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Valentine's Day is nearly half over — and it's not even the 14th yet.
That statement either makes perfect sense or sounds completely absurd. Either way, don't roll your eyes just yet. Valentine's Day has quietly evolved from a single day into an entire week-long affair. It's a popular thing going on and it's actually gaining momentum now. And whether you love the idea or your first instinct is to write the word "gullible" on a notepad, it's worth understanding what's actually happening before you dismiss it.
Valentine's Week: Is It Even Real?
Is the guilt trip extra or do you get that in the base price?
That's the natural reaction when a lot of people hear that Valentine's Day is not just one day — that it is a week-long affair, or can be. It makes a lot of people clenchy. But hold on, don't roll your eyes quite yet, because each day has a very specific focus and it's worth spelling out before passing judgment.
Here's where it gets interesting — and a little suspicious. Try to research when this all started and you'll hit a wall of contradictions. Some people pointed to ancient Rome. Others pointed to India, this far-off land. Still others said no, this is a really modern trend that started with social media. As for who started it? Couldn't get that either, because the origin was so varied. Some even interjected that this was invented by commercial capitalist companies to try to stretch out the week and make more money and make it more profitable.
So you have no idea where this started, when it started — but it's a real thing going on right now.
Why? Same problem. Two completely different answers depending on where you look. Some say it's about expanding sales. Other people said this was an attempt to actually eliminate or reduce or relieve that whole commercial money suck that Valentine's Day has become. It just really depends on where you look for those answers.
But here's what's remarkable. Despite the chaos around origins and motives, there is thankfully one thing they all agreed on: these seven days were an effort to really focus on the different aspects and the different facets of affectionate love. Not the material expressions of it. The relational, the emotional, the things you can't always grasp but you definitely can feel.
And the other thing they did agree on — and this was very impressive — was what the days actually are. When the research started, the expectation was that this would be all over the board with no consensus. But all of a sudden, boom — all the days were named the same and all the days were themed the same. Every source. That kind of agreement, from people who can't agree on anything else about this week, is at least worth exploring.
The history of Valentine's Day itself — the Christian heritage behind the holiday, the people behind it, the events that took place — that's not under dispute at all. That's historical fact. But this week-long lead-up is just one of the ways people have started to celebrate it. It's kind of grown over the years, just like Christmas in July.
Rose Day — February 7th
The week opens with roses, and roses carry a lot more meaning than most people realize.
Flowers mean different things. Giving people specific flowers on specific occasions can have very different meanings behind them. But roses are often associated with a much deeper form of love, a more serious form of love. The red rose being romantic love.
There was a time — not that long ago — when rose colors were taken very seriously. Red roses were reserved specifically for a romantic interest. You would never give a red rose to somebody you were going on a second date with. You'd never give a red rose to a teacher or a grandmother or anybody like that in your life. You'd find a different color rose for them. Red roses were supposed to be specifically for the one and true love. That was the social protocol.
A yellow rose? Friendship. A white rose? Familial love — family, not romantic. Different colors, different hybrids, different meanings. And people took those distinctions dead seriously. If your boss gave you a red rose in the '70s, that would be a problem.
That has faded over the years. But the average person would still look at red roses as a very affectionate, romantic gesture. And that instinct isn't wrong.
Gramster Rant: You're Not the Boss of Me
And that is exactly what our culture has become.
Red roses can mean whatever you want them to mean now. Because you're not the boss of me. That's it — if you wanted a one-sentence theme of our culture, it's "you're not the boss of me." I don't care about your tradition. I don't care about what it used to mean. What does it mean to me? What are my feelings? And you know what? I can give a red rose to my coworker if I want to. It doesn't have to mean anything.
We're deconstructing everything. Every protocol, every tradition, every shared understanding — torn down and rebuilt around individual feeling. That is our culture.
Now, the average person would still look at red roses as a very affectionate, romantic gesture. That instinct hasn't died entirely. Most people would never consider giving an administrative assistant red roses. You wouldn't bring red roses to a lady in the church who's in the hospital. Your skin would crawl — like, what are you doing? Don't you know better than that? At this point, it's probably not even something that happens much in the workplace anymore.
But there are also probably enough people in our culture by now that they just don't know what red roses mean. They have no idea about the protocol. And there's no point in being offended over it when someone genuinely doesn't know. That's where we are — the meaning has eroded to the point where ignorance of it is as common as defiance of it.
And this extends far beyond flower arrangements. It's the same impulse that drives people to deconstruct faith, to deconstruct community norms, to insist that nothing carries inherent meaning unless they personally assign it. The "you're not the boss of me" generation has decided that centuries of shared understanding are optional.
The truth is, some things carry meaning whether we acknowledge it or not. A red rose still says something. And pretending it doesn't just because the culture says meaning is whatever you make it — well, that tells you everything you need to know about where we are.
Now, the beauty of having Rose Day seven days before Valentine's is that it spreads things out. You could kind of have things to look forward to throughout the week. And you could make these days as big and dramatic as you want to or as subtle and simple as you want to.
A single rose. A little bear holding a rose. Or nothing purchased at all — just remind your loved one that they are the sweetest rose of all on Rose Day. It doesn't have to cost you anything. It doesn't have to. That's the point of this week-long thing — to take the pressure off of material things. Have kids draw pictures of roses. Just take one rose and give it to a person.
Propose Day — February 8th
This may not be what you think it is.
Of course you can propose marriage on that day if you want to. But if you're already married, you could just remember the day you got engaged and kind of reminisce about that day.
Some proposals are candlelit evenings on a lake. Others are conversations at 65 miles per hour on the highway. A jarhead soldier driving down the road saying, "Well, should we — should we maybe?" with a ring that had diamond chips in it because that's what the budget allowed. Not exactly a Hallmark moment.
But here's the thing — you can have these laughs and jokes just remembering your very unique story. "Unique" might be putting lipstick on that pig, but couples who lean into the humor of their real story instead of mourning the fairy tale they didn't get are doing it right. That's Propose Day working exactly as intended.
And for those whose proposal wasn't all that romantic, get creative. Re-enact a mock engagement. Go back to the place it happened. Even if it was a courthouse before one of you shipped off to Europe — even if your first child was born in West Germany and your wedding party was a justice of the peace — you've got a story nobody else has. Lean into it.
But here's the broader application: a proposal does not have to be a marriage or romantic proposal. Think of somebody in your life who's very important to you that you love, and call them up and say, "Hey, we haven't seen each other in a while. I propose we get together." Or think of somebody going through a hard time — maybe Valentine's Day is hard for them — and say, "Hey, I propose I take you out for lunch."
Will your friend's reenacted-proposal-on-bended-knee story sound more glamorous than "he proposed we go to Taco Bell"? Absolutely. But it doesn't matter. The reaching out is the point.
Chocolate Day — February 9th
Can't mess this one up, can you? Well, you can. Some chocolate tastes like wax.
To all men listening: don't go cheap on the chocolates for Valentine's Day. Put a little coin in and get better chocolates. If you're stopping by the truck stop and you see something in a heart-shaped box, keep moving. Do something better than that. This is the time to go with the higher end.
Find a nice little imported Belgian chocolate. Even if it's just a little four-pack, go with that. As for brand debates — Godiva has its fans but isn't universally loved. Dove's a little bit better than Hershey's. Russell Stover has loyalists. The point isn't the label, it's the thought. Just think it through. That's all.
But Chocolate Day doesn't require spending at all. For couples who don't often have dessert with dinner, this is the day to break that pattern. A cup of hot chocolate and a movie. A few thin mints. A chocolate kiss with a cup of coffee. Just a tiny little sweet something. What better day on the calendar to get in touch with your inner fat self than Chocolate Day?
The moderation struggle is real — especially moving from your 40s into your 50s and now into your 60s. "We're each going to have just five M&M's" turns into five handfuls, and that barrel from Costco that's supposed to last a month is half gone. The empty cup is jackknifed in the garbage after five days. That's the issue.
But having something planned — knowing that on this day, you're going to splurge a little — actually helps when you're watching what you eat the rest of the time. It's something to look forward to.
For anyone who doesn't like chocolate or is allergic, just fill it in with whatever your favorite thing is.
Teddy Day — February 10th
Let's address the bear in the room. When some people hear "Teddy Day," the mind doesn't immediately go to stuffed animals. There's a whole other connotation from decades past — "I'm going to go put on a teddy" was slang for something considerably less plush. But this is, in fact, about teddy bears.
Do grown women really want teddy bears from their romantic interest? Some do. Enough to make it a day? That's debatable. Some people love the Vermont Teddy Bear thing. Others would look at you and say, "What's this?" Know your audience.
But Teddy Day doesn't require purchasing an actual stuffed bear. Send a meme or a text with a teddy bear and an "I love you." Have kids draw teddy bears — children love them. It's a gesture, not a mandate.
This day also gives a clue about when Valentine's Week may have come into fashion. There was no such thing as a teddy bear before Teddy Roosevelt. They were making stuffed bears before that — the manufacturing started in Germany — but the way the bear became a really popular toy, the actual naming of it as a "teddy bear," would have been at the very beginning of the 1900s during Roosevelt's time as president. So Valentine's Week couldn't have started before the twentieth century. That narrows it down, at least a little.
Like every day on this list, it doesn't have to be a big production. A digital image, a quick text, a drawn picture from the kids. The point is warmth, softness, and acknowledgment.
Promise Day — February 11th
This one comes with a warning: don't let it smack of New Year's resolutions where you're going to promise something really great and then it falls apart and then you're open to disappointment and self-loathing. That's not what it's meant to be.
Promise Day is symbolized by the pinky swear — a throwback to childhood where you'd pinky swear stuff and it was ironclad. The idea is to shift the mindset of Valentine's Day from the material to the relational and the emotional. Look at the relationships you already have and find someone in your circle — seriously, don't mock this — because this could really help someone who struggles around this time of year.
Make a promise. It doesn't have to be grandiose. "I'm going to make sure I don't let a week go by where I don't connect with you." Or: "Let's pinky swear that we're going to take that vacation we always wanted to." Like deciding to walk across Europe for 70 days in your 50s — the kind of thing you were going to do when you were younger but then you had four kids by 27 and life happened.
When you have a united goal with someone, it strengthens that relationship and it deepens that relationship. And that's what it's all about. That's what Valentine's Day is all about.
Now, people should be people of their word regardless. You can make commitments with folks, do a handshake, and do that on a Tuesday in November. It's just as legitimate as Promise Day. But having a designated prompt for those who need the nudge? There's no Promise Day police. It's just a fun idea of a way to strengthen the relationships you have with your loved ones because that's what love's all about.
Hug Day — February 12th
This is a day where we kind of remind ourselves that we need that human touch and interaction in our lives. Maybe there's somebody who needs a hug. Find that person today. Maybe it's you.
We're becoming a culture where we're going to be sterile. We're going to have our phone. We're going to be inside. We're not face to face very often. COVID really sparked that fear in people to connect. And yet, human touch is very therapeutic. It's a need. Psychologists have proved it. There's been research. There's been testing. Hugs are a good thing.
But — and this needs to be said directly — there is a percentage of the population that doesn't want to be hugged. When you hug them, you get the exact opposite reaction. People who are always standing at the door trying to hug everyone will hug ten people and five or six or seven of them will be a positive experience and three will be horrific. To the point where they'll complain about it.
You can't go around hugging people at work anymore. Why? Because people get uncomfortable. For every one that wants a hug, there might be five that don't. The person who announces "I'm a hugger!" and moves in without asking isn't spreading warmth. Just because you are a hugging, touchy-feely person doesn't mean you get to impose that. You didn't ask. Nobody runs around preemptively saying "I'm not a hugger" — that's not how it works.
Everything can be taken to an extreme where it's like, don't do that. On Hug Day, we're not talking about strangers. We're not talking about people you don't know. We're talking about people you do know and people you love and care about.
For those who aren't huggers, there are other ways. One couple bought matching Hug Day hoodies, and every year on February 12th they'd wear them — because one of them was not a huggy person, but they'd put that on and it was still a sense of love. It was warm. It was soft. And that's what they're talking about. It's about making the human connection. It's not about invading people's personal space.
A cup of cocoa with a movie checks off a lot of the boxes on this list. Send a little emoji hug. Even if it's your normal goodbye-to-work hug with your spouse — hey, check it off your box. You had Hug Day today.
Kiss Day — February 13th
The last day before Valentine's is Kiss Day. And of course, not everybody does this the same way.
This can be a romantic thing, but it does not necessarily have to be. You can find a lot of different ways to send a kiss to somebody without actually planting your lips on them. If you've got grandkids that are far away, send them a little text with a kiss and a hug. A mother always enjoys a kiss on the forehead from one of her children. That's always a very, very loving thing.
That's what these days are all about — just remembering to connect and keep forging those relationships because if you don't, they grow cold.
Common sense applies. It's not a day to go around blowing kisses to everyone. There needs to be limits. There needs to be common sense.
The Pressure Guys Carry
Here's what Valentine's Week is actually wrestling with underneath all the themed days.
If you took this week-long concept and told most guys, "Hey sweetie, let's celebrate Valentine's Week — it starts on the 7th and goes through the 13th and culminates with the 14th," every guy is thinking the same thing: This sucks. This is going to be awful because I'm going to fail. I'm not going to do it right. Something's going to be wrong. It's just more pressure.
February 14th already brings a lot of pressure.
Almost all salt-of-the-earth men — this romance stuff does not come naturally. And when you rip off the veneer, they want to be good at this. They just really feel they're not. And that no matter what they do, they're not going to get it right.
What 60 to 70 percent of guys want out of Valentine's Day is simply for her to be pleased with his efforts. That's it. No matter what he does, in the back of his mind — just a little bit — he's second-guessing. Is this enough? Does she really understand that this is what I think this day is worth?
Giving her one single rose because she's the only one — cheap, she might think. Or she might think, That's so romantic. I didn't want the other eleven. I just wanted this one rose. It depends on who you married.
And here's the kicker: she was this way last year. Last year, he gave her one rose and it was so special. So he tries it again this year to find out that only worked last year. This year, she's expecting the other eleven. A guy never has confidence that what he's doing is enough. Even if she shows great appreciation, there's a little doubt in the back of the mind. Why? Because of the comparison trap that human beings put themselves through — comparing each other to what Sally down the road got, or what Ginger at the office got, or what her sister's husband did.
That is the challenge with Valentine's Day.
True story: There's a guy — one of the most wonderful dudes in the world, not someone you'd peg as a romantic — who went out and got his wife this big vase full of huge flowers. He wanted to put it in the church for Wednesday night so she could discover it when they came for Bible study. He met up at 2:30 in the afternoon to set this arrangement on the table. She comes in, he's walking with her, waiting for her to notice. She notices. And the first thing she does is turn to him, tap him on the shoulder, and say, "This is a lucky lady. How come you never do anything like that for me?"
She was wearing a Disney shirt that said "Grumpy."
You can't make this up. And this is one of the greatest couples you'd ever meet — a fond, warm memory for everyone who witnessed it. But it perfectly captures the dynamic. A guy never knows if what he does is going to land the way he hopes.
And then there's the other side of the story — the gentleman who bought a single-stem rose for his wife every year for Valentine's and brought it home after work. Then she passed away. He was elderly, by himself. And he kept — for the rest of his years — buying a single rose. He'd put it in his lapel or wherever. Just because his wife was gone, he didn't stop doing that. Those little things can mean so much, and the big things can mean so much, especially when they're unexpected.
The Pros and Cons
The Cons
When people hear about Valentine's Week, right away the mind goes to: I've got more stuff I got to do. This type of thing can very quickly and very easily become overwhelming for people who have very hectic lifestyles or people for whom this type of stuff just doesn't come naturally.
There's also the risk that you're too busy, so you just fall into buying your way through it, and then you end up spending more money than you would have — and that's not the point.
And there's a legitimate concern that all this lead-up turns the 14th into a deflated big nothing burger. If you've been doing roses, proposals, chocolate, teddy bears, promises, hugs, and kisses all week, does the actual day still feel special?
The Pros
There's no police saying you have to do this. It's not so popular that everybody expects it. And it's perfect for people who show love this way naturally.
But the strongest pro is rooted in something that's been proven over and over in marriages: anticipation beats surprise.
The conventional wisdom says the ultimate romantic gesture is the surprise getaway — pack her bag, convince her boss to give her the half day off on Friday, come get her at lunch, and whisk her away to that bed and breakfast you've been talking about. And that can be wonderful. But what's been proven over and over to be better for marriages is telling her two weeks out. "Hey, two weeks from Friday — this is what we're doing."
Why? Because then for two weeks she tells her coworkers. She tells her girlfriends. She tells her sisters. For two weeks, she's thinking about what he did for her. You get the big crescendo with the surprise, but you get this buildup that is much bigger and better at the end of the day. One just is a better way to do it if you're looking to build a long experience versus just the one bada bing bada boom.
Valentine's Week can be that. Things that take place during the week that your loved one will think about and remember. Your spouse feels loved for eight days rather than just one. And it doesn't matter if it's the wife doing it for the husband or the husband doing it for the wife or both doing it together. It makes the other person feel loved and appreciated. It really, really does.
It can actually end up having the reverse effect — instead of adding pressure, it takes the pressure off the actual Valentine's Day. You don't have to book the table at your fourth-favorite restaurant because all the other ones are full. You don't have to spend the extra money to sit two feet away from the next couple as they cram the tables in.
Breaking the Rut
It's so easy for people to get into a rut. "What do you want to do? Go out to eat? Go to a movie? What movie? What restaurant?" It gets old to where you don't even want to do it anymore. The same old, same old of long-term marriage — it's real. And you've got to try to find some variety to do different things.
Some couples fight the rut with ongoing little traditions that have nothing to do with any holiday. A clown nose from a Walgreens charity drive, hidden back and forth in increasingly creative locations for over a decade, never once spoken about. You hide it on the other person, they find it, they hide it back. The key? Until the moment it comes up, you've never spoken of it. That's the magic.
Put it in the Excedrin bottle — he's not going to have a headache for three or four weeks, but he'll open it and there it is. Put it somewhere right out in the open on something that belongs to them, and see how long it takes. The minute it's gone, you know they did something with it, and then you're on the lookout.
A miniature little toy Jesus, tucked into a makeup box or hidden in a coffee mug, waiting to be discovered. "I found Jesus" takes on a whole new meaning when you open your stuff and he's staring back at you.
These tiny, recurring, secret gestures keep a spark of playfulness alive in ways no single expensive dinner can replicate. And that's exactly what Valentine's Week offers at its best — a popup to get out of the rut. Seven days of small, attainable, intentional gestures that remind someone they're thought of. They don't have to be extravagant. They don't have to cost anything. They just have to be genuine.
Because when something is contrived, you spot it immediately. Just like in our walk with Christ — when we see false teachers and people walking a contrived Christian life, it pops off the paper. When you're walking that narrow path with Jesus, sold out, content in your circumstances because of his great gain in your life — boom. You spot the fake. The same is true in love. Genuine care stands apart from performance, and the people closest to you can always tell the difference.
The Contentment Principle
This goes back to a spiritual principle that matters deeply and that also goes back to what Valentine's Day is really about: being content.
Men out there — whatever effort you put forward, if you do it with genuine love for your spouse, feel confident that it is enough. And for all the women out there — whenever you get anything, feel like it is enough. Contentment with godliness is great gain. That applies to February 14th as much as any other day of the year.
That's what this is about. Tuning into the lives of the people that you love. Knowing what they would appreciate. Knowing what they really, really care about. And acting on it — not because a calendar told you to, but because the calendar reminded you to.
Final Thoughts
Valentine's Week is a real week. Nobody knows exactly where it started. Not everybody believes in it. And the running objections — gullible, deception, possible malarkey, buzzkill, contrived, and fear — are not entirely without merit.
But strip away the skepticism and what remains is simple: it's about remembering to connect, keeping those relationships alive, and being intentional about the people who matter most. Not just romantic love, but friendship, family, community — the full spectrum of human connection.
Nobody's policing it. It's not expected. There's no obligation. It's just an option for the people who want to make love a little less about one high-pressure dinner and a little more about showing up, day after day, in ways that are completely attainable and don't have to cost a thing.
And if the whole concept still sounds like seven extra days of trying not to be a failure? Fair enough. Just don't forget the 14th.