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Ask Anna: How to handle being single during cuffing season without losing your mind

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 binging 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 hi 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 café 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.

TLDR: Being unattached gives you freedom—embrace it.

Don’t ignore the loneliness

Let’s be real: Even with all the fun activities and re-framing, loneliness happens. It’s normal and it’s okay. When it does, acknowledge it without judgment. After, try doing a short meditation, text/call a friend, journal about what you’re feeling, or treat yourself to a small comfort (hot cocoa, fuzzy socks, a short walk in the sun). You’re allowed to feel sad occasionally, but don’t let those feelings convince you that you’re broken or unlovable. You’re not.

Remember, this too shall pass

Cuffing season is temporary. (Hell, all seasons are.) And singledom often is, too. It might feel like everyone is coupled up, but even if many are, remember that relationships don’t magically solve life’s problems. Sure, those matching pajama pics on Instagram look cozy, but what you don’t see is the argument they had over why you have to buy your partner’s mom the perfect gift when she doesn’t even like you, the stress of coordinating whose family to visit, or the passive-aggressive tension at holiday dinners with your racist uncle.

Being single means you have the luxury of avoiding some of those struggles, at least for now. No in-law drama, no forced smiles during tense family events, and no coordinating your every plan around another person’s schedule. (Merry Christmas!)

So, sip your peppermint latte with abandon, throw on that Mariah playlist, and enjoy the freedom to make this season your own. You’re your own best present.

While relationships can be wonderful, they’re not an escape from life’s messiness. Everyone has their struggles. Focus on embracing where you are right now, because there’s value and growth to be found in every season of life.

Anna Pulley is a syndicated Tribune Content Agency columnist answering reader questions about love, sex and dating. Send your questions via email (anonymity guaranteed) to redeyedating@gmail.com, sign up for her infrequent (yet amazing) newsletter, or check out her books!

This column originally appeared on The Chicago Tribune.

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