How to Win at Valentine’s Day (Even if You Think It Sucks)

And this may sting — sometimes that’s a Hallmark card.

You Can Date Better
5 min readFeb 7, 2023

We’re heading toward Valentine’s Day, and holy Cupid, what a holiday.

A lot of folks have feelings about this holiday —which is fitting, being that the holiday is about really big feelings.

Some of you are all boo’d up and feeling the pressure to perform, others are ready to pamper your fabulous single selves and ignore the couples hype. I know a handful of bakers are getting ready to pass out their thoughtfully designed treats to every person in sight (whether they want them or not), or you may have a long-standing vendetta with Hallmark’s earnings and this year… let’s burn it all down.

Even if you think you’re above it all and it’s meaningless for you, you still have to live in the world, and every store, media outlet, social sphere and event is tailored around the 14th of February’s Saint Valentine traditions.

Suck it up, it’s happening. (And yes, those candy hearts are still cute as heck but taste like chalky trash — SweeTARTs versions are better, just admit it!)

I am not here to tell you exactly how to celebrate this very innocuous love holiday. Do what serves you and makes you a happier (not more bitter) person the next day.

I will, however, offer a perspective that helps me — someone who loves a good calendar reminder and whose strength is not heavy sentimentality.

Valentine’s Day is just a reminder for me to check in about my expressions of love. Where can I use a little boost in my communication of positive feelings for others? It’s a gentle ask for me to do something I don’t normally do…like being the first person to say, “I love you,” in a given week.

Not that hard, you say? Psh. Let’s dig in.

If you’re familiar with the 5 Love Languages, it’s a very common framework we use with dating and relationships to model how we give and receive love. I use frameworks a lot in coaching and I always like to say — use the ones that speak to you and actually give you a place to move forward in terms of thoughts and behavior.

I like the 5 Love Languages framework because it’s so tangible. I can look at a period of time and literally break down how each of the 5 categories (Gifts, Quality Time, Words of Affirmation, Acts of Service, Touch) have played out that day, that week, or even throughout the year.

Here’s how Valentine’s Day serves me, specifically: I know I have different ways I like to give and receive love sometimes, and V-day is a time to look at that imbalance and do something different. It’s a way for me to grow and stretch — just a teeny, tiny little bit.

My significant other is a great example. Both of us appreciate touch, so that’s great. Yay, us. But here’s the thing — I fall short at giving him words-of-affirmation because I’m a heavy acts-of-service person. I joke that I’m a “high context” person, meaning I assume a lot about how we’re both doing based on the actions we perform for each other and if nothing has been said or done that explicitly changes anything — then nothing has changed. When feelings come up, I talk. Otherwise… we’re good, right?

I’m a do more, say the minimum person. My amazing partner, on the other hand, is all about the verbal expression. He could verbalize nice things all day but it’s not his first impulse to do an act of service to show it.

This love language imbalance issue is a common dynamic with relationships of any kind and guess what — you can work on it! So, that’s what I (try to) do. I see that V-day in the middle of my February calendar and think, how can I do something a little extra that’s out of my normal zone for showing love to someone? Or in my single days — for myself!

The same might be true for you. Maybe you know you’re lacking at putting aside quality time for your special people (or yourself). Make a date with no distractions!

Maybe you never think to get a little meaningful gift for someone that loves a little purchase once in a while (like yourself). Get that new kitchen gadget, woo-hoo!

Maybe you need to stare yourself right in the face and tell yourself that you love yourself a few times... and then go give that gift to someone else too. Gah, that feels good. Mmm, mm, mm.

V-day is a calendar reminder for us to work on this communication and what a day to do it. The great thing about this holiday is that it can be celebrated in all kinds of ways and hit all those love language pieces, however it works for you and your social network. Chocolate! Jewelry! Movies! Snuggles! Cooking a meal! Think about what someone (or everyone, hey, go big) might appreciate based on how they receive love and figure out how you can stretch yourself to communicate in their language.

My perspective is — just communicate in some way to your partner, your mom, your neighbor, yourself. Say it, or do it, or spend the time, or give the gift, or offer a snuggle... but try a different way or choose the language that others may need, not necessarily what usually comforts you.

And this may sting — sometimes that’s a Hallmark card.

Voilà. Valentine’s Day solved.

Change the way you date. Get a coach. Get dating.

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You Can Date Better

Writing/content curation by Carrie Prince, founder & boss lady behind — coaching & consulting for the current online dating landscape.