“Why Won’t You Talk???”: A Comprehensive Guide to Online Dating

When I graduated college, I was exasperated that 4,700 nights of greying out at the Palace hadn’t netted me a kind, handsome, brilliant husband with 2 corgis, a house in the Hamptons, and extensive knowledge of the alphabet trick. (3 years later, I am still not sure quite why this didn’t work? But I digress.) Out of this resentment, my OkCupid profile was born, and it has lived mostly-off-but-occasionally-on since.

Somehow, in the sea of “hi”, “i luv redheads ;)”, and “i fuk u plz?”, I met my truly wonderful boyfriend last November (awww). I learned from Cosmo that men only want what other men want, and to keep a man, he needs to know how lucky he is that you chose him over the literal thousands of other suitors at your online doorstep.

decent redhead

So for the first few months that we were dating, I left my profile up and showed him my favorite incoming missives. I think it was eye opening, as a man, to see what a woman’s online dating inbox really looks like. He was, to put it gently, taken aback. We’ve all seen sites like TinderNightmares, but at this point, it’s evident that most of those messages are carefully planned to get a reaction, reused so many times that they’ve lost all meaning, or just incredibly fucking fake:


Thank you for taking 15 seconds to copy that from PeacocksGetLadiez.com and paste it into my inbox. A true pleasure for all involved parties.

Therefore, I reactivated my profile last week to get some strange… I mean… screencaps! To get some screencaps!… to use in this post. All of the following are taken directly from my inbox- 100% real, manipulated only to cross out the identities of the accused (most of whom don’t deserve it).

Online dating is a nervewracking experience. “Which pictures should I post?”, you think. “If I’m into someone, should I message them first??” “What if no one likes me???” In truth, online dating is easy! To demonstrate just how easy, I’ve put together a quick-and-dirty guide (just how you like it!) that will essentially guarantee your success.

The Official Carly’s Into That Guide to Online Dating

1. Don’t do this.


Real talk: this was the first message I ever received on OkCupid. Clearly, because I was naïve enough to respond with “sure, random stranger, ask me a ‘weird question’! I bet it’s not going to be about your dick!” Alas: it was about his dick.

2. Don’t do this.


Thank you, as well, for sharing a beautiful pic! Of your crotch! In a pair of Express jeans!

3. Don’t do this.

wanna get breakfastbrandon to usealternate 1

This last guy is my favorite. “You ok over there?” No!! Help!!!!! The only possible reason I wouldn’t have responded to your 4 messages in 1 hour is because I’ve been involved in a terrible accident where I have lost my hands and/or eyeballs and/or ability to speak into my iPhone’s voice-to-text function! It definitely isn’t because your profile looks like this!



sobbing gif

Extra-special bonus points for this part:



4. Don’t do this.

domination 2

I feel like you should GO TO JAIL?

Having apparently not found a woman on the internet who was willing to converse about and/or partake in “domination and rape roleplay” with him (PREPOSTEROUS!), this relentless charmer was back 6 months later with a brand new username and some horrific new verbiage:

domination 1

a) I’m telling you, especially, to die in a fire.
b) I can’t wait to make you go to jail. Are you in jail yet? You are, right?
c) Using the word “whim” in a sext is almost as offensive as the rest of this rapey-ass shit. This isn’t an AP exam, you fucking weirdo.
d) For this portion, I made a helpful Venn diagram about penises:

5. Don’t do this.

pretty toes


6. Don’t do this.

willing to bet

This fecal sample messaged me again, a few months later, to say “can we start over?”

YES! We CAN start over! My silly lil girlbrain has already forgotten that you first contacted me with a vulgar question regarding my skills at performing oral sex. Speaking of oral sex, I MUST PROVE MYSELF TO YOU IMMEDIATELY! REMOVE YOUR PANTS!

7. Don’t do this.

nice make up

Thank you! I use it to trick innocent, unsuspecting men into thinking I’m attractive. Also, Merry Christmas!

8. Don’t do this.

tongue legs

Just like that, huh?


9. Don’t do this.

first richard

I’ve received this message several times, from several different usernames, over the course of 2 years. Several of my female friends have also received this message, on multiple dating apps, from several different usernames, at varying points on the 2-year time continuum. BRUH! IT’S TIME TO TRY SOMETHING ELSE! (perhaps, even, something less vaguely pedophilic? just spitballing here.) So this time, I decided to see what would happen if I gave him the answer he was looking for.

trouble 1


Turns out, I’m not exactly Richard’s type!

trouble 22   trouble 44

When I reactivated my profile for this post, I knew I was signing up for some shit. But I never in my WILDEST DREAMS would have thought that someone- a someone who is also on a dating site, for people who are single and want to go on dates- would send me a message that says “Lonely people seem to flock together like poor people do, so they can feel better about their plight.”


Y’all, this was fucking Christmas. I am more #blessed than I could ever deserve.


can u not

Can anyone guess what’s behind doors 1 and 2 of the first and only message I ever received from this individual?

My dear bepenised readers, should any of you exist: do not, EVER, under any circumstance, send a dick pic to a woman who has not expressly requested or consented to receiving a dick pic. If a woman wants to see your dick, YOU WILL KNOW. We are just about as subtle as y’all are. Common examples of things a woman might say if she wants to see your dick:

-“Hey, can I see your dick?”

-“Mmmm, show me your dick ;)”

show me

Until something of that nature occurs, your assumption MUST ALWAYS BE: “this woman would not like to see my dick today.” For some, this is a tough concept to wrap one’s head (HEYO!) around. But a woman’s very existence on the internet- even on a dating site!- does not mean she would like to see your dick, or that you should send her pictures like this, just in case she wants to see a random stranger’s weird erection at 9am on a Wednesday morning but is too shy to ask (censored, but still NSFL):


Nice hoodie, Santa! Keep it on, put on some goddamn pants, take a cold shower, and you’re all set!

Reader, take heart: your soulmate is out there. If you follow the above instructions carefully, you, too, can date online like a motherfucking champion. Find the other half of your heart, and woo him/her with a carefully crafted message about their interests, hobbies, career, BDSM preferences, feet, blowjob skills, and/or availability to hang out at that very minute.

On the other hand, maybe you shouldn’t take it from me. I don’t really know what I’m doing.


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