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12 Awkward Dating App Encounters You Can't Avoid

12 Awkward Dating App Encounters You Can't Avoid

12 Awkward Dating App Encounters You Can't Avoid

Why doesn't anybody start a conversation with a simple "hello"?


Dating apps are a wild place

12 Awkward Dating App Encounters You Can't Avoid


When online dating first started, it seemed there was genuine interest in meeting people online, getting to know them prior to actually meeting them in person, and then going out on a date or a meetup to see how the vibe went from there.

While that can still (sometimes) happen, it's likely you'll get caught up in the jungle, especially if you're newer to the online dating world.

Here are 12 awkward and uncomfortable situations you'll probably have to deal with as you sort through all the fish in the sea.

1. The blank profile

blank grindr profile convo

I will never understand how people think they’ll get very far without having any kind of picture. Their profiles also usually say they won’t talk to you unless you have a picture yourself, and they usually start the conversation by asking you for more pictures.

2. The expiring photos

expiring grindr photos

This is right under the blank profile, because, even if they do send you pictures, they’re usually either blurry, of something totally random, or of just their body parts. Whether you like what you see or not, you only have a few seconds to make a judgment, and that can be really uncomfortable.

3. Starting something over nothing

grindr argument over nothing

Just because I don’t like you doesn’t mean it’s anything personal.

4. Oversharing

tinder conversation oversharing

It’s nice to get to know people, and it’s nice to get to know them in a timely manner, but at the same time, sharing is not always caring. Leave a little mystery, and save some of the oversharing for when we actually meet up.

5. Falling in love on the first "hello"

tinder conversation falling in love

Before we’ve even met? Really? Thanks for the interest, but… I mean… Before we’ve even met you’re in love? Sometimes people look great in their pictures, for sure, but know the difference between love and infatuation and do your best to keep calm until you’ve at least had a chance to interact.

6. Prying too much

tinder conversation prying too much

We’ve already talked a little about the oversharing, but it also goes in line with prying too much too fast as well. I don’t need to share everything about my life with you in the first sentence, either.

7. The never-ending list of what they are and aren't "into"

list of things he is and isn't into

Yes, we get it, you’re choosy. It’s really uncomfortable when you pull out the laundry list of things you are and aren’t into. Of course, it’s fine to have your preferences, and it’s totally okay to want to explore and play around in the bedroom. Sometimes, it’s just a little offensive, and it oftentimes goes in line with certain stigmas we as a community are trying to move away from. Know your audience and try to be respectful if things you’re into don’t align.

8. Starting a conversation with "looking" or "into"

Starting a conversation with "looking" or "into"

Hello? How are you? Nice to meet you? Anything? I get it that we live in a society of instant gratification, but it’s not really likely you would do this to someone when you first meet them at a bar, would you? You might get to it quick, sure, and I’m not necessarily saying there’s anything wrong with that… But a hello, at least, would be nice.

9. Starting with a dick or ass pic

starting with an ass pic

​Listen, I’m all for some nudes, send them my way. But, similar to the above, beginning a conversation as such without so much as an acknowledgment can be really uncomfortable. Even if we met at a nude party, I’d likely be able to at least see your face first, and even if that was covered, there’s still something to say about the energy of a person. Send a face before you send a body part.

10. No response is a response

no response is a response

I understand both sides of this one, to be honest. Sometimes, it’s annoying when someone doesn’t either just block you or tell you they’re not interested. That said, either way, you look sad and desperate if you just keep trying (I’ve been there, I’m calling my own self out). In the same line, if all you’re doing is saying “hey” and nothing else, and if your profile is totally blank, you may also want to consider a different approach.

11. Getting catfished

tinder catfishing

Even with a TV show exploring what makes people do this, I will never understand what makes people do this (unless you’re on Netflix’s The Circle and it’s implied that there are some catfishes around and it’s all about money and not real emotions.) Just… don’t do this, because it’s awkward, it’s uncomfortable, and sometimes, it’s also downright mean

12. Getting ghosted or blocked

getting ghosted or blocked

Being ghosted really sucks. It also sucks when they ask you for a picture, you send it, and they block you. These are inevitable when it comes to online dating, but sometimes, they hurt the worst. Especially if you get ready for the date and you’re there and they never show. There’s no knowing why people do it, but in the end, just like all of these other uncomfortable situations, all it will ultimately do is bring you closer to who you’re actually supposed to be with.

30 Years of Out100Out / Advocate Magazine - Jonathan Groff and Wayne Brady

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Andrew J. Stillman

Contributing Writer for

Andrew J. Stillman is a freelance writer and yoga instructor exploring the world. Check him out at or follow him @andrewjstillman on all the things.

Andrew J. Stillman is a freelance writer and yoga instructor exploring the world. Check him out at or follow him @andrewjstillman on all the things.