of Awkward-Youth-Past.

I would take a day off of school every winter, committed to transforming my family home into the best wonderland I could imagine. I’d immediately cash any checks from extended family and exchange them to buy small gifts, and even more decor. It never amounted to much, but it was one of the few things that made me tremendously happy.

So, it should be of no surprise that I continue to expand on this each year. Whether it be decorating a month “early”, abusing my neighbors’ quiet hours in favor of Hanson’s Snowed In, or showering my loved ones in thoughtful gifts – it’s become a whole plot thing (lookin’ at you, my Man Who Knew Too Little fans).

Friends, families, and lovers alike have crowned me “Queen Gift-Giver”. I’m here to share my talents for spreading Christmas cheer in the year where we can use it most.

Let me be clear, I wholeheartedly agree there’s no “winning” Christmas. Competitive and materialistic natures are guaranteed to suck the living joy out of any holiday gathering. Karen isn’t invited.

The following Top 10 tips aim to assist you in gifting thoughtfully and in getting more joy out of the process. Note: Most effective if read with hot chocolate in hand.

1. Solve a problem. If you’re buying a sizable gift for a significant other or family member, consider the potential impact of your generosity. It’s likely they are forgoing some of their own needs in exchange for others’ during the holidays. If you are able to offer any relief, your gift will be doubly appreciated. Don’t overthink it, simply evaluate recent frustrations they’ve shared; running shoes are worn down, make-up brushes are aged-out, or they’ve been needing a massage.

2. Personalize it. This tip can make even the most practical gifts feel indulgent. Consider if the gift can be monogrammed, artfully customized, or engraved. Note: this one is the “cherry on top” of an already great gift. An engraved ruler is still a ruler.

3. Consider quantity. We all know there’s some inherent child-like excitement involved in opening multiple gifts. But, it’s also great for the gifter. Not only does this allow an opportunity to take creative risks, it also relieves pressure off the success of the main gift. As a general rule, follow a 60%, 30%, 10% allocation for three total gifts.

4. Browse specialized gift shops. Google isn’t your friend. Go straight to the source. What bourbon do they like? What painting is their favorite? What college did they go to? Head straight on down to the distillery, museum, or university gift shop. You’ll find gifts they never knew they wanted. It’s the extra effort for me.

5. Make it a shopping event. Don’t register Christmas shopping as a dreaded to-do. Make it fun. Take a day to yourself. Buy your favorite coffee, arm yourself with an organized list, and turn up the radio. Relieve pressure by starting weeks in advance.

6. Release your ego. Don’t worry so much about how they’ll receive it. It’s free for them, and should be fun for you. It’s ok to be quirky. If you’re leaning on their interests and/or your shared memories, you can’t go wrong.

7. Share an experience. Hotel stays are incredibly romantic (unless you’re Tom Segura). Puzzles are quarantine approved. Board games are entirely underrated. There’s nothing quite like saying “I love you and I want to spend more time with you.” A mancala board can offer hours of bonding with a child. Monikers will keep adults laughing ‘til morning.

8. Celebrate the presentation. Similar to all steps above; extravagance unnecessary, thoughtfulness required. Whether a classic kraft wrap, a glittery landscape, or something ironic – this finishing touch sends a clear message: I’m proud of this. Note: Pay attention while they’re opening the gifts. Share in their excitement.

9. Match the “right” sentiment. If they mean a lot to you, stay away from the any-old-check-out aisle gifts that can send a different message. If you’re buying a gift solely in interest of reciprocity, stay away from the gifts that may indicate you feel more. Don’t buy jewelry for a woman you don’t love. Don’t buy an alarm clock for one you do.

10. Manage your energy wisely. Out of their own limitations or insecurities, some people may not enjoy receiving gifts as much as you love giving them. They may say something to slight you. Don’t dwell on their disheartening reactions, and remember to spend that energy elsewhere next year. No need to take it personal.

P.S. Click here to blast Kacey Musgraves’ flawless Christmas album while browsing the gift ideas below.

RBG Ornament, $

Great Gatsby Print, $

Rainy Day in Paris Umbrella, $

Etched Urban Glasses, $

Blanton’s Old Fashioned Gift Set, $$

Lush Sleepy Lotion, $

Kacey Musgraves Candle, $$

Four Seasons Bath Robe, $$$


“My idea of Christmas, whether old-fashioned or modern, is very simple: loving others. Come to think of it, why do we have to wait for Christmas to do that?”

Bob Hope


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