20+ People Who Asked for Way Too Much on Dating Apps and Made Everyone Uncomfortable

Sometimes, a dating app is a great way to meet new people and maybe even find your next relationship! However, it seems like a lot more of these conversations are awkward or even upsetting rather than endearing. From pick-up lines not being entertained to comments that should have never seen the “send” button, these are some of the most unexpected and unfortunate experiences on dating apps.

Riveting Conversation

It’s not easy to strike up a conversation with strangers. There’s a lot of small talk that can come with getting to know someone. Apparently, for this person, a little feedback was too much to ask.

Riveting Conversation

Instead, they were left with lackluster answers that didn’t really help them learn anything new about their conversation partner from these questions. If you were wondering, they didn’t know what their favorite movie was either.

The Whole Pickup Line

If you’re on a dating app, you probably hear a number of different pick-up lines. However, they don’t always work as well as you might want them to.

The Whole Pickup Line

This person really botched the one they were going with. Maybe it was for comedic effect but either way, we’re left wondering what they were going for in the first place. Either way, it doesn’t seem like this one worked out.

To Know a Name

When you start talking to someone on a dating app, you probably don’t expect to know much about them. However, some of it is given.

To Know a Name

For example, if you look to the top of your conversation, you’ll see the name of the person you’re talking to. It seems like this person could have used a slight review of who they were talking to. As it is, calling someone the completely wrong name isn’t usually a great start.

And Humble Too

Sometimes, the problem is that people on dating apps can come on a little strong. Take this Tinder user, for example. They managed to come across as both cocky and self-pitying – impressive.

And Humble Too

Not everyone finds success on dating apps, and that could just be due to bad luck. From this conversation, though, we’re not sure this person’s charm was quite up to the test. Also, who are they complaining to? This seems like a weird complaint to throw at a new match!

Asking More Than the App Allows

If you haven’t used Bumble before, it tries to shake things up with a unique feature. When you match with someone, only women can send the first message.

Asking More Than the App Allows

That’s why this guy was so confused about the fact that he had no way of messaging the OP when they matched. On the bright side, this was one dating app user who was ready to realize their mistake. The conversation could still be saved!

That’s Quite an Opener

Listen, is “hi” or “hey” your best opener when you’re trying to get someone’s attention on a dating app? No, it probably isn’t.

That's Quite an Opener

However, this response to someone saying “hi” is definitely worse than the original message. All in one message, this person manages to start out sounding pretentious and then horrifically tries to still flirt. All in all, it’s memorable for all the wrong reasons. We think we’d run from this conversation, too.

Waiting for the Perfect Moment

When you want someone to feel like you’re paying attention to them through text, a lot of people look for prompt responses. On the other hand, sometimes people get busy.

Waiting for the Perfect Moment

Still, you’d think the window of opportunity would close after two years. As for this person, they were pretty convinced they still had a chance to win the other person over – even if they did wait two years to shoot their shot.

Not Hearing Them Out

The first message you send on a dating app can be nerve-wracking. After all, you want to impress the person enough to get them to keep talking to you, right?

Not Hearing Them Out

Whatever this person thought the best joke would be, we’ll never know. It seems that asking this woman was too much, though we’re sure a simple “no” would have sufficed in place of this roast out of left field. Poor Jamie.

It’s Hard to Keep a Conversation Going

Small talk isn’t always easy to keep going. Unfortunately, this can mean that the beginning of a conversation on a dating app can prove challenging.

It's Hard to Keep a Conversation Going

This exchange seems doomed almost from the start. However, one person was really trying to get more information, despite the single-word responses. We wonder if the other person even thought twice about the guess after they received the message.

Is This a Threat?

A fun question can be a great icebreaker on a dating app. You’ll want to choose the right icebreaker question for the best effect, though.

Is This a Threat?

This question definitely wasn’t the right one. Rather than a light-hearted question, they opted for a rather grim one that not many people want to consider. Plus, who’s going to choose someone who just messaged them for the first time over their cat?

Do They, Though?

This person managed to get as far as landing a date before they ultimately ruined it. All they had to do was make it until seven o’clock tomorrow.

Do They, Though?

Instead of doing that, they managed to ruin it all right away. A good rule of thumb, it’s completely inappropriate to try and dictate how your date dresses. No matter what the last message says, we’re not so sure that this person is really a hit on first – or consecutive – dates.

Not the Best Option

A lot of people want to experience their own great love story. Why not look to classic literature for inspiration on what this could look like? There are some pieces of literature you might want to skip out on.

Not the Best Option

Finding the Romeo to your Juliet is a lot different if you remember the end of that play. As a matter of fact, even before this brutal end, it’s not a fun path for the two lovers.

Wow, What a Catch

We’ve said it before and we’ll say it again – the first impression you make on a dating app can really play a role in whether you get a message back. This person really failed on that front.

Wow, What a Catch

For one, they went straight past “coming on strong” and defaulted straight to being aggressive and demanding. The multiple messages with no reply really highlight how welcome this strategy is. Pro tip? Try and do the opposite of everything you see here.

And They Say Romance Is Dead

There are some who say you can’t find romance on a dating app. Well, you probably aren’t going to find it with this person. There’s a lot to unpack here.

And They Say Romance Is Dead

First, the other person obviously thought they were being asked on a date, not used. Secondly, it seems like a major red flag that someone wants their first date with you to be to bother their ex at their place of employment!

Um, No Thanks

Scheduling a date isn’t always easy. After all, it takes some coordinating to get two people together with differing schedules. Sometimes, something casual makes things a lot easier to schedule.

Um, No Thanks

Yet, this person might have gone a little overboard in how casual they were. Sending an address to hang out at their place was fine but requesting they arrive with coffee seems like a bit much and the tone doesn’t make it seem like they’re interested in hanging out with the other person at all.

No Need to Be Original

Having a go-to line is one thing. When you’re using a dating app, though, you might end up matching with people who know each other.

No Need to Be Original

That means when this person had their usual spiel lined up, it didn’t quite work as well this time. Why? Well, it might have had a better chance if this person and their roommate didn’t receive the same thing at nearly the same time. It just doesn’t make you feel as special.

It Was Only a Few Dates!

Going on a date doesn’t necessarily mean you’re “dating.” A lot of people take a while to get to know each other before making it official. This person may have misread the situation a bit.

It Was Only a Few Dates!

The first message comes off as accusatory, rather than trying to figure out the status of things between them. However, how was this person to know they were meant to have Valentine’s Day plans without mention and so shortly after they met?

I’m Sorry, What?!

When you ask for someone’s number on Tinder or any other dating app, you have to be prepared that they’ll say no too.

I'm Sorry, What?!

After all, it’s their right not to jump off the app and give you personal information right away or at any point. This person’s rule isn’t even that unreasonable – they didn’t know each other yet. The message in return was unpredictable and truly unnecessary. Who says something like this?

A Bit Presumptuous

There are some things that make sense to ask a dating app match you want to get to know better. For example, ask them to breakfast!

A Bit Presumptuous

This person didn’t quite land that idea. It doesn’t have the same effect to ask someone you haven’t met to just buy you breakfast for your own personal gain. We have to wonder if this person ended up matching with anyone who bought them that UberEats.

Asked Too Much

Have you heard the phrase “bit off more than you can chew?” That might be what happened here although this person definitely got a choice.

Asked Too Much

We can’t blame them for skipping past the pickup lines, those are rather abundant on these types of apps. However, it seems like this fact wasn’t as fun as they were hoping. Maybe the recipe is the way to go with this one?

With Conditions

Why do people date around? Maybe they want to meet new people or perhaps they’re playing the field and looking for love. Alternatively, maybe they’re just fishing around for new Instagram followers.

With Conditions

This can’t be a very effective method, though. Listen, if you want to charm people into liking you, making it clear your relationship is actually transactional for social media attention usually isn’t the way to go.

Maybe This Reaction Is a Little Strong

Do you remember when you were younger and learned about internet safety? Those tips can be useful but, sometimes, people use their full names on the internet.

Maybe This Reaction Is a Little Strong

While you may not want to do it personally, this person’s reaction is a little strong, to say the least. It’s probably not big enough of a deal – or at least an issue a stranger has enough say in – to demand they make a new profile like this.

Wow, What a Charmer

There are some things you just aren’t entitled to at any point. What this person is demanding is definitely one of them. It’s also inappropriate for a number of different reasons.

Wow, What a Charmer

For instance, it seems clear that the other person really wanted to get to know John before he decided to make such a foul comment in response to being asked out. We’re going to guess that this technique doesn’t make many people fond of this dude.

Why Message Them at All?

If you accidentally match with someone you don’t find attractive, there’s good news. You can unmatch them or simply not message them at all.

Why Message Them at All?

Someone should tell this person that. After all, it means that nothing is forcing you to be mean to the people you match with. What was even the point of sending such a cruel message to someone who had the audacity to like your profile? What a catch.

Is it So Hard to Believe?

There are some things you feel like you shouldn’t have to explain. This conversation is pretty clear on what’s so unpleasant about it. This woman added a profile picture to show a passion of hers.

Is it So Hard to Believe?

It’s something we all do. The audacity to message her and insist a father or ex-husband must have purchased it is more than just a bad way to open a romantic conversation – it’s downright offensive to brush her off like this!

That’s a Long Drive

Sometimes, it seems like people use dating apps for errands rather than romance. We can see why most people would be taken aback by it too.

That's a Long Drive

Asking someone to run an errand for you right away after your first message is already a bit presumptuous. However, this person wasn’t even just asking for a run to the store or a ride to the post office. We wonder if anyone else took them up on this five-hour round-trip ride…

Getting to Know You

This person really seemed to miss the point of messaging back and forth on Bumble. At the very least, we’re not sure what they wanted to talk about.

Getting to Know You

Asking someone what they do for a living or what they study are a few basic questions to get to know them. Rosemary didn’t seem open to it, though. In fact, she was quick to question why this person wanted to know anything about her at all. We wonder what would have been a more appropriate conversation matter in her eyes…

Oh, Thanks

There are some things people say and you have to wonder what they were thinking. Isn’t the rule if you have anything nice to say, don’t say anything at all?

Oh, Thanks

This person even seemed like they were hopeful for a good conversation – they started off with a compliment and everything! It didn’t take long for their match to reply with a rather brutal answer. Maybe next time a compliment might go well instead of calling the other person ugly.

A Lot to Ask

The first date with someone can be exciting. It can be the start of something new or just the chance to meet a new person.

A Lot to Ask

Since they’re not in a romantic relationship just yet, not everyone pulls out all the bells and whistles for a first date. That isn’t to say that a fancy first date isn’t memorable but not everyone is going to want to spend a lot of money just because someone demanded it from the start.

Well, They’re Honest

Let’s be honest, the idea of being spoiled is appealing to many people. Who wouldn’t want a little spoiling from time to time?

Well, They're Honest

As far as first messages on a dating app go, though, we can see why this one didn’t quite work out. They weren’t even asking for a fancy dinner, they were just outright asking for gifts from someone who they had only recently started speaking to!

Um, Okay Then

If you’re constantly getting asked how tall you are, it makes sense you might put it in your bio. Who wants to answer the same question a hundred times?

Um, Okay Then

As it turns out, that still doesn’t stop the unnecessarily disappointed reactions that come with this information. This person really takes the cake, though. What’s the point in matching with someone and messaging them only to let them know directly that they’re not your type?

Can’t Carry it Anymore

We know how hard it is to keep up a conversation on a dating app. After all, you’re basically trying to hold a text conversation with an absolute stranger. Needless to say, one-word responses only take the conversation so far.

Can't Carry it Anymore

The other person needs – and likely wants – your input in your answers and contributing to the conversation. We can’t blame this person for feeling like they were carrying the conversation at this point.

That’s One Way to Do It

This one is efficient, we guess, but not exactly the personal touch that most people are looking for when they jump online to find romance.

That's One Way to Do It

Not to mention, it’s a lot more time-consuming and impersonal to have to fill out a Google form before you can talk to someone. On top of that, this isn’t even the whole thing. It goes on for pages asking why you swiped on them, first date ideas, personality questions, and a final question of whether they’d ask out the writer after the survey.

Good Luck

It seems like there’s no way to stop the creepy messages that can roll in once you hand over your phone number to the wrong person on a dating app. We have to hand it to this person.

Good Luck

While they’re asking their potential date to take a risk here, we’re sure it’ll mean that their first message will be a little more thoughtful than it might have been. Although, we can’t think of anything more awkward than accidentally flirting with their father.

Is it Really That Hard?

First conversations can be awkward even for the most compatible pair. It takes time to get to know someone and learn about them. It takes less time to check the top of the screen and see the name of the person you’re talking to.

Is it Really That Hard?

In this person’s defense, it seems like they may have actually been trying their best but their keyboard just wasn’t cooperating. Still, it stopped this conversation before it even started.

Maybe it Wasn’t Funny

It isn’t easy to come up with a funny joke on a dating app. Right away, you don’t know your audience well, making it much harder. Izzy clearly didn’t find the joke funny or she just didn’t get it.

Maybe it Wasn't Funny

Instead, she was quick to correct the dude’s spelling, as if she really needed to make sure he knew how to spell “busy.” As it stands, the crude joke fell flat.

That Answers That

If you figure out something clever to say, you probably hope that your conversation partner will appreciate it. As a matter of fact, the wrong pickup line won’t just be off-putting – it might ruin your chances!

That Answers That

With a cheesy pick-up line and an unwilling recipient, it can be hard to get a conversation going. Perhaps Sarah here was just going along with the joke, which is why she chose to leave out the ‘Y’ in “hey” – otherwise, it seems unlikely that these two would even match in the first place.

Wait, Are You Serious?

It seems there’s a theme here with some of these Tinder matches wanting to control how strangers look. This isn’t fair to a new acquaintance or a long-time confidante, though.

Wait, Are You Serious?

These two seemed to hit it off well – well enough to exchange numbers. Yet, it all fell flat when one person made a big ask of another. We’re going to guess that this dude didn’t decide to grow a beard to impress people on Tinder, so why would he shave it for a stranger? Is it too late to swipe left?

Constructive Criticism

Once again we have to say, if someone isn’t interested in someone else, why would they match with them just to complain?

Constructive Criticism

We do wonder what this person’s picture was that their match found so offensive and off-putting. It didn’t take long for them to fire back. We have to say, being called a “meanie” isn’t something we expected between two adults but we can see why it works here.

You Could Just Unmatch Next Time

Tinder has a great feature if you make a mistake. All you have to do is unmatch the people you don’t like or didn’t mean to match with, in the first place. This will help take rough experiences like this off of the table right away.

You Could Just Unmatch Next Time

We wonder why this person didn’t just unmatch this person or simply not respond to their message. Messaging back to tell them they aren’t what you’re looking for seems like an extra, unnecessary step either way.

Oh Wow, This One’s Worse

Okay, while the last one was harsh, we suppose a message to the effect of “I didn’t mean to match with you” isn’t the harshest thing you could receive.

Oh Wow, This One's Worse

This one might be in the running, though. First of all, few people want to be told they were matched with as a joke. In addition, they probably don’t want to be point-blank called ugly either. Maybe not doing this at all would have been kinder.

This Line Isn’t Going to Work

There are some things that you just shouldn’t say in a conversation. Sometimes, you live and learn but that’s not what this person did.

This Line Isn't Going to Work

Even after they were told the joke was offensive and they shouldn’t say that, they only doubled down. We could go on and say that the “joke” here was ill-put, to say the least, but maybe it’s best that this person reviews their humor before trying out another “punchline” with any other matches.

Stay Focused

Asking someone about their interests or their studies is a great way to get to know a person. On the other hand, the same questions can get dull after a while.

Stay Focused

So, this person wasn’t too offended it seems when they were prompted for a more interesting icebreaker. The only problem is that this person managed to drop the ball on their new questions. Although we’re curious as to what happened with the kiwi!

What’s Going On?

There are some things that you don’t expect someone to start off with when you ask them a question. This exchange went from a casual icebreaker to a sudden, weirder conversation.

What's Going On?

The fact that this person messaged so many times about it really makes it seem like they want to talk about it. Not to mention, the demand to “earn their trust” only makes the situation more confusing. What do they want them to do?

A Little Personal

Pictures of someone are one thing you shouldn’t really demand upon the first message. It’s not really the only thing you shouldn’t demand, though.

A Little Personal

Do we really need to break down why this comment was so inappropriate? For one, it’s the first message in their conversation and this person jumped right in with a pretty offensive demand. All in all, they should probably make a trip back to the drawing board on openers.


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