The Pros and Cons of Proposing on Valentine’s Day

A man on his knees proposing to his girlfriend with red heart balloons in the background on Valentine's Day.

Valentine’s Day is known as the day you use red hearts, chalky box candy and giant teddy bears to show your significant other how much you love them. But some of you may be planning more than just a quick stop down the holiday aisle at your local drugstore. You may be planning something that has a little more sparkle than a Hallmark card and costs about two months of your income.

If you’re thinking of proposing to the love of your life on the official day of love, here’s some pros and cons to consider before channeling your inner Saint Valentine and asking that important question on February 14th.

Pro: It’s a Day of Love

Valentine’s Day is already a romantic holiday. Restaurants are decorated with red roses and candlelight, while stores are stocked with every heart decoration, chocolate, wine, and colored rose petal you can think of—giving you a jump start for the perfect ambiance.

Con: It’s Expected

Since Valentine’s Day is supposed to be the most romantic day of the year, your sweetheart might be expecting a marriage proposal. Maybe they started dropping hints to you that they are ready to be engaged or have been texting you pictures of diamond rings they love. This could have them on edge already, but once you start acting more affectionate, nervous, and keep checking your pocket, they might be tipped off to what’s going on. This may lead them to not be as surprised as you would hope when you get down on one knee. If you’re going for shock and a true surprise, you may not want to propose on Valentine’s Day.

Pro: You Can Make it a Weekend Getaway

A young man and woman having a romantic moment on Valentine's Day with lights in the background.

Why celebrate this romantic holiday for just one day when you can draw it out into a weekend? This is a perfect opportunity to ask your sweetheart to spend a weekend together, making your proposal plans that much more special. What could be any more romantic than whisking them away to celebrate the new step you’ve taken together?

Con: It’s Expensive

You may have caught an amazing deal over the holidays for a beautiful engagement ring, leaving some leftover money in the budget to plan a little something else for the proposal. However, you may find that the cabin you wanted to rent is priced higher on Valentine’s Day weekend—and those long stem red roses you know your partner will love are now more expensive than originally planned. If you’re over your budget and stressed out that you can’t afford to execute the proposal the way you wanted too, you may consider proposing on another day besides Valentine’s Day.

Pro: It Will Be Extra Memorable

A man on his knees proposing to his girlfriend as she's jumping in the snow on Valentine's Day.

30 years from now when you’re sitting around the kitchen table with your grandkids and they ask how you got engaged, you’re going to remember the date. You can look at their wondering eyes with confidence and tell them “It was Valentine’s Day…” before you begin the romantic tale. You can tell them how the snow was falling, or it was nice enough for a walk downtown, when all of a sudden you found yourself crying with happiness as you began a new chapter of life. Future February 14ths will hold a special meaning for your relationship and give you something else to celebrate: the day you decided to fully commit to one another.

Con: There Will Be Crowds

You might have a beautiful, perfect plan in your head of going to the spot where you had your first date to propose. However, you may find out that 12 different couples had the same idea and now your favorite little restaurant is packed and there is a line out the door. On record, Valentine’s Day is the second busiest day of the year to go out to eat. Think about the crowds before you get down on one knee, tripping a waiter with a tray full of spaghetti. (Not to mention, an even worse situation is if you hand over your ring to be put in a dessert, only to find out the kitchen has accidentally given you someone else’s ring in the hustle and bustle!) Think about where you plan to pop the question and how many people might have the same idea.

An important question to ask yourself is if your significant other even likes Valentine’s Day. Are they into the hearts, roses, and chocolate—or are they more of an “It’s a Hallmark holiday; let’s stay home and eat take-out” person? The best proposal plan is one you’re comfortable with and that your partner will love. Truly think about the person you’re asking before cupid’s arrow flies and you end up caught in the pressure and romance of the holiday.

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