Katherine Plumhoff
February 05, 2020 4:12 pm
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Last year was my first Valentine’s Day with a partner, and it was a disaster.

Decades of watching Nora Ephron movies and never receiving candy grams in middle school hadn’t eroded my usual Hallmark-holidays-aren’t-real stance, but neither I nor my boyfriend realized that until it was too late.

I’m much more pragmatic than romantic, and I didn’t think I cared about going on a Valentine’s Day date. My boyfriend often showers me with love and romance on a regular basis—sending flowers to my hostels when I travel without him and writing me love songs—so why did our plans for one hyped-up holiday matter? For Valentine’s Day, I told my partner I’d plan a casual date for us: an outdoor screening of A Star Is Born. I thought it was a great idea at the time, but telling him I’d bought the tickets was the beginning and end of our conversation about Valentine’s Day and of me thinking about it. 

But as I look back, my boyfriend and I had unwittingly made two mistakes, per two relationship experts. My first miss? Not actually asking myself what I wanted.

If I had thought about it, I would’ve realized that I wanted to be wooed, as silly as I feel admitting it.

Our second mistake was not talking about the holiday in a serious way. I hadn’t thought about what I wanted, let alone what my boyfriend wanted, and neither of us had thought to ask the other. Suzie Pileggi Pawelski and James O. Pawelski, authors of Happy Together: Using the Science of Positive Psychology to Build Love That Lasts, explain why that was problematic:

Because we didn’t communicate well with ourselves or each other about what we wanted, my partner and I had an unpleasant Valentine’s Day celebration. We were both confused and upset when I got quiet on the way home from the movie, and we had to go through the painful process of unpacking my feelings after the fact. I came to the realization that I wanted chocolates and poetry (though I was and still am very anti tacky stuffed animals and clunky a-kiss-begins-with-Kay jewelry), and my boyfriend acknowledged that he hadn’t considered it was my first-ever booed-up Valentine’s Day and that it should be made special.

To avoid making our mistakes, ask yourself what you want to do for Valentine’s Day, talk to your partner about it, and try these expert-backed suggestions to make that conversation go as smoothly as possible:

How to talk about Valentine’s Day with your partner

1Have a conversation about love languages and values.

Relationship therapist Layla Ashley says, “I would recommend bringing up the subject [of Valentine’s Day] in a conversation about traditions, values and love languages. It’s easier to talk about a sensitive subject before it happens rather than after you feel hurt. Start by asking your partner how they like to handle special holidays and anniversaries. And listen and understand before expressing your own preferences. Keep [the conversation] light and positive, and discuss what you like and love rather than telling horrible stories about past disappointments. You want to inspire your partner, not threaten them into submission.”

And if you’re not sure what your love languages are, marriage and family therapist Julie Ingenohl suggests researching them together.

“Unmet expectations equal disappointment, every damn time, and gifts are not the only way to give and receive love. According to Gary Chapman, author of The Five Love Languages, there are four [other love languages to consider]: acts of service, words of affirmation, physical touch, and quality time,” she says. “Planning your Valentine’s Day is a wonderful opportunity to have a discussion on which is your primary love language (there’s even an online quiz to figure that out) and talk about ways in which your partner already shows this.”

2Be direct, but don’t take yourself too seriously.

You don’t need to slyly work Valentine’s Day plans into conversations, says Dr. Nancy Irwin, a clinical psychologist and primary therapist at Seasons in Malibu. “Ask very directly, but with a sense of humor or levity,” she says, offering an example: “‘So, [partner’s name], are you one of those people who wants an over-the-top celebration [for] Valentine’s Day, or do you prefer simple and authentic? Or [should we] boycott the whole damned thing?’”

3 Get specific: Share ideas and make a plan.

Let’s say you and your partner have decided on the general theme of what the two of you want to do–a big celebration, a casual night in, or anything in between. What would make you both happiest within that plan? 

Taylor Mead, senior editor of Swoon, the Odyssey’s love and dating site, suggests brainstorming together:

Her advice for go-to Valentine’s gift for relationships of all stages is a shared experience. “It could be a concert you’ve both been wanting to go to, a comedy show you two have been dying to see, or a weekend getaway. For new couples, it takes the pressure off of ‘What are we, exactly?’ and puts the emphasis on the fact you enjoy spending time together. And for couples who’ve been together for a while, it gives you more quality time doing something new instead of going out to dinner for the 917 millionth time,” she says.

4Don’t compare your plans to anyone else’s.

We know that social media can be addictive and anxiety-producing. Its highlight-reel status invites can make us question our own lives, and even more so on big holidays where everyone’s feeds and stories are filled with beautifully-staged photos, smiles, and outpourings of love. 

Genesis Games, a couples’ therapist and owner of The Miami Therapist reminds us, “Your Valentine’s Day does not have to look like anyone else’s on social media.”

And that goes for real-life comparisons, too. Your roommate can do a six-course meal for their boo and you and your partner can decide to order copious amounts of takeout; neither plan is necessarily better or more romantic than the other.

5Compromise in the direction of the person who cares more about the holiday.

“There are no rules when it comes to relationships; each one is unique. But the general guideline is that if one of you is particularly invested in this day, the other should go along with it,” says Adina Mahalli, relationship expert at Maple Holistics. If Valentine’s Day isn’t your thing, but your partner is all about it, let them have their day. By being generous and flexible to make them feel loved when and how they like, they’ll be inspired to do the same for you.

And for me? Well, for my second coupled-up Valentine’s Day, I’ve leaned into being extra-communicative about my V-day expectations, and it already feels way better than sitting back and expecting everything to work out exactly as it would in a ’90s rom-com. And the same should go for your Valentine’s Day celebration, whatever form it takes. This day should be about two people and two people only: you and your partner. Enjoy your day without comparing it to what everyone else is doing—trust me, it’s worth it. 

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