In comes the flirting experts! If you’re having a dull day, not to worry! We are here to save you and bring a smile, if not laughter, to brighten up your day. Flirting can be very tricky, but sometimes when it goes wrong, it leaves you with the most hilarious conversations. Here’s a list of unfortunate flirting fails that scream pure comedy.
Yes, You’re Cute
This is just another light-hearted way to steer the conversation, showing that the person has an interest in you. Even though there’s some conventional wisdom, in terms of striking up similar statements, a reactive approach is always the better option to pick.
Even though most of the time, they are just genuine humor and light-hearted jokes, they tend to create a residual impact that keeps hitting at the back of the mind of the person.
Showing Off
This can be interpreted in different ways depending on the cultural context of people. Inviting your partner over to meet the folks is a sign of commitment and seriousness in building a stronger relationship.
On the flip side, though, merely showing off your partner to your friends also implies that you’re taking him as a trophy partner – not quite seriously. It’s either one of the two. Try to decipher that. If it’s the former, you’re in luck.
The Guilt Trip Is Real
Yes, we agree! Nothing can be more agonizing than stepping on your most beloved tiny friend’s little tail. What’s worse is that you can’t even explain it. The poor animal just whimpers in pain and runs away to some corner of the house away from you.
We would definitely prefer a broken heart over that any day. We wish there was a common language with the animals so we could explain our innocence to them and tell them it was an accident!
Don’t Forget Your Inhaler
The tendency of human beings to crave attention can be magnified by pulling off an act of letting your partner down. That would either make the person react in a very passive way or just reply normally, but deep down inside, you just set the perfect timing to bring up the wild card – the same thing you meant, but now it has a bigger impact.
That is why “playing hard to get” can lead to immense success in dating.
Elaborate Name
The energy being reciprocated here is a sign of mutual interest. On the other hand, the excessive detail laid out by the person in saving the contact information also implies a healthy obsession.
This pair might have a potential journey up ahead even though this does not guarantee stability or compatibility. Since the obsession is viewed positively by the other person, though, there is little chance that anything might go wrong.
No Sea Seeing
We have to say, this went from cute to ugly pretty fast. That poor girl probably thought that she was going on a trip or something with her lover. However, like a poor child with broken expectations, she learned that all she’d be getting is blue toilet freshener.
We don’t get the point of raising her expectations like this just to make them fall. Oh well! At least she’s getting an air freshener out of this.
Heart Burglar Alert
Come on, man – this is just too old now. People have got to start being a little bit more creative and come up with new pickup lines. Not only was this old, but also cringe-y. We don’t know about you, but this sure is making us wonder if the girl ever replied to this.
Judging by the fact that it shows Rachel online, but she’s still not replying, we guess not. Oh well! Better luck next time.
A Walk to Remember
Statements like these open paths to important human psychological phenomena that are taken advantage of in dating or flirting- the craving for attention. There are multiple ways to do it. The technique followed here is letting your partner guess the obvious and then putting her down.
This makes your partner crave attention at this point. This would be the perfect time to say it. What you are actually doing is creating the perfect ambiance to say something that is impactful.
Don’t Be Late Now
This is a nuisance anyone who ever dated a girl would understand. No matter how early you tell them to get ready, they almost never get done in time. So, this was quite a wise decision on his part to let her know a day before.
Hopefully, if she starts getting ready now, she’ll be done by the time they have to go tomorrow. Good thinking, pal! Maybe we should try this out sometime too.
Officially Flirting
We all love to make our relationship official. It’s the step towards the bond of a lifetime. While we love to make every stage official, one of those stages often gets ignored. If we can make our relationship official, why can’t we make the flirting official too?
After all, it’s the very beginning. This couple started to make their flirting official, and we are all for it. We definitely agree that flirtation is in the eye of the beholder.
The Test of Realism
This is the true test of genuineness, it seems. All you have to do to check if a girl is being real with you or not is to look and see if she’s sucking in his stomach or not when she’s meeting you. At least that’s what the guy thinks anyway.
So, if your girlfriend is comfortable with showing off her pooch, then rest assured that you’ve landed a gem in your hands. Keep her and never let go.
This Was Funny
This puts every ‘we need to talk’ conversation to shame. We love how the girl just passively elongates and refuses to have this conversation. He seems like a fun guy – keep him, Mary! It does make us curious about what the guy wanted to discuss, though; judging by the girl’s reaction, it doesn’t seem like it was anything important.
On the other hand, we wonder if the girl even understood the seriousness behind the guy’s text.
Weird Energy
We think this couple’s weird energy is the cutest thing ever. The starting of a relationship is always filled with excitement, fear, and definitely some love. It is a whole rollercoaster of emotions.
People always look back at their beginning with all those emotions and feelings. This couple is no different. Their weird energy blended with the cutest emoji is the reason why this earns a place on our list.
It’s U
We don’t know if this is more cute or funny. We think it falls in both of the parts. We guess the person who gave a picture is a bit of “Chandler” from Friends. We all want a little sarcasm in the relationship.
It just makes it more fun and strong. This picture will work in the sarcasm list too. We think it would be at the top of the Chandler Bing Flirting techniques!
Who Are You, Again?
This was just plain stupid and hurtful. No wonder women have so many trust issues when dealing with guys. People like these ruin the reputations of the good old guys too. Stop lying! If you can’t even remember her name, we are pretty sure she didn’t mean anything to you at all.
If you’re reading this, Glenda, please block this guy and never see him again. You have our support, sister!
Weirdo
The acts of “Flirting” and “Being weird” have a very thin line. This particular picture is an example of that. We don’t know what makes it more fun; the straightforward way of asking out or the sarcastic reply.
We think the person asking the girl out only decided to talk about the full plan so that there is no confusion. We guess the girl did not like the plan. Poor weirdo!
Getting What?
Well, this is embarrassing. Some words can be misleading and cause the embarrassment of a lifetime. This can go on the “flirting gone wrong” list or anything related because, well, look at the text.
This person revealed his true feelings about something that he was probably not expecting. The response was supposed to lead to a different conversation than this one, but what can we do against the will of destiny?
Hurt Stranger
It’s always a little creepy receiving such messages from an anonymous number. Assuming it isn’t a random person, we sure hope this guy doesn’t actually end up hurting his sweetheart by his annoying typos or spelling mistake.
An advice to all the guys out there: if you really want to impress a girl, double-check what you’re sending her. There’s nothing more unattractive than dumb typos. Refrain from trying to flirt with strangers too!
Ross – Is That You?
This definitely reminds us of the relationship between Rachel and Ross in the show Friends – if Ross was as funny as Chandler, that is. This actually reminds us of the painful breakup after that, though.
We are all hoping this one doesn’t end like that. However, at the same time, we also have to laugh at the response. Look at it based on facts – he did give her what she needed from him.
Bragging a Little Too Much?
We all brag to our partner about things. It is much more in the beginning years when you are trying to win the extra brownie points to be on the favorite side. Sometimes, we go too far. This one is an example of this.
The reply to the question was just perfect. The picture in the message said everything. Everything is fair in love and war, after all. There is nothing like too much.
It Was Really Dark
We all want to see our loved ones at all times. It makes us happy. This guy was no different. He wanted to see his beloved one no matter what. He asked for a picture. He didn’t care that it was dark or that it was really, really dark.
So, he got the picture, and guess what? It definitely was dark. Love makes us blind too. We don’t see anything except the person – sometimes not even the person.
No Meetups
Was this a joke? Was this really an unknown number? If so, it sure is funny, and if it was not supposed to be a joke, then that’s actually pretty sad. We love how eagerly the guy texted to meet the girl, but as soon as she declined, the tone of the message changed right away.
It went from eagerness to anger really fast. Now, he doesn’t want to meet her either. We hope the couple makes up, though.
Maria and Her Dirty Sink
Well, Maria got in the mood pretty quick. If we look at the facts, she did what he asked for. In her defense, he never specified what kind of a dirty picture he wanted.
She sent the picture of her dirty sink when he asked for a dirty picture, and we all love her for it. Sometimes, you have to be creative and sarcastic enough to make these lists and make people laugh.
First One
Okay, this is adorable. We all want to be in someone’s thoughts all day. The whole conversation is heartwarming. Asking about his/her dream and getting that loving and warm reply is something we all want and deserve.
This is the flirting that sweeps you off your feet. You just have to fall in love with this person. This is the kind of conversation that makes us want to fall in love for the first time all over again.
Cute-Detector
This is a conversation that will melt your heart. Both the people in this text exchange are on a full “flirty” mood. The back to back compliments would be pretty dumb and creepy if both of them weren’t on the same page.
The responses to those compliments could have been sarcastic but are not. Well, they are officially on the relationship lane – with all the flirting and all. We ship this!
Big Oops
He was caught red-handed! We can’t ever be sure if this was an honest keyboard prediction mistake or if this guy is actually cheating. Whichever it is, just to be safe, the girl should most definitely stay as far away as possible from that boy.
If this was a mistake, it will surely make him pay a great deal. This is why we keep saying: boys! Please always double or triple check what you text a girl!
Epic Failure
Well, that was some horrible texting. We cannot blame the girl for wanting to end him. Did he try to rap? Or was it a poem? Well, whatever it was, it was not effective in its intended purpose. The girl just wasn’t impressed.
We all want to end him for ruining the girl’s mood. He just has to up his game, and maybe he knows it. The message was in all caps, after all.
Reassure Her!
It is always important to ensure your financial security. We have to be pragmatic in all situations even if it ruins a completely sweet chain of messages whose proper ending would melt everyone’s heart.
As much as we are mad for ruining the moment, we are also very happy and proud of her for speaking what is in almost everyone’s mind. Assurance is what makes a relationship stronger – besides, of course, love.
Cookies Are Love
Poor jack just wanted some dirty talk. Too bad, his girl just doesn’t seem to be in the mood. We wonder if it’s just her random mood or if he had done something to cause this unfortunate exchange. No matter what, this girl will have her cookies, and who can blame her?
There could be nothing better than munching on some cookies while laying on your bed. Also, please charge your phone!
Broke Through Earth’s Crust
Well, this is one of the oldest tricks in the history of flirting. Sometimes, though, you just have to go to the old methods. Well, it seems that they definitely worked if they survived this time.
This boy added a little twist, though. It should have been heaven. That would make it the sweetest, but maybe he decided to add a modern edge. We do love fusion between old and new.
Was It an Indication?
Was it a brag? Or was it a joke? Or was it an invitation? – we can’t tell for sure. Whatever it was, it made us laugh and wonder. We think it started as a brag, which was shaped into a joke.
At least, she tried to make it some sort of a joke. It was not very successful, though. The guy is now just confused. Maybe it needed more enthusiasm from the other person. Who knows how it would have ended then?
Wedding Season
Yes, this guy’s got one thing right. The first step to marriage is definitely getting to know someone, but having said that, this is not something to say to a complete stranger who may or may not be a girl.
Even a known person would get creeped out with this stunt. You’re not even supposed to talk or write to strangers, didn’t your mom teach you that? How old are you?
Marry Him
We all need someone who will see a really cute dog and ask us if we need a picture. The answer will always be in the affirmative. We always need to see the picture of a really cute dog. That’s what keeps us going in life.
No – we are not exaggerating or overreacting. If you found someone like this, marry him/her immediately and send us a picture of the really cute dog.
Six Feet for the Win
Some people are biased towards taller people. At least this one right here is. The reply to the answer says it all. The girl asked the guy how tall he was and he took no time to reply. Maybe he wanted to brag too.
Well, he is more than six feet tall. Reece’s response might be the inner response of so many girls. From the response itself, we can conclude that she is amazed.
Smooth Flirting
In this crazy, universe even saying “okay” to someone can be interpreted as flirting. Does this conversation make it seem like they are a married couple or is it just me? We guess there are some things we can never know.
However, if this truly is a marriage, then we take our words back – it truly is flirting. We single people just have it hard. If they are not married, though, then that girl is plain weird.
Extremely Smooth Flirting
Some people just know how to flirt. Their flirting game is so high that, sometimes, it is hard to understand. That is the case in this one. It took the girl some time to understand what he meant.
We can relate to the girl too. This was some extreme level of smooth flirting. It could have been gone too creepy and funny very easily, but as we said earlier – some people just know how to flirt.
Fineapple or Dragon Fruit?
This is the perfect example of “flirting gone wrong.” This boy started with simple flirting. Well, you can never be too cautious, but it was not of any help. The girl finished his flirting game in seconds.
To be fair, his flirting game was fine, but the girl was on another level. She just wasn’t having any of it. She would be great dragon fruit indeed. Look at her reasoning!
The Real Deal
If this isn’t true love, then we don’t know what is! Who doesn’t want a guy who will peel tangerines for you? Marry this man and never leave his side. This reply has the perfect amount of humor and sweetness.
This reply would make anyone smile as it’s neither cringey, nor indifferent. This sure makes us curious to know what Chloe has to say. All we can say is, we ship them wholeheartedly.
You Just Can’t Compete
You should always ask a girl you like if she has a boyfriend. If the answer is positive, you need to ask and enquire about the boyfriend so that you can know if you have a chance.
In this particular case, the boy really doesn’t stand a chance against the boyfriend. It was a good thing he asked beforehand. Now, he won’t go compete and make a fool of himself.
Finish the Sentence
We should always finish a sentence both in verbal and written communication. Otherwise, things like this happen. This person’s straightforward question and the sarcastic reply surely made our day.
It was mostly fueled by the text that followed the sarcastic reply. We always need a bit of sarcasm and embarrassment in our life. It keeps us going, and we thank these two people for lighting up our day by a little bit.
No Pictures for You
Yeah, an empty hanger is exactly what you deserve and nothing more. Also, don’t you dare share her hanger with anyone, for it is deeply personal. Jokes aside, asking for explicit pictures from a girl is a punishable act if it has been coerced.
So, boys, please do keep this in mind before making such aggravating demands. On a much lighter note, the poor kid must have been very disappointed after receiving that picture.
Too Clueless
Sometimes, people can be quite clueless in conversations, but some people can be clueless to a point where it is so funny that we can’t resist getting a screenshot to share with everyone. This person’s refusal to understand what the other person can mean two things.
One – Yes, you guessed it: the person is clueless. Or, two – the person doesn’t want to understand what the other person wants to say. We’d lean towards the latter!
It Was a Hot Day!
Well, this man knows how to flirt. He knows how to connect the dots. He started by saying how much the day reminded him of her. Then he proceeded with an answer we were not expecting. The day was really hot, and you guys can connect the rest.
The answer actually made us laugh, though. We had to end our list with something goofy like this. After all, couples who laugh together stay together!
Please, Be My Sock
There is no greater longing than that of looking for your sock. Nothing can be more painful than not finding the pair to your sock. We can completely understand the genuineness behind this statement.
The best feeling in the world is that of finding your perfect pair. So, we hope this sweet boy really did find his other half with this unknown number girl. The anticipation of the reply from the girl is keeping us to the edge!
When Science Fails You
This is an interesting fact. Clouds look fluffy like cotton and float around in the sky. Anyone would assume they’re very light and nearly weightless. Well, clouds are actually made of millions of water droplets and, given the massive size of clouds, you can easily guess how heavy they might be.
So, yeah, remember to fact-check before you try to flirt with something scientific. Also, be careful who you flirt with!