The Ultimate Guide to Valentine’s Day 2024

Valentine’s Day: What, When, and Why

 

When we hear Valentine’s Day: we automatically think of roses, chocolates, and giant stuffed teddy bears clogging up the checkout lanes at Walgreen’s. But where did Valentine’s Day come from? What makes people think someone would want or need a giant stuffed teddy bear as a gift outside of a fair? Why don’t we get the day off from work?

Great question. We totally should.

What Is Valentine’s Day?

 

A better way to answer that is to say, “What is Valentine’s Day today?” Valentine’s Day, as we currently celebrate it, is a non-public holiday centered around the celebration of love. This celebration is performed through the exchange of gifts or cards and also by splurging on expensive Valentine’s tasting menus at high end restaurants.

While Valentine’s Day celebrates all facets of love, from platonic to familial, from conventional to unconventional, it predominantly focuses on romantic love and feelings of attraction. Valentine’s Day is all about the “Valentine:” a nickname you and your significant other only use once a year in combination with tokens of your love (like chocolate) to make each other feel special and loved.

While for most adults, being a Valentine is a sweet way of recognizing the joy and wonder of romance. in High School, people only get as crazy and paranoid as they do when they’re searching (or waiting) for a Valentine when it’s time for finding a date to prom. So here’s a quick shout-out to High Schoolers: Do. Not. Panic. You don’t need a Valentine to be a person. You’re awesome as is.

But where did this showering of love and gifts come from? Why is it that Valentine’s Day is the most romantic holiday in the world?

Valentine’s Day History

 

Way back in Ancient Rome (around 269 AD,) a priest named Valentinus was martyred by the Roman Emperor. Fun fact: No one actually knows why exactly. They aren’t even sure how many different Christian martyrs named Valentinus there were. Some claim there were three of them with the same name.

Some of these legends suggest that Valentinus was caught secretly marrying Christian couples—in defiance of the Roman Emperor—while others suggest that Valentinus was simply executed for trying (unsuccessfully) to convert the Roman Emperor Claudius to Christianity.

Nothing is entirely certain, except that he was executed on February 14th. Centuries later, he was deemed a Saint by Pope Gelasius, with his feast day fixed on his death. His feast day: St. Valentine’s Day.

I know what you’re thinking. Where’s the connection between an execution and romance? It’s a mystery. There’s one theory that there simply is no connection. It could simply be a coincidence. The one shred of evidence we have is that the English poet Chaucer first associated Valentine’s Day with the date that birds begin their courtship, heralding spring in 1382.

While we can’t know for sure why Chaucer chose this day, his poetry marks the first connection between romance, Valentine’s Day, and poetry (a critical development) in history.

In the centuries after Chaucer, poetry connecting Valentine’s Day and romance bloomed. By 1797, a British publication had released The Young Man’s Valentine’s Writer, a publication of pre-written romantic verse, suggesting that Valentine’s Day poetry was a serious business. So serious, in fact, that a young man would consider buying pre-written poetry for his Valentine rather than be caught with no poetry at all.

From there, it only took 120 years for Hallmark to release their first Valentine’s Day cards. Today, Americans send over 1 billion of these cards every Valentine’s Day. 1 billion! That’s more than three per American (go figure)!

When Is Valentine’s Day?

 

February 14th. Every Year. Do Not Forget. It’s kind of impossible to forget as it is automatically written on your calendar as a national holiday. To save yourself grief, you can set a reminder a month or so in advance if you want to get something out of the ordinary for your partner.

Why Don’t We Get Valentine’s Day Off From Work?

 

We 100% should. And St. Patrick’s Day. And Halloween. Hallmark, please use your power for good.

Valentine’s Day Cards

 

Every year, Americans send over 1 billion Valentine’s Day cards. It’s a serious business — expressing your love and all! Let’s be honest, though, store bought cards are 95% cookie-cutter stuff that’ll impress no one. Not even your dog. So if you’re already committed to the idea of going full Valentine this year, you should consider writing your own card. With your own, really personal message. How, you may ask. By taking the time to think through not only what you want to express but also how you’d like to do it.

Who knows? 700 years from now, history books may use your poem as an example of 21st century love poetry. You wouldn’t want those history students laughing too hard at you. Would you?

What to Write in a Valentine’s Card

 

The most important thing to do in a Valentine’s Day Card is to speak from the heart. Be honest with your feelings and be honest with your tone. If you’re not the type to rattle off lines of rhyming iambic pentameter, then don’t try to do so now. Now’s not the time to come across as forced.

Instead, you should focus on what your Valentine (or your sweetheart) means to you. It can be funny, it can be silly, it can be romantic—honestly, it can be anything as long as it is true to you and your relationship with your Valentine.

That second part is what can make the card a little tricky — you need to be respectful of the relationship you have with your Valentine. When writing, put yourself in the shoes of your Valentine, and make sure you ask yourself, “how would my Valentine feel reading this?”

Make sure to write from the heart! All good Valentine’s cards come from the heart. At the end of the day, if your card means nothing to others (other than that it’s cute/funny/heartwarming), but everything to your partner, you did it!

Funny Valentine’s Cards

 

So, you’ve decided you want to be funny! Are you funny? Well, are you? Now that you’ve second-guessed yourself into nausea, let’s get crackin’.

When writing a funny Valentine, the humor should not only show that you’re funny, but reflect the way you’re funny with each other. A humor only the two of you understand, perhaps, or an inside joke, a favorite terrible movie, or a memory that cracky you both up every time.

At its best, humor is disarming: it breaks down the walls that we build up in our psyches and allows us to relax and feel emotions we might typically avoid. Keep the humor light, crisp, and sentimental.

A friendly tip: Avoid poop or fart jokes, unless that’s really you and your sweetheart’s jam. In that case, please don’t share that with the rest of the world.

The same may be said for sex jokes. Unless you really, really know your partner and know they’ll get a laugh out of it, it’s best to save your “man from Nantucket” ribaldry for another day.

Cheesy Valentine’s Cards

 

What’s the difference between funny and cheesy? You can’t eat funny. Yikes. Sorry. I promise I won’t quit my day job.

Here’s a more technical, and accurate, definition: Cheesy (adjective): excessively exaggerated, cliche, overly dramatic.

Cheesy can be a safe bet because it’s Valentine’s Day. By this, I mean that since people already expect the exchange of romantic affection, the notion that the whole thing may be a little inauthentic is not too far-fetched. It’s not spontaneous; it’s without cause relative to your relationship; it’s performative. As such, a little cheesiness isn’t the worst thing in the world. In fact, it can often take a lot of stress and anxiety out of trying to write a Valentine’s Card.

But can it be cheesy and about cheese?

How can I summon the courage to express my love for you? Ciabatta is bread; gorgonzola is bleu… I’m provalonely without you. Brie mine

You can have those for free, you’re wlcome.

Printable Valentine’s Cards

 

If you have a doctor’s handwriting, but still want to impress with a handcrafted card, you don’t have to practice your cursive for days on end. There are tons of Valentine’s Day Card templates that you can download, customize, print out, and have delivered.

This way, you can type out that nice note instead of scrawling it. Notice that I’m typing this guide. If it were handwritten, I’d have been fired. And you know by now that I don’t have a career in comedy lined up.

Save your Valentine’s eyesight; print a card!

Valentine’s Day Cards for School

 

Valentine’s Day at school can be tricky!

In elementary school, it’s a safe bet to get everyone in the class a small card, along with a piece of candy. You never want to be the kid who doesn’t give candy.

By middle school and high school, the rules have changed. Typically, in these grades, students are more selective about who to give Valentine’s Day cards to. Instead of giving them out to every classmate, it is a mixture of handing out fun ones to friends, sprinkled in with (gasp) some bold stabs at giving a heartfelt card to that special someone.

It can be a tricky minefield to navigate; at that age, it often feels like a game to figure out if two people like each other, and no one wants to expose their feelings for fear of being rejected.

As a result, there is often an explosion of “secret admirer” Valentine’s Cards at this age. I can’t condemn or condone this behavior. Instead, I’ll reiterate what I said earlier: be respectful, thoughtful, and truthful. With that in mind, it can be a nice thing to get a card from a secret admirer as well.

Valentine’s Day Quotes

 

Not sure about what to say on your perfect Valentine’s Day Card? You don’t have to reinvent the wheel, we’ll give you some pointers. Whether you’re looking for funny V-day quotes or perhaps just a cute little way to say “I love you,” we are here for you!

Happy Valentine’s Day Quotes

 

• There is no remedy for love but to love more — Henry David Thoreau
• Love is composed of a single soul inhabiting two bodies — Aristotle
• I know of only one duty, and that is to love — Albert Camus

Funny Valentine’s Day Quotes

 

• Without Valentine’s Day, February would be … well, January — Jim Gaffigan
• All you need is love. But a little chocolate now and then doesn’t hurt — Charles M. Schulz
• Brie mine. C’mon! It’s a classic! I’m giving it away for free!

Do check out our list containing the funniest Valentine's Day cards to pair with these quotes.

Cute Valentine’s Day Quotes

 

• Love is being stupid together — Paul Valery
• Love is a friendship that has caught fire — Ann Landers
• The best thing to hold onto in life is each other — Audrey Hepburn

Valentine’s Day eCards vs. Printable Valentine Cards

 

It‘s a fight for the ages: eCards vs. printable Valentine cards. While an eCard is free and doesn’t impact the environment, it also really lacks flair. Unless your significant other is really into saving the environment, you’re better off with a printable card.. The issue being that eCards sort of seem like a last resort, as you don’t have to put any real effort into them. People appreciate a real card. If you have time to print it out and deliver it, do so. It is a much more thoughtful and authentic expression of love.

If the last resort is all you have, an eCard is still more than nothing at all. Your significant other may think you send the eCard because you forgot to send a card in time, though. Either way, if you’ve chosen the eCard, compensate by going the extra mile with a quality gift or romantic date, just to be safe.

Things to Do on Valentine’s Day

 

What to do? What to do? It’s the middle of winter when the sun hides for what feels like 17 hours a day, and you somehow have to make this romantic?

Not to worry—the key is focusing on your relationship. And the cold weather is great for cuddling—for warmth, of course.

Valentine’s Day has a bad habit of forcing its expectations onto the relationship. You have to get a dozen roses because that’s what you do. Not so fast! What you should do is what you and your partner want to do. It’s about celebrating your relationship and showing them how much you care. There’s no one size fits all approach to Valentine’s Day, however much flower shops are trying to tell you so.

Thinking about getting a giant teddy bear in the Duane Reade? Will your Valentine actually like that? If the answer is, “well, they have a collection of stuffed animals that suffocates me every time I spend the night,” then yeah! Go get that bear, you’re golden. In any other realistic case: Say “no” to the bear.

But what about dates? What activities and what places are worth going to? Again, it depends on your relationship.

If you’re the fine dining type, you can’t go wrong with a nice restaurant, though there are some caveats, so I guess you can go wrong. Sorry. First: restaurants fill up for Valentine’s Day quickly, so get that reservation in early—at least two weeks ahead of time. Second: restaurants often roll out special tasting menus. Sometimes these are a neat way to try a variety of fun foods in an intimate setting, but they’re also a way for the restaurants to make big bucks just because it’s February 14. On top of that, restaurants often churn people in and out quickly because of the high demand for reservations. If the idea of a crowded, overpriced night out doesn’t sound appealing, why not make dinner at home? Keep it nice and intimate. If you’re not the cooking type, even better. That makes it special. Just stick to the recipe, you’ll be fine!

Movies? Movies can be fun, but I hesitate to suggest them if it’s your first date. Why? You can’t talk during movies. It’s a silent affair. It’s less of a date than a showing that two people experience separately. Of course, after the movie you have time to talk. About the movie. So that’s sort of unromatic.

If you’re looking to elevate your movie game, consider going to a live performance. Theatre, symphony, ballet, and opera provide that same level of tender escapism while also making the evening feel special. Plus, you get a chance to dress up. Nobody dresses up for the local AMC.

Other great Valentine’s Day date ideas could be going to a museum, seeing a local attraction (though New Yorkers should, skip the Empire State Building—you’ll be in line for hours in the arctic chill), or going for a stroll in a park. It doesn’t have to be over-the-top, it just has to be thoughtful.

“That’s great,” you say, “only one problem: I don’t have a date.” Cool, cool — good to know. Ok, let’s get you one.

How to Ask a Girl out on Valentine’s Day

 

So, you’ve decided to ask a girl out on Valentine’s Day. I’ll be honest: last minute ask-outs are not my wheelhouse, but I’m going to give this my best shot.

First: it depends on whether you know the person already. If you’re simply looking for a, ahem, companion on Valentine’s Day, there are plenty of singles mixers on Valentine’s Day for folks in your exact situation. Otherwise, bars are a perennial option. Hey, I know plenty of happily married couples who met at a bar. It’s the real-life Tinder.

But let’s say that you know the person. She’s an acquaintance. You’ve found out she’s single and has no Valentine’s Day plans. Great!

My advice in this situation is to have a specific date in mind. Lead with the activity. Ask in person if possible.

“Would you like to have dinner with me tonight?”

She knows it’s Valentine’s Day–you don’t have to remind her. But maybe your situation is a little more complicated. Maybe you’ve been seeing a lady for a while, but haven’t had the conversation. You know the one–the one where you make it official. Boyfriend Girlfriend. Couple.

That can be a delicate conversation to have at any time, but Valentine’s Day is about expressing how you feel. If you feel that the time is right to take your relationship to the next level, why not use the day to take the next step?

It doesn’t have to be excessive: it just needs to be representative of your relationship. Heartfelt conversation, cringe-worthy (yet adorable) playlist that secretly spells out “be my girlfriend,” surreptitiously changing your address to hers with the SS-5 form (bold! Please let us know how that turns out!), or use the ever classic “brie mine.” Take a chance!

How To Ask a Guy out on Valentine’s Day

 

It’s 2024—ask him out!

Don’t wait for the guy to make the first move if you don’t want to. If there’s a gentleman that you have your eyes on and he’s available, why not ask him on a date?

The further past high school we all get, the more we realize that displaying honest feelings isn’t some game of chicken that leaves us open to mockery. The vast majority of us couple up (it’s how our species survives): it’s a natural part of life. In short: go for it.

The unexpected nature of the gender-norm reversal will be disarming (in a good way!); most men will appreciate it. The rules are the same—it’s the same thing, after all, we’re just making a bigger deal of it for some reason! Again, leading with an activity (dinner, drinks) is always a smart idea; it grounds the offer. Maybe you’ve been seeing a guy for a while but haven’t defined the relationship yet. If you want that- if you feel your relationship deserves to move forward to that next phase—then you owe it to yourself and your significant other to make those feelings known. Valentine’s Day is about expressing your feelings and sharing romance. No one can guarantee how it will play out (he may return that Form 8822 unsigned), but that’s life: nothing is guaranteed.

Taking chances is what it’s all about. Valentine’s Day gives you a great opening and frame for it. It gives us a little romantic push (and a little romantic cover) to be honest with ourselves and those we care about.

Go out there and be honest about how you feel. Respectfully.

Happy St. Valentine’s,

Nathan