How to take the pressure off this Valentine’s Day

Top tips from our experts
By Paired
on March 24, 2025
Read time: 5 mins

Ever had a Valentine’s Day fail? Don’t worry, all the best couples have. When expectations are so sky high, there’s a huge number of things that could go very wrong. 

And when we surveyed Paired couples, it turns out they do go wrong, more often than you would think. But that’s all part of the magic. At Paired, we celebrate the real, imperfect moments that truly define your relationship. After all, it’s the little mishaps that often become the most memorable chapters of your journey together. 

So, in the spirit of taking the pressure off this Valentines, here are some real stories of where Valentine’s Day hasn’t exactly gone to plan:

1
“I got asked to start being exclusive on
a hot air balloon and passed out from being scared of heights.
Total disaster.”
2
“I had forgotten the date, came home to rose petals up the stairs, and had to sneak out the door and run to Walgreens to get a card. He never realized!”
3
“My husband decided to make me a three course steak dinner at home. He burnt the steak and forgot the asparagus. We ended up having milkshakes for dinner instead and laughed A LOT.”
4
“One year, life had been so busy that we got to Valentine’s night and both looked at each other with a look of worry. Neither one of us had planned anything! We ended up ordering Chinese take out and it was one of the most memorable Valentines ever!”
5
“We went skiing together for Valentine’s day weekend and decided to try snowboarding for the first time on day one. We both ended up being black and blue for the rest of the weekend.”
6
“He made reservations to
a pricey fancy restaurant that was inside an old docked ship. A special expensive menu, like gold foil cheese/fruit plates. That was that night he learned I'm more of a chicken wings and fries
kind of girl.”

Got some of your own stories to share? DM us on Instagram @pairedapp. We’d love to hear them. 

Aligning Expectations

At Paired, we’re all about turning the spotlight on honest communication rather than idealized romance. Our ‘What’s in Your Heart? Your Valentine’s Vision’ Question Pack has been carefully crafted by our Head of Relationships, Aly Bullock, a marriage and family therapist, to help you bypass the guesswork and openly share your expectations for Valentine’s Day. 

With eight thought-provoking questions, the pack is designed to:

1
Enhance Communication: Encourage candid conversations about what truly matters.
2
Align Expectations: Ensure both partners are on the same page about what Valentine’s Day looks like for them.
3
Strengthen Bonds: Build trust and deepen emotional intimacy through open dialogue.

A Different Kind of Gift

“Valentine’s Day has the potential to reinvigorate your relationship if you approach it with honest, open communication,” says Aly. “When couples share their expectations, it becomes clear that you don’t have to buy extravagant gifts or spend money to give your partner what they really want, the feeling of being loved and known.” 

Our Valentine’s Vision Question Pack is a gentle reminder that the magic of your connection isn’t confined to an idealized day—it lives in every shared smile, every mishap turned laugh, and every moment of understanding.

You and your partner can work through these eight questions at your own pace—whether on a cozy evening in or during a weekend getaway. The prompts create a safe space for authentic connection, enabling you both to express your hopes, avoid misaligned expectations, and ultimately enjoy every day as a true celebration of your love.

Embracing Every Day

So this Valentine’s Day, if your plans go awry, remember that it’s all part of the beautiful, imperfect journey you’re on together. With our Question Pack, you can confidently align your expectations, communicate openly, and celebrate (or not celebrate) this Valentines in your own way. 

Follow @pairedapp on Instagram to get the tea on what really goes down, and what couples really want this Valentine’s Day. 

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