Cupid Misses His Mark: 45 Times Valentines Became the Saddest Day of the Year

By Jhoana C

The first person to record St. Valentine’s Day as a romantic occasion was the poet Sir Geoffrey Chaucer who mentioned it in 1375 in his famous poem ‘Parliament of Foules.’ Also, although there are countless martyrs with the name Valentine, there’s a big chance that the day got its name from a priest who was executed by the emperor Claudius II Gothicus for performing secret marriages in Rome.

Valentine’s Day became truly commercialized early in the 20th century when Hallmark mass-produced cards. Nowadays, it’s hard to miss this important day. Aside from the constant barrage of advertisements, you’ll also see plenty of paper hearts hanging in stores everywhere. However, Valentine’s Day is not a happy day for everyone, as you will see in this listicle. You can count yourself lucky if none of the things below has ever happened to you on VDay.

#1 Too cheap to buy flowers

Flowers and chocolate are classic Valentine’s Day gifts. Aside from the day of hearts, men buy flowers and chocolate for the women they love during special occasions such as birthdays and anniversaries. Or occasionally, when they know they messed up somewhere and are looking to appease them.

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Women generally love receiving flowers and chocolates. Well, except on the occasions when they’re not made aware that the gifts were actually bought with their own money! How would you feel if you found out that your significant other bought you expensive flowers using your credit card?

#2 Mistaken as a couple

Valentine’s isn’t so bad, even if you’re single. Nowadays, you can do a lot of things to make Valentine’s just as enjoyable when you’re not in a relationship. But what’s the one thing you don’t expect to happen to you during the day of hearts?

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For this guy, it was being mistaken for a gay couple. He had a flat tire, and his friend was kind enough to bail him out, so he thought, what better way to say thanks than treat his buddy to dinner? Well, at least people thought they were cute!

#3 It’s not like it’s a fart

It’s quite alarming to realize that many men are ignorant about what goes on in women’s bodies. It’s no longer the medieval ages, folks! Science and technology are way more advanced, and information is everywhere. All you need to do is read or watch a video.

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Don’t be a douche like this guy who lost it when his girlfriend got her period during Valentine’s. It’s not like it’s a fart that you can hold in. Aunt Flo comes whenever she wants, and there’s nothing you can do about it but ensure you have enough tampons!

#4 Good riddance

Sometimes being in a relationship with someone who doesn’t value your presence in their life is just too draining, so you break up with them. No point in making all the effort for them when they won’t do the bare minimum for you.

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This breakup may have happened on the worst day to get out of a relationship, but we say it’s better to nip things in the bud. Guys like this aren’t going to change. This guy and the “you couldn’t have held it in” genius both didn’t deserve these women.

#5 Another guy to be rid of

Girls and boys everywhere, listen to us; never lower your standards. Granted, your prince might take some time to come, but it’s better to be alone than to be in a relationship with someone who doesn’t respect, value, and love you, even if it’s only for a short time.

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This is a lesson on who not to give a chance, even if they are the most persistent person on earth. We can’t wrap our heads around what this guy’s idea of a date is. 15 minutes for the whole thing and only paid for his food? What was he thinking?

#6 What a sweet gesture

Valentine’s Day is not just for lovers; it can be about celebrating the love of our parents too. When you become a parent, it is easy to forget that you also have a spouse that needs your love and attention.

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This sweet gesture is something every parent secretly wishes for. But without the potential fire, though! Valentine’s doesn’t have to be loud, dramatic, and over-the-top. Even the little things can make people happy, like breakfast in bed. So, if you’re out of ideas on what to do, think simple and thoughtful.

#7 This guy deserves to be dumped

When you get into a relationship, there is an assumed understanding that you are exclusive unless otherwise agreed upon. Even if you are not the one initiating conversations, it’s still not proper to flirt with other people. However, not everyone thinks like that.

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Aside from the cheating, this guy didn’t even want to acknowledge what he did, which was a bigger slap on the face. The lady dodged a bullet with this one. He deserved to get dumped. Also, who buys pre-Valentine gifts after being accused of cheating? It only makes you look more guilty, right?

#8 You got burned

A little research on the net would tell you that candles became popular again during the ’80s and ’90s after being out of style for a while. Aside from being common gifts and decorative pieces, candles today are also tied to romance, hence the popularity of candlelit dinners.

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Yes, it’s cozy and romantic to have such a dinner, but you have to be careful, or you could end up with singed clothes or worse, be blamed for a fire you didn’t cause! Candles are fire hazards, and aside from losing your hair, you could end up losing a potential partner too.

#9 Girls from hell

If you think Mean Girls are only onscreen, then you haven’t been near a high school. Some girls are not only catty; they can get really nasty sometimes. Although a few laughs are alright, it is never okay when it is at the expense of others.  

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Being invisible and unpopular in school is already hard enough. You don’t need a group of beautiful, popular girls making you the butt of a mean joke on Valentine’s Day. We can only wish that those girls got what was coming to them.

#10 The pain of unrequited love

We’ve all been here, professing our love for someone who doesn’t love us back the way we want them to. Well, perhaps not all of us were courageous enough to do it, but if the other person does not feel what we feel, it’s gotta hurt just the same.

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We can only imagine the heartbreak this person got after confessing her feelings to her best friend, only for him to reject her. What’s worse, he kept going on and on about how he liked this other girl, which crushed our girl here. We hope she had a better Valentine’s the following year.

#11 No money for Valentines

While some men are generally bad at remembering significant dates, that’s no excuse to forget special occasions and certainly not a reason to be cheap during important events. We understand that money is tight at times, but that’s different from being totally stingy.

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How would you feel if you went all out on Valentine’s Day only for your partner to give you a t-shirt you already owned as a ‘gift’? We can only hope that this lady said ta-ta to her cheapskate of a boyfriend.

#12 The stuff of nightmares

Family reunions are, more often than not, the stuff of nightmares, especially when current and ex-family members decide to show up. Yup, we mean former wives and husbands. It’s uncomfortable and something you want to get out of as fast as possible.

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Wonder what could make the awkward situation even worse? A clogged toilet. Especially one that’s only a few feet away from where everyone is having dinner. We can only imagine the embarrassment on this person’s face when everyone realized what they had done.

#13 That was awkward

These days, people are opting to settle down later in life after they have gotten their careers and finances sorted out. Gone are the days when women and even men felt pressured to get married before they reached the age of 25.

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You have to make sure you’re financially ready before you take the plunge. After all, marriage entails a lot of responsibilities; it’s not all romance and good times. This woman wasn’t ready to get married yet, but do you agree with how she handled her now ex’s almost proposal? Sure ruined Valentine’s for him.

#14 What a mean old step-grandmother

If there was ever a contest for the meanest step-grandmother, this lady would get the grand prize. Kids are innocent, and regardless of whether they’re related to you or not, they should be treated right. If you’re going to give a gift to one grandchild, you need to gift the rest, too, step or otherwise.

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Luckily for this person, her stepmother seemed like a decent person and understood how she felt after seeing her stepsisters get enormous gifts. So, she made the day about her, which, frankly, was an amazing thing for her to do.

#15 Valentine’s Day is for all genders

Contrary to what most people believe, Valentine’s Day is not just for women. While it’s true that men woo them with chocolates and flowers, men need some affection and wooing too. Romantic gestures are not only reserved for the ladies.

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If you’re going to say or at least hint that you are going to get someone a gift for Valentine’s, make sure you follow through because if you don’t, they will only feel bad and resent you for it. Ladies, don’t be like this woman.

#16 The Valentine’s breakup

Breaking up with someone is never easy, especially if it has to be done during the day of hearts. Nobody wants to be left alone during the most romantic day of the year, but if you really had to do it, would you choose to delay it or just get it over with it?

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Aside from having to deliver the bad news during Valentine’s, this girl also had no choice but to sleep over at her ex’s home because their train ride home wasn’t until the following day. We can’t imagine a longer night than the one these two had that fateful Valentine’s. Total disaster.

#17 Creepy guy and creepy date

There’s a difference between being cheap, being broke, and being creepy, but this guy seems to have combined it all. You don’t have to be the richest guy to afford at least a decent Valentine’s dinner. But since he just wanted to get some action, he didn’t even care to find a suitable venue.

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Aside from bringing his date to a creepy, dirty beach frequented by homeless people, he also just bought a small box of pizza, which he clearly didn’t want to share! This definitely fits on a list of the worst Valentine’s dates ever. Poor girl.

#18 From romantic to creepy really fast

Would you be happy to receive a surprise bouquet of your favorite flowers from your boyfriend? We bet you answered in the affirmative (if he exists at all!) But what if the bouquet came from someone you don’t know and didn’t have any card? Would you still be overjoyed with the surprise?

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What if the same person who sent you the roses happened to drop by your home unannounced and left you a message on the snow? Romantic can become creepy really fast, especially when you’re being stalked by someone you don’t know. Be safe out there!

#19 Better off as an ex

If you want to break things off with someone, you better do it as soon as possible, and you better be honest about the reason. There’s no need to hold back information. You owe it to the other party to let them know why you think it’s not a good idea to continue with the relationship.

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Nobody wants to be in this guy’s shoes. His girlfriend told him that they should go on a break shortly before VDay, but then he found out that she had gone back to her ex. Well, he’s better off without her, if you ask us.

#20 Not cool at all

If you’re bored, there are plenty of things you can do with your free time, such as volunteer or help neighborhood kids by tutoring them. You can also watch a movie or series on Netflix or read a book, but here’s an obvious example of what you must never do.

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Now, this was just mean and completely unnecessary. Making fun of other people, especially on Valentine’s Day, is a big no-no. You could end up hurting someone’s delicate feelings or making them look like a fool. Was it really worth it?

#21 He took all the trouble to break up

Are you a quiet type of person, or are you someone who likes attention? If you were going to break up with someone, how would you do it? Would you want it to be a private, civil conversation, or do you have a flair for the dramatics?

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Well, we all know what category this guy belongs to. Why would you spend money on black and dead roses just to break up with someone? We wonder if the girl saw it coming, but then again, how can anyone predict something like this?

#22 Grandma’s gain

Here we go again with young love. It’s one of the most beautiful experiences you can ever have, but it can also be the worst, depending on who you fall for. Either way, one thing’s for sure; these romances will teach you a lesson.

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This guy’s ex’s loss became his grandma’s gain. We bet grandma was over the moon when she received this wonderful surprise! We also can’t help but sympathize with this very short-lived romance. Does she qualify to be referred to as an ex after a week?

#23 Waiting for marriage

We can think of many reasons why some people choose to wait until marriage to do it. We respect them and also accept the rest who choose to do it before marriage because we all have our beliefs. To each his own.

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What we’re not cool about is people forcing others to do things they don’t want to just because they spent money on presents. Dude, you were not owed anything, especially since the girl had been so clear about where she stood on sex before marriage.

#24 VDay at the ER

Some of the most common food allergens are peanuts, eggs, wheat, soy, shellfish, and fish. We can’t imagine a life where you’re not able to eat certain food for fear that you will break out in rashes or, worse, have difficulty breathing.

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However, that’s a reality other people have to live with daily. This girl is no exception. The only problem was her boyfriend didn’t realize one of the chocolates he got her had nuts in it. Fortunately, nothing severe happened, and they ended up having a memorable Valentine’s Day, albeit for the wrong reasons.

#25 What an a#%hole!

If you’re not sure about someone, at least tell them so that they know if you’re seeing someone else or if you’re just not ready to be a couple. Sometimes people are just not 100% sure yet, and there’s no problem with that as long as they are open.

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You certainly don’t want to be in this woman’s shoes who thought she was special only to find out that the man she was dating split her bouquet of roses and gave them to her and six other girls! If this was you, would you continue seeing them?

#26 A serious case of ghosting

Ghosting is a new phenomenon that doesn’t involve spirits. It is the term used to describe the act of ending a relationship by stopping all forms of communication without any explanation. Thanks to this inconsiderate practice, this girl’s Valentines essentially became Halloween.

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If you have respect for the other person in the relationship, you should at least have the guts to break up with them personally. We understand people fall out of love all the time but at least have some decency.

#27 How can you forget Valentine’s?

As forgetful as some people might be, Valentine’s is hard to miss. Why? Because you see stores adorned with red hearts and other things associated with love and romance, such as chocolates, flowers, and all sorts of Valentine’s-themed gifts. Suffice it to say it’s an in-your-face occasion.

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However, some people still forget it, conveniently too, if we might add. This lady can still consider herself lucky because, at the very least, her boyfriend still got her something, even if it was from CVS. Some people are not as “lucky.”

#28 A happy ending, for a change

Valentine’s Day horror stories are a dime a dozen these days, and in a world where there’s so much negativity, we all need a happy ending every now and then. It’s the reason why Hallmark movies and romantic comedies exist!

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This is the kind of Valentine’s Day story people yearn to have. Stories like this make us believe that there’s someone out there for everyone. All you need to do is be open to the possibility (and ask these guys for the secret code!)

#29 Making hearts flutter

The early stages of a relationship are the most exciting; that’s why it’s called the honeymoon stage. You constantly want to be around each other and just hang out. It’s also normal for couples to want to show off their significant other, even if it’s only on their phone screens.

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This guy wasn’t even in a relationship with the girl of his dreams yet. They had only just met, but he already had her face on this phone’s screen. Do you think that’s sweet or a bit creepy? We wonder how that date went.

#30 Too needy or not?

What are the signs of being needy? Constantly wanting all the attention and feeling that your life would be boring, empty, and lonely without a particular person are just some of the examples given by many. Would you categorize yourself as needy?

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If your girlfriend acted like this, would you be upset? To be fair, if our significant other called expressing our feelings a game, we wouldn’t be pleased. But perhaps she was really saying “I miss you” too many times. That can be annoying.

#31 The same song for every girl

When someone writes you a beautiful love song, you’ll surely be flattered, and you just might say yes to the guy and become his girlfriend. However, if he writes you a crappy song and says bad things about you after you turn him down, it’s a different story.

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Not only did this guy recycle the same love song he had supposedly written for every girl he had been with, but he also had a bad attitude and couldn’t take no for an answer. If you ever come across a guy like this, run for the hills.

#32 Makeup disaster

Being made up makes women everywhere feel beautiful. That’s why they bring out all their expensive products and go all out, especially during special occasions like Valentine’s. Nobody wants to look like they just got out of bed when going on a date during the most romantic time of the year.

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This is a warning to only get your makeup done by professionals during special occasions. You don’t want to end up like you’re going trick or treating instead of having a romantic dinner with your significant other. What a disaster!

#33 Double date with parents

Going on a double date can be fun and exciting if you know the other couple and get along well with them. Double dating with your boyfriend’s parents can be equally enjoyable, too, provided that your boyfriend’s parents like you.

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However, it’s a different story if your boyfriend’s mother does not like you. We can only imagine how awkward this Valentine’s date must have been. We bet the OP couldn’t wait to get out of there and just go home and curse at the gods of Valentine’s day!

#34 A reason to stay away from dating apps

Dating apps are a dime a dozen nowadays, and most people we know have profiles on several of them. It can be fun to meet random people. Who knows, one of them might turn out to be your prince. But we’re here to warn you that there are plenty of frogs out there too.

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Another horrible date. This is the kind of guy you want to get away from as fast as you can. He’s not even looking for a real relationship; he just wants a quick rebound. Make sure you get to know people before you go on dates with them.

#35 This one is hilarious

Just to put it out there, there is no evidence suggesting dogs understand what is happening between two people when they’re doing it. They might recognize the smell of pheromones, but that’s about it, so don’t worry if you have dogs.

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It’s another story, though, when your dog feels the need to constantly be in the thick of the action, even when that action has nothing to do with them. We can’t even imagine how the OP and their boyfriend felt when their dog decided to throw up right after they did the deed.

#36 Good gift gone bad

Teachers are thought to be a child’s second parents. After all, next to parents, they spend the most time with the child. They are there not only to teach kids their ABCs and 123s but also to guide them. Bless their hearts.

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However, there are instances when a teacher’s good intentions end up not having the desired effect. This teacher spent her money, time, and effort to get her students a gift she thought they would be able to use, but things didn’t turn out how she anticipated.

#37 Totally blindsided

In some relationships, you can see the ending from a mile away, but there are times when you think everything is fine and dandy, only to be hit in the face with the cruel reality. We’d rather be told straight to our faces that something’s wrong rather than get an unpleasant surprise down the road.

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This girl got the double whammy. She was dumped on Valentine’s Day, which also happened to be quite close to her birthday. To make matters worse, even her birthday present had something to do with seeing her ex at a concert! Sending love and light.

#38 Not a funny prank

Ah, middle school and all its drama; mean girls, peer pressure, teenage angst, and young love. At that time, you think you know it all, and no one can convince you otherwise. It’s also in middle school when most teens believe they have found the love of their life.

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This is also the time when all the guys are into pranks, not knowing that they can have a lasting effect on people. It must have been a long couple of weeks because being made fun of by a crush and having it broadcasted to the world is not something we’d wish on anyone.

#39 Why wait until dinner?

We really don’t know what’s going on with some men who think it’s totally okay to break up with someone during a romantic dinner. Why wait until dinner? Just cancel it, sit down with your girl and spill the beans.

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For heaven’s sake, don’t do it in a public place because, most likely, the girl is just going to embarrass herself. Who wouldn’t sob uncontrollably after the love of your life tells you that he doesn’t want to be with you anymore?

#40 Mama’s boy

A mama’s boy is defined as a man who has an unhealthy dependence on his mother. All decisions, especially major ones, must have his mother’s stamp of approval, even if he is already an adult. We have one piece of advice for all women out there, stay away from mama’s boys.

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Respecting your mother is a must, and we understand that. However, mothers must also understand when their sons get married and give them space. Most importantly, the guy must find a way to communicate that otherwise, he’ll be spending Valentine’s at home for the rest of his life, like this guy.

#41 Allergies are a bummer

According to estimates, as much as 10% of the world population has food allergies, and that number does not show signs of slowing down anytime soon. When severe, allergies can cause anaphylaxis, which can lead to death if it goes untreated.

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Thankfully for this couple, the guy’s allergic reaction wasn’t very severe. However, you could say that it ruined their day of hearts and the week after that. Guys, before you buy anything to be used in the bedroom, make sure that no one has allergies to it.

#42 What a loser!

Giving someone a gift is very thoughtful, and being given a gift makes you feel valued and appreciated. However, this doesn’t mean that you should put too much value on them. People who can’t buy gifts can still give their time and attention to you, two priceless things.

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This guy, however, wanted nothing else but to get a gift on Valentine’s Day. After getting what he wanted, he had the audacity to break up with the girl who had made all that effort to make the day special for him. We hope she left with that notebook!

#43 Immature teenage love

Teenage love is a part of growing up. It’s something you can’t skip. Even if you didn’t have a boyfriend or girlfriend at that age, you certainly liked someone so much that you thought the world of them. Although most teenage relationships don’t last, there are some that make it to marriage.

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Before this, we didn’t know just how many couples break up on Valentine’s. Really, it’s like an epidemic! From the way this guy treated the girl, it’s easy to see that they weren’t going to go the distance. We’re sure it hurt a lot, but girl, there’s a whole big world out there.

#44 Model husband…not

The ideal husband is someone who supports his wife 100%. He should be just as active and present in the home as he is in the workplace. Gone are the days when men only went to work and expected to be treated like kings when they got home.

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However, this person must not have gotten the memo. While his wife was busy cleaning their daughter’s puke in the bathroom during Valentine’s Day, all he did was sit in front of the TV. He didn’t even get his wife something special for the day. That really sucks.

#45 Break up via chocolate

You’ve heard this many times. When someone wants to keep your relationship a secret, there’s a big chance that they’re not being 100% honest. They could already be committed to someone, and you’re just a side chick or side guy. Or, they could also be a criminal!

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Seriously though, secret dating is fun and exhilarating, but you have to prepare yourself for the consequences because the truth is nothing good comes of secret dating more than 90% of the time. This lady’s guy broke up with her with chocolates on Valentine’s. But at least the chocolates were good.