Valentine’s Day—love it or hate it, there’s no denying it’s the most romantic day of the year. Red roses, candlelit dinners, heart-shaped chocolates, and a general air of love in the air. Naturally, for many people in love, this begs the question: “Is Valentine’s Day the perfect day to propose?” As a wedding celebrant, I’ve seen all kinds of love stories—some that start with surprise holiday proposals, and others that unfold in the most unexpected ways. If you’re thinking of proposing on February 14th, it’s worth weighing the pros and cons before you pop the question. Let’s dive in!
✅Pros: Why Valentine’s Day is a Great Day to Propose
Built-in Romance: The Setting is Already Perfect
Valentine’s Day is literally designed for love. Everywhere you look, you’ll find a romantic backdrop—restaurants with dim lighting, florists overflowing with roses, and love songs playing in every store. You don’t have to do much to set the mood because the day does it for you! A beautifully decorated dinner table, a walk under twinkling lights, or even a cozy night in with chocolates and a heartfelt speech—all these things feel extra romantic simply because of the date on the calendar. If your partner is a sucker for all things hearts and roses, this could be a dream come true!
It’s a Storybook Moment
When people hear “We got engaged on Valentine’s Day,” they instantly get the vibe—romantic, sentimental, and full of love. It’s the kind of story that doesn’t need extra explanation: “He proposed on Valentine’s Day!”—instant aww factor. If your partner loves grand, cinematic moments, proposing on February 14th gives you that fairy tale moment they may have always dreamed of.
Easy to Remember
Let’s be honest: some of us (cough, forgetful partners, cough) struggle to remember anniversaries. But February 14th? That’s an easy one. You’ll never have to worry about forgetting the day you got engaged because it’s forever linked with Valentine’s Day. And every year, when the holiday rolls around, you get to celebrate both your engagement anniversary and the day of love—double the romance!
Extra Celebration & Built-in Traditions
Engaging on Valentine’s Day means that every future Valentine’s Day has extra meaning. It becomes a day where you can not only celebrate love but also reminisce about that life-changing moment when one of you got down on one knee. Plus, you can start sweet traditions—maybe recreating the proposal dinner every year or reading love letters to each other. If you love the idea of having a meaningful day with extra sentimental value, this is a big plus!
❌ Cons: Why You Might Want to Rethink a Valentine’s Day Proposal
It’s… Expected 🎭
If your partner has a feeling you’re going to propose soon, Valentine’s Day might be the first date they suspect. Let’s be real—romantic people LOVE surprises. If they’re already half-expecting a ring when you book a fancy dinner, the element of surprise might not be there. If you know your partner loves to be caught off guard (in a good way!), a Valentine’s Day proposal may not be the best way to shock them in a good way.
Sharing the Spotlight (aka, You’re Not Alone)
Thousands (if not millions) of people around the world get engaged on Valentine’s Day. What does that mean? Your beautiful, once-in-a-lifetime moment might get lost in the sea of other proposals flooding social media.
📱 Instagram, Facebook, and TikTok? FULL of “We said YES!” posts.
🍾 Fancy restaurant? There’s a good chance another couple is getting engaged two tables over.
If you or your partner want a truly unique and standout engagement story, Valentine’s Day might feel too common for such a special milestone.
Everything is More Expensive 💰
Have you seen the price of flowers in February?! 🌹 Valentine’s Day is one of the most expensive days of the year to buy flowers, book a dinner reservation, or hire photographers.
If you’re planning a big, dramatic proposal (think: five-star dining, musicians, a private rooftop view), you’ll be paying premium prices for everything. Compare that to proposing on literally any other day—you could save hundreds, if not thousands, of dollars on a dreamy engagement experience without the Valentine’s Day markup.
Combo Holidays: Romantic or Redundant?
This is a tricky one. Some couples love combining special occasions (think Christmas proposals, birthday proposals, etc.). But others feel like it takes away from each celebration.
If you get engaged on February 14th, every Valentine’s Day becomes a double celebration—your engagement anniversary and the holiday. Some people love it. Others? Not so much. If your partner likes individual moments that stand on their own, consider proposing on a separate day to give your engagement its own identity outside of Valentine’s Day.
Final Verdict: Should You Propose on Valentine’s Day?
It depends on your partner! 💖 If they love all things traditional, romantic, and storybook-worthy, a Valentine’s Day proposal is PERFECT. They’ll love the sentiment, the built-in romance, and the beautiful anniversary date.
But if they prefer unique, unexpected moments, or if they like keeping big milestones separate from holidays, you might want to choose a different day for your big question.
Want the Best of Both Worlds?
Instead of proposing on Valentine’s Day, why not start the engagement process in a sweet way?
🌹 Slip a note into their Valentine’s card that hints at something big coming soon.
🍷 Plan a special dinner where you talk about your future—without giving it away just yet.
💍 Use the day as a decoy—act like it’s just another Valentine’s Day, then propose a few days later!
That way, you keep the romance but still get the surprise factor. Win-win!
