A Guide to Your First Valentine's Day

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This post is not based off of one specific question or request but based off of several, recurring questions asked to our Editor-in-Chief this month.


So it’s your first Valentine’s Day.

You’re in a relationship for the first time. You’re dating someone in February for the first time. You’re seeing someone or you have a crush, and you’ve noticed that it’s the middle of February. Maybe you’re single but you’ve decided you want to embrace the holiday. Maybe you want to celebrate with friends. Whatever your situation, I’m here for you.

Honestly, I never thought I’d be anyone’s go-to for advice on anything like Valentine’s Day. I didn’t date until my mid-twenties and even then, I married the first man I dated. And then our first Valentine’s Day, I didn’t even manage to tell him that I wanted flowers because in some very early-day rant, I had told him that I hated the thought of men giving women flowers and then promptly forgot about it. I didn’t actually hate the thought of being given flowers, and I wanted them very badly. Before I met my husband, I was amazingly bitter on Valentine’s Day, rolling my eyes at the whole ordeal. Hardly anyone you’d want to ask anything about embracing the holiday. I’ve grown to love it since though. It’s a wonderful time to celebrate all the loved ones in your life, whether romantic, familial, or platonic, and it’s also a wonderful time to celebrate yourself and do whatever it is that makes you feel good.

Anyway, celebrating Valentine’s Day for the first time, no matter your circumstances, can be stressful. No matter how you look at it, it is a commercial holiday, and it’s been drilled into all of our heads that we need to go on elaborate dates and give nice gifts in order to celebrate it properly. And that, frankly, is bullshit. It’s what drives everyone’s edgy “Valentine’s Day is dumb” argument, and it’s fair enough. But Valentine’s Day isn’t dumb. Nothing that encourages us to express love and put a bit more happiness into the world is dumb.

So my tips for making the holiday as stress-free as possible:

  • Put Yourself First. Make sure you’re comfortable with every aspect of the day. If you’re single, do what you need to do to enjoy the day. If you’re seeing someone, establish your boundaries and make sure you aren’t pressured into doing something you aren’t comfortable with, at any level, which brings me to:

  • Communicate. Get in touch with your own feelings, but also communicate with your partner or your date. If you don’t want to go for an elaborate dinner date, say so. If you don’t want to give or receive flowers or gifts, say so. If you’re allergic to chocolate, make that clear. Let your partner know what you expect from the day and how you want to celebrate it, and listen to what your partner has to say as well. Valentine’s Day is only fun and only means something if you celebrate it in a way that you both enjoy.

  • Plan Something Together. Unless you like big surprises, Valentine’s doesn’t have to be about anything big or grand. Plan your celebration together, according to what’s right for both of you.

  • You Don’t Need to Spend Money!!!!! Valentine’s Day does not have to be about spending money. Make a card with what you have at home. Turn to magazines, old wrapping paper, and whatever inspires you. Bake something for yourself or with your partner! Make your favorite cookies together. Cook a nice dinner (together!).

  • Share Your Favorites. An easy hack with gifts or event planning at the beginning of a relationship is to share your favorites. Give your partner an edition of your favorite book (maybe even annotate it! or maybe even give them your own copy). Make them your favorite meal. Give them your favorite flowers. Take them to your favorite museum. I’ve introduced this as a hack, but it’s actually a great way to share what you love but also to open yourself up to new experiences with your favorites. Ask your partner to share, as well. If for instance, you’re cooking a favorite dish, ask them to make their favorite desert or their favorite drink. If you go to your favorite museum, ask them to bring you to their favorite café or restaurant afterwards. (And as a bonus, if either or both of you are anxious people, it’s also a source of comfort!)

  • Think of Alternatives. You don’t like to give cut flowers because they die, but you want to give flowers anyway? Give a potted plan as a sign of commitment, or a paper flower bookmark so your partner can carry it around everywhere with them.

  • No Pressure!! You don’t actually need to do anything for Valentine’s Day, so don’t let it be a source of stress or pressure. Only do what’s fun for both of you! Get takeout and stay in (likely what my husband and I are doing tomorrow), or go all out! Just enjoy yourself.

Finally, building on that last point, remember that it’s just a day and you may not even remember your first Valentine’s Day with someone. All I remember from my first Valentine’s Day with my husband was that it was stormy out and I was very in love with him and he totally quoted Chaucer in the card he wrote for me.

Relax and have fun!