Ask Anna: How to handle being single during cuffing season without losing your mind
Published in Dating Advice
Dear Anna,
Usually Mariah Carey season is my favorite, but this year I’m struggling. Everywhere I look, people are cozying up, planning cute holiday dates and posting about their jolly AF lives. Meanwhile, I’m single, spending my evenings scrolling through dating apps and wondering if I should just settle for someone mediocre so I’m not alone through the holidays. I love my friends, but most of them are in relationships, so I feel like the odd one out. I know being single isn’t the end of the world, but it’s hard not to feel left out — or like I’m doing something wrong. How can I embrace this season without losing my mind (or my self-worth)? —Single, Or Losing Out?
Dear SOLO,
There’s a reason that cuffing season is known for sky-high depression rates, and loneliness is a big one. Social media doesn’t help this, nor does seeing all the cute Instagram couples in their matching flannel pajamas, or the Hallmark movies that make you feel like a failure for not seducing any hot, small-town bakers/widowers while saving their business (and Christmas).
First things first: You’re not doing anything wrong. Let’s just get that out of the way. Being single during the holidays isn’t a personality flaw; it’s a relationship status, and it doesn’t define your worth. At all.
That said, I get it — feeling like the third wheel on the gingerbread merry-go-round can be tough. But here’s the thing: the magic of the season doesn’t have to hinge on having a plus-one. There’s plenty you can do to make this time feel fulfilling, fun and even freeing. How? Let’s nog this dog.
Reframe the narrative
The holidays are marketed as a time for romance — to sell you things, let’s remember — but they’re also about connection, gratitude and celebration. Lean into the parts of the season that don’t require a partner. Plan a movie night with friends (ugly sweaters optional), volunteer at a local shelter or host a gift exchange. These moments will remind you that love isn’t limited to romance — it’s in your friendships, family and community.
Stop scrolling and start doing
If scrolling Insta and dating apps feels like punishment, give yourself permission to take a break. Dating doesn’t have to be a 24/7 project, and swiping while you’re feeling down can lead to further alienation, or worse — settling for someone who’s ... meh. Instead, focus on activities that actually make you happy. Always wanted to learn how to bake a strawberry rhubarb pie? Take a class. Interested in a pottery workshop or a pole-dancing class? Go for it. Bonus: You might meet people who share your interests, and at the very least, you’ll have something new to enjoy. (Or a slightly lopsided bowl to give to your mom instead of an impersonal gift card.)
Create a 'single season bucket list'
Rather than viewing this time as something to endure, treat it as an opportunity. Lots of us have time off around this time — now’s your chance to make the most of it. Make a list of things you can only do because you’re single. Travel solo, go to a party (or a bachata class or a speakeasy) and practice flirting with strangers, spend an entire Saturday binge-watching your favorite show (or book) without negotiating or feeling guilty, or throw a dirty cookie party where you reward the most outlandishly decorated vulvas and schlongs.
Other options are:
Have a “yes” day: Say yes to any opportunity or invitation that excites you, whether it's joining a Meetup group, K-pop karaoke, or saying hello to someone who catches your eye.
Treat yourself to a nice dinner — alone: Go to that restaurant you’ve been eyeing, dress in an outfit that makes you feel confident, and indulge.
Go on a dating experiment: Try a creative approach to dating, like going on three “adventure” dates in one week (think rock climbing, ice skating or exploring a holiday market). Make the activity the important thing, not who you’re with.
Binge-watch some single classics: Watch shows or movies that celebrate single life, like "Legally Blonde," "The First Wives Club" or "Barbie."
Create a vision board for the upcoming year: Envision what you want to accomplish in the next year — romantic goals optional.
Explore your city as a tourist: Visit a museum, check out holiday light displays or try a trendy cafe you’ve been meaning to visit.
Design a signature cocktail or mocktail: Experiment with mixology and create a drink that feels festive and you. If it turns out tasting like rubbing alcohol and cilantro, there’s no one around to judge you.
Write a love letter to yourself: Reflect on what you love about being you, everything you’re grateful for and what you’re most proud of. Save to reread when you need a confidence boost.
Test out new styles: Experiment with a look you’ve wanted to try — whether it’s a haircut or color, statement outfit or bold makeup.
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