31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

The world of modern dating can be cray-cray. More and more, people are turning to dating apps in the hopes of meeting their perfect match, but this doesn’t come without its pitfalls. With the ever-present hookup culture, unsolicited adult pics, catfishing, and profiles that use photoshopped images or filters, online dating is a potential minefield. 

One Reddit user recently turned to the community to ask the question, “People who use dating apps, what is the weirdest message you’ve gotten to start a conversation?”, and the results were truly mind blowing. Keep reading for 31 of the strangest messages online daters have sent as an icebreaker.

More info: Reddit

#1

Opened our initial conversation on PlentyofFish by asking for my detailed zombie apocalypse survival plan.

I fell in love immediately. We’ve been married for almost 12 years now.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: anon, cottonbro studio

#2

I once got an opening message that said something like “you might not be the prettiest girl on here, but beauty is only a light switch away.” This was over 10 years ago, and I bet that dude is still single.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: Crystaltornado, Tara Winstead

#3

My brother sent this girl a message on Hot or Not: “Do you like burittos?”

They’ve been together for 17 years and married for 11 now.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: Henry__Every, Pixabay

#4

A girl once messaged me with something along the lines of “do you ever see a bunch of cheese and say damn, I want to eat that cheese. And by cheese I mean my p***y”. I couldn’t help myself and replied that I’m lactose intolerant.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: Teazykatka, Engin Akyurt

#5

A friend got the message “Wow. Your eyes could start a cult”.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: pinkynarftroz, Noelle Otto

#6

The weirdest first message I’ve received was “My hovercraft is full of eels”, and I can’t imagine what sort of conversation she expects if the person she sends the message to doesn’t happen to be a Monty Python fan (we’re getting old and rare here).

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: malsomnus, Jeffry Surianto

#7

Matched with a woman. Her first message was, “I guess you’ll do.”.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: Bigt**s38, Charlotte May

#8

“I want my wife to have your eyes.”

I don’t think it was meant like that, but my first thought was that the dude wanted to cut out my eyeballs.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: CurvyCarrots, Noelle Otto

#9

I was the weird one. I’d start off commenting about something in the background of a pic. If I couldn’t think of something funny I’d just say “how do you feel about geese?” Most people have strong opinions.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: SomeS**ttyBean, Pixabay

#10

“Excuse me good sir, would you kindly like to hook up?”

She was clearly wasted. 5 minutes later she unmatches. Apparently she didn’t like I wasn’t available immediately. This isn’t a f*****g Wendy’s.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: FriendsForEternityLH, Andrea Piacquadio

#11

After my girlfriend and I started dating, she showed me her dating profile so I could see how many messages she was getting. About 50-70 per day, most of them were just “hi”. A few were really creepy (“you look like my daughter/student/sister”), but one stood out to us and we laugh about it to this day.

“you ever get f****d by a marine baby”

No punctuation or question mark, so we asked ourselves “what, like a baby shark? Baby whale?” lol… In the end she had 1500 unread messages when she deactivated her account.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: Soulfighter56, adiprayogo liemena

#12

I am a sterile man and a woman messaged me first on Tinder with “It’s a shame you can’t have kids. I mean, what if we fall in love after we f**k and I want to have your babies and I can’t? I’m sorry, I don’t think this is going to work.” After I replied, she ignored it and unmatched a few days later. We were both looking for casual so extra weird.

As a bonus, when I moved to a new area, I decided to use Bumble BFF to make friends. I didn’t realize that apparently gay dudes use it to low-key try to pick up straight men. The first message I got was a dude asking me if I would fart in his face with my cheeks spread open. I turned it off after.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: Wishilikedhugs, Pixabay

#13

Whose d**k do I have to suck to suck a d**k around here.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: Big-Carpenter7921, Maurício Mascaro

#14

As a man, I didn’t get any opening messages. Got some doozy responses. One that still haunts me is when I sent this woman a nice opening message, talking about some of the things in her profile we had in common and asking a few open ended questions to start a conversation.

Her response was: “With all the hot military guys in town, you need to put your aim lower.”

Then she blocked me. I thought I already had low self esteem, but it took another hit that day. lol.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: TypeGreen51, Rosemary Ketchum

#15

I was on hinge for a while and saw someone had “can’t text/call/meet on weekends because I’m in jail.” I thought this was a joke. It was not. She was doing time on the weekend for assault.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: Exobyter, RDNE Stock project

#16

Some gay dude offering me a free place to live if I s**t in a box and gave it to him every time I s**t.

I was neither gay nor looking for a place to live and I didn’t bother to ask what the s**t was for.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: BasicallyJustAnIdiot, Kim Stiver

#17

“You want to be my first dark skin ;)?”
Some gay dudes really have no shame.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: Karakara16, nappy

#18

“You’re cute , hate dogs though”

(I had very my cute dog in a photo).

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: DuffNinja, Helena Lopes

#19

I was on Bumble, and got asked my Myers Briggs personality type. When I responded, she unmatched immediately.

Gotta respect the hustle.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: chromane, mikoto.raw Photographer

#20

“WHY DON’T YOU SKYDIVE INTO THIS P***Y!!!” and then immediately unmatching me when I was like, “Woah now…”.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: Synamyn_Dyxon, Tom Fisk

#21

Ah man. There were a few.

“What is your credit score?” (literally their first line after I messaged a greeting)

“Do you want children? I want to start having them in the next year.” (this is coming from someone in their late twenties)

“I like it when people are mean to me. Can you f**k me up?” (that’s baggage I can’t handle even at the best of times)

“CNC?” (translates to “Consentual Non-Consentual”… hard no for me)

“You’re not my type. But my gay friend thinks you’d be a good ‘daddy.’ Can I give him your number?” (kinda flattering, I guess?)

“My husband died last year and I am looking for someone to be a part of my family.” (she had 3 kids, all sub 10 years old)

“You’re white. I only date black guys.” (so why’d you match with me???)

The list goes on. Needless to say, I periodically rage-quit dating apps after a month or two of this.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: Shahfluffers, RUN 4 FFWPU

#22

‘Hi there! You look like Anne Frank’ 🙁.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: Discotraxx1990, Photo Collection Anne Fra

#23

My ex got messaged by the Swiss Cheese Pervert on OK Cupid.

He started out respectful enough but by the 3rd paragraph was talking about how he likes to [enjoy some alone time] with cheese.

She told her friends but no one believed her (she blocked him so the messages disappeared) until he started [being a bit too intimate] with cheese in public, got caught and went viral.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: negativeyoda, NastyaSensei

#24

I matched with a guy who taught at my old HS. I was in his homeroom class for 1 year, so we didn’t really talk much, but he gave me an entire essay confessing his love to me. He told me how he noticed me but never made the move, and was glad I finally reciprocated.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: panfriedtomato, Andrea Piacquadio

#25

Whenever a girl starts a conversation too [intimately] or wants [intimate pics] right away, I know it’s a scam.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: jordan-lakers9394, Andrea Piacquadio

#26

I’ve been in a relationship for five years but I was regularly on Tinder before that.

I had my job title and company on my profile, which back then was an administrative/management job for a UK parcel company.

Girl messaged me asking if I could track her parcel for her. I didn’t know if she was joking or not but she just kept asking me weird things about parcels and then blocked me.

Forever wondered what was the point?

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: Jlaw118, Artem Podrez

#27

My buddy got a self-esteem slaughterer of a response once.

He asked her about the book series she mentioned in her profile.

She replied, “Too far. Too fat.”

And that was it. Killer.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: ThingCalledLight, Pixabay

#28

In 2016 I once got “Is your name Harambe? Because I want you to drag me around in public”.

Image source: unib**b_official

#29

One guy asked me for a pair of dirty panties.

One offered to make me dinner at his house and gave me the address.

One guy asked me if I would go with him to burning man.

A guy asked me how much I made an hour, because he wouldn’t date anyone who made less than 20 an hour.

Yet another asked me if I knew what BDSM was, and demanded that I be a submissive. (I am no where near submissive, except with one human being.)

I had pretty much given up on online dating for years, now.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: Di_Terces, Michael Burrows

#30

A woman on her first message, which was literally sent just to moan about how I was “in my 30’s and didn’t own my house”, like I could magically find a solution for that. That was all she messaged for, as far as I can tell.

Didn’t even bother to reply and tell her that I was renting because I’d given my house to my ex-wife rather than fight over it.

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: ledow, todd kent

#31

I had on my “about me” that I was an artist. She flew off the handle that I had a regular job as a sign designer. Called me “fake”. How about “responsible”?

#32

A girl matched with me and messaged me that “She’s older than me and men’s egos are very fragile”. No idea how she thought that was gonna go..? She was a year older….

31 Truly Strange And Hilariously Cringe First Messages From The Universe Of Dating Apps

Image source: fishsix, Becca Tapert

#33

heard one about someone who got asked do you eat p**sy and he responded with no only pork. lol

#34

Not me , but on Omegle (an old website were you basically FaceTime strangers) sooooooooo many old men showing their peepee to young girls.

#35

An old school friend DM’D me… “I see your surname changed [back].”

#36

This isn’t from a dating app, but one that I found.
“Are you Lebron James? Because you are my sunshine”