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!

Leave a Comment