How to Actually Enjoy Valentine’s Day Without the Overthinking

Ah, Valentine’s Day—the one holiday that seems specifically designed to trigger every overthinking, anxiously attached, people-pleasing millennial woman out there. Whether you're in a relationship, single, or “it’s complicated,” this day can bring up all kinds of feelings (none of which are covered in those pastel candy hearts).

If you’re already spiraling about what to do, what to buy, or how to make sure no one is disappointed—take a deep breath. You’re not alone, and you don’t have to let February 14th turn into an emotional marathon.

If you have people-pleasing tendencies, this holiday can feel less about love and more like a high-stakes performance review on how “good” you are at relationships. Cue the anxious thoughts:

💭 “What if my gift isn’t thoughtful enough?”

💭 “Are they expecting something big? Should I be doing more?”

💭 “What if they don’t like my plans? Will they be disappointed?”

💭 “Am I a bad partner if I secretly don’t care about this holiday?”

And if you’re single, it’s a whole other minefield:

💭 “Should I be sad? Am I sad? Do I need to plan a ‘self-love’ night?”

💭 “Are all my friends going to be busy with their partners?”

💭 “Should I post something cute or pretend this day doesn’t exist?”

If any of this sounds familiar, you’re not alone. Valentine’s Day can bring up a lot of pressure—to be the perfect partner, to plan the perfect date, or to react in the perfect way to whatever your partner does (or doesn’t) do. And if you’re single, it can stir up feelings of being “not enough” just as you are.

But here’s the truth: You don’t have to let Valentine’s Day hijack your nervous system. With a little self-awareness and some intentional shifts, you can reclaim this day in a way that actually feels good to you.

1. Drop the Expectation Olympics

People-pleasers often feel responsible for making Valentine’s Day “perfect” for their partner, friends, or even family. But here’s a little secret: perfection isn’t the goal, connection is.

Instead of overthinking the exact right way to celebrate, ask yourself:

• What would actually feel enjoyable for me?

• Am I planning this out of love or out of fear of disappointing someone?

• Would I still do this if I knew they weren’t expecting anything?

  
  

There’s a lot of pressure to make this one day special, but let’s be real: romance isn’t about a single date on the calendar. Your worth isn’t measured by whether or not you pulled off the perfect Valentine’s Day. It’s okay to keep things simple, say no to things you don’t want to do, or even gasp skip it altogether.

2. Your Worth Isn’t Measured in Gifts (or Instagram Posts)

It’s easy to spiral into comparison mode when social media is flooded with extravagant date nights, elaborate surprises, and couple photos captioned #blessed. But remember: social media is a highlight reel, not real life.

A lack of grand gestures does not mean your relationship is lacking, and being single doesn’t mean you’re missing out. Your worth isn’t defined by how much someone spends on you, how public their love is, or how many flowers show up at your door.

3. Single? Celebrate YOU Instead

Valentine’s Day isn’t just for couples—it’s a day to celebrate love in all its forms, including self-love. If you’re single, instead of focusing on what’s missing, think about what would make you feel good:

• A cosy night in with your favourite comfort food and a nostalgic rom-com.

• A solo date to that café you’ve been meaning to try.

• A friend-date with your favourite people (Galentine’s, anyone?).

• A total social media detox to avoid the pressure altogether.

  
  

Loving yourself isn’t an if no one else does it, I guess I will situation. It’s an active choice to show up for yourself, not just today, but every day.

4. Communicate What You Actually Want

If you have a partner, don’t fall into the trap of hoping they’ll magically read your mind. If certain things matter to you—whether it’s a handwritten note or skipping the holiday altogether—talk about it.

Your needs aren’t too much or too demanding just because you voiced them. And if your partner doesn’t meet them in the exact way you envisioned? That doesn’t mean they don’t care. Give them the chance to show up for you in their own way.

5. Be Kind to Yourself

If Valentine’s Day stirs up hard emotions—loneliness, anxiety, comparison—it’s okay to feel that way. Instead of judging yourself for it, try offering yourself the same kindness you would give a friend.

• Remind yourself that your worth isn’t up for debate.

• Do something small that brings you comfort.

• Take a break from social media if it’s making you spiral.

  
  

Focus on what is in your control—like how you choose to care for yourself today.

Final Thoughts

Valentine’s Day is just one day out of the year. It doesn’t define your relationship status, your self-worth, or your value as a person. Whether you’re celebrating with a partner, friends, or just yourself, let this be the year you drop the pressure and embrace what actually feels right for you.

You deserve love—on Valentine’s Day and every day.

Happy Valentine’s Day (or just, happy regular day with extra chocolate opportunities)! 🍫