25 Women Reveal The Weirdest Opening Messages They’ve Gotten On Online Dating Sites

Online dating is a weird, weird world. You have to have a trifecta of good photos, a great bio, and killer conversational skills to separate yourself from the teeming masses. Recently, a guy friend of mine was bemoaning how many messages girls “must have in their inboxes,” and because quantity does not always mean quality, I asked my friends and Twitter followers (thanks, ladies!) for the most creative ways strangers have ever initiated conversation.

1. Kelly, 23

2. Anne, 25

I had a guy once who messaged me on Tinder, saying that I had been entered to win the ‘Tinder Slut of the Month’ contest, sponsored by Victoria’s Secret, and judged by him. The categories were best blow job, best titty-fuck,and best sex. I blocked him immediately.

Like, I know Tinder is not the classiest way to meet people, but I’m not about that.

3. Brit, 28

“damn girl, you so cute, I just wanna douse you in green paint and spank you like a disobedient avocado.”

4. Ashley, 29


5. Steph, 22

A 46 year-old man once sent me, “hey whats up…… whats your favorite position…lol”

6. Cassandra, 20


7. Virginia, 28

“I am guessing that you get mostly guys with pictures of abs or hiking or talking dirty and wanting your phone number to send penis pictures?”

8. Annie, 29


9. Molly, 31

“What I have in mind for our date is simply meeting up at a park… something low-key so that you can run away in 10 minutes if you want to without any pressure.”

10. Carolyn, 27

My favorite is when guys send “Would you be up for chatting some more?” as their way to start a conversation. Don’t you have to have been chatting to begin with to chat some more?

11. Bree, 23

“Let me give it to you straight. I’d like to chat but I am not going to get excited about someone that I have not met. I understand that there are some asshats on here so I appreciate the risk you are taking if you respond.”

12. Heather, 26

“replies very selectively . ..” meh.. . guess I will make this short than..”

13. Jane, 20

“If you weren’t so far away I’d have you sit on my face while you choke me”

14. Lindsey, 30


15. Sophie, 22

“Apologies for the forwardness, I couldn’t help but notice how pretty you are and thought maybe I might be able to offer you a unique experience in a calm discreet environment.

I’m talking about you the center of attention for multiple men all focused on your pleasure. If its not for you, its ok. But if you are, feel free to respond back to me”

16. Amanda, 23

“Hello witty person! I feel a bit silly for messaging because I live half way across the globe from you, but I was too weak not to do it. I wish I had a better excuse than telling you how lovely and intriguing you seem even from afar. A better excuse would be what men sometimes do if a wonderful girl makes their knees wobbly. They press them agains a wall and kiss them, while pretending it is some kind of act of passion. In reality it was the only way not to look like a complete fool and fall down when she turned his legs into pudding, so kissing against a wall is a perfect excuse.
I will get back to you if I can think of something similarly clever.

Take wonderful care,l”

17. Tyler, 24

“You’re adorable, so adorable in fact that I’ve decided I’m going to adopt you as my
new little sister! Don’t worry, we’ll spend all our time climbing trees and drinking kool-aid.
Actually you seem like a cool person, I’d love to get together sometime and let you cook for me haha..
Wait! You’re not crazy, are you!?”

Editor’s note: I received this exact message, spacing and all, from three separate women. THREE.

18. Sarah, 21

“Not bad. Could use a little Photoshop”

19. Nicole, 26

“You probably hear this every day of your life, but you are incredibly beautiful. I’m slightly baffled. Women here don’t compare. I worked hard on my profile, so I hope someone enjoys it. It should give you some insight on if we would get along.

I didn’t want you to think I was only messaging you because of how you look so I read your profile too. It seems like we would get along perfectly. I have a good sense of humor, like probably the best sense of humor ever and you seem like you can enjoy that in someone so here I am writing a long long message to you and I’m rambling now. I have a habit of rambling, sorry, it happens when I’m nervous.

There is no question that initially I was drawn to your profile because of your beauty, but I do want you to know that I know there is more to you than that, so I want to know more. I want to see if the “interior” matches the “exterior” if you will. Sounds a little creepy when I say it that way, like I’m going to cut you up and look at your insides…ummm. What I mean is, I just want to see if your personality is as gorgeous as your face. That’s what I’m saying. I should probably go delete the part where I’m talking about cutting you up, but it takes too long to delete. Oops.

Regardless, I’m [redacted] and you are incredible. I’ll be having my fingers crossed waiting for a reply from you. *crosses fingers*”

20. Shauna, 24

“DAMN MINNIE CUTE AS HELL. step up she make you look beat” – my profile picture was me with Minnie Mouse at Disneyland.

21. Ashley, 27

This was all from one man:

“I know, this looks like a total spam message, but hey – it’s the best I can do.

Congratulations, you came up in my matches!!!!!!! I know right, you’ve been waiting for it! You can call everyone, let them know. Tell your friends about it. You’ll have to girl talk for at least five hours tomorrow about it. I mean, what are the chances!

Ok, so I like to laugh and make everything into a sarcastic joke. It happens, right?

Now. I could write a resume. Tell you all about me. Like I am applying for the position of the guy you are going to hang out with on Friday, or whatever. But that would be boring and dull. I might fall asleep doing that.

Wait, I could list out interrogation questions! Ask you things like what you do for fun? or maybe something really deep… something like. “So where are you from?” You’d swoon, realizing that I care about where you are from and thus ‘where you’re coming from’. You’d get “all a flush” at my wit, right?

Oh, I know, I could just delete all of this and type “Hey wazzup? Saw your profile. Ur cute! hit me back and we can chat” That would probably work best. I mean, that’s what everyone does right? So it MUST work! Shouldn’t it?

How about instead, I do this. I am intrigued by your profile, and think it could be worthwhile to find out more about you. You know, talk, and answer those age old questions, like:

“Is she a total basket case in hiding?”
“Will I fall asleep sitting next to her when we hang out?”
and don’t forget…
“Is she just a guy with fake pictures, pretending to be a girl?!?!?”

So lets interact! Sound good? Glad to hear it! Lets get creative…

WE’RE GOING ON A ROADTRIP!!!! So where are we going and why?”

22. Ali, 30

This one’s my absolute favorite: “Hey, how was your night? oh and how i would love yo take you out into the country and bend you over my mustang”

Such a casual plot twist!

23. Marie, 26

“Hey what’s up? I’m [redacted]. Visiting LA for a couple days because I work in the NBA for a team. I liked your pictures and would love to talk. I’ll be straight up and saying im looking for sex. Hope you have a great night and day tomorrow.”

24. Cara, 28

“Your hair is fucking adorable! when are you going to ask me out?!!?


I think the last time I had adorable hair was the pigtail phase I went through when I was 5.

25. Kira, 26

This is always the classic:

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featured image – Sex And The City

About the author

Ella Ceron

Writer. Editor. Twitter-er. Instagrammer. Coffee drinker. (Okay, mostly that last one.)

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