19 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.

Image credits: anon

#2

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).

Image credits: malsomnus

#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.

Image credits: Henry__Every

#4

“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.

Image credits: CurvyCarrots

#5

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.

Image credits: panfriedtomato

#6

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

Image credits: jordan-lakers9394

#7

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.

Image credits: Crystaltornado

#8

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

Image credits: pinkynarftroz

#9

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.

Image credits: TypeGreen51

#10

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.

Image credits: Exobyter

#11

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

Image credits: Karakara16

#12

"You're cute , hate dogs though"

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

Image credits: DuffNinja

#13

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

Gotta respect the hustle.

Image credits: chromane

#14

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

Image credits: Discotraxx1990

#15

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.

Image credits: negativeyoda

#16

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?

Image credits: Jlaw118

#17

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.

Image credits: ThingCalledLight

#18

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.

Image credits: ledow

#19

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….

Image credits: fishsix