The Tinder Files – SCARIEST Dating Site Pickup Lines – October 2017

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Don’t worry , don’t worry. Yes, it’s almost Halloween so my dating site pickup line roundup is a little on the scary side. But fret not– I’ve still inserted my charming wit, as well as a few cute lines.

If anyone’s new here, you’re welcome to check out the long version of why I write these posts. If you want the short version, stick around, I’ll tell ya.

The Tinder Files are my attempt to hold people accountable for their dating site behavior. Technology has given us many gifts, and confidence is one of them, but sometimes it’s misused in online dating. People start to say things that they’d never say if they met a person in real life, and it can have an effect on the self-esteem of the person getting the messages. Trust me, I felt it. I was using at least one dating site every day over the course of several months, and I started to wonder why I was feeling so crappy. Turned out, the “compliments” I was getting were really wearing me down. Nobody was trying to get to know me, they were just sending me these really crude, sexual messages. Nobody would talk to anyone that way in a bar. They’d at least say hello before saying they wanted to fuck me up against the wall.

Yeah, it’s uncomfortable, isn’t it? It’s a little weird to say something like that in this context. You came to my site expecting something pleasant, and got something that put you just slightly on edge. Now imagine that happened to you every day for a year. You’d end up pretty on edge, yeah? That’s why I’m trying to change the way people talk to each other when they’re on a dating site. Just because there’s a screen between you doesn’t mean you can forget there’s a real person on the other end of those messages. They’re real, and they affect people.

So, here’s how this thing works. I post the cringeworthy, crude, inappropriate pickup lines because I hope they’ll make it less socially acceptable to treat people like sex objects. I post the ones that don’t make any sense, because I hope that even if you want someone just for casual sex, you’ll stop and proofread your damn message. Finally, I do make an effort to post the funny ones, and the clever ones. I don’t want this project to be all doom-and-gloom. I want you guys to laugh, too! Let’s be honest, most of these are really freakin’ funny.

So, there are a few rules I follow to make sure this doesn’t come across mean. And I hope if you comment, you’ll follow them as well. The first is that I never make fun of anyone’s race, ethnicity, or general appearance. I’d never do that anyway, but I wanted to make it clear for this. I’ll also never post about anyone in a negative way if they seemed to have good intentions. I know it’s hard to put yourself out there, and I’m not here to make it harder. Finally, I’ll block out any clearly identifying features, like closeup selfies or full names and locations together.

So, I think I’ve done all my talking, and we can finally get to the good stuff. Here’s the ~scary~ October roundup of the best and worst dating site pickup lines.

Dating Site etiquette is apparently quite different from traditional dating etiquette. In an attempt to change that, I'm posting the crude, inappropriate, and careless pickup lines men send me online. And let's face it, sometimes they're just really funny to read.


1. CuTe

The level of cheese in this pickup line is the scary part! But hey, I can always go for a cheesy pickup line, so it didn’t bother me!

Dating site etiquette is apparently quite different from traditional dating etiquette. In an attempt to change that, I'm posting the crude, inappropriate, and careless pickup lines men send me online. And let's face it, sometimes they're just really funny to read.

2. Hershey Factory

It’s scary to think of Hershey’s going out of business but I do very much appreciate this ~sweet~ line.

Dating site etiquette is apparently quite different from traditional dating etiquette. In an attempt to change that, I'm posting the crude, inappropriate, and careless pickup lines men send me online. And let's face it, sometimes they're just really funny to read.

3. Nice Boobs

This is just…scary. One of those that could get a drink tossed at you if you said it to the wrong girl at a bar. Yet, it’s tossed around this dating site (I think this one’s OKCupid) like “you’re pretty.”

Dating site etiquette is apparently quite different from traditional dating etiquette. In an attempt to change that, I'm posting the crude, inappropriate, and careless pickup lines men send me online. And let's face it, sometimes they're just really funny to read.

4. On Hold

This is a joke, right? Sent me a message to tell me his message is coming later?

Dating site etiquette is apparently quite different from traditional dating etiquette. In an attempt to change that, I'm posting the crude, inappropriate, and careless pickup lines men send me online. And let's face it, sometimes they're just really funny to read.

5. Roy G. Bob

Alright, so we’re halfway through, and it’s been a little scary what with the grossness and the thought of Hershey’s being gone…so I’ll show this one next. This gem is one of my all time favorites, so I hope it makes you smile, too.

Dating site etiquette is apparently quite different from traditional dating etiquette. In an attempt to change that, I'm posting the crude, inappropriate, and careless pickup lines men send me online. And let's face it, sometimes they're just really funny to read.

6. Smooth as an Oil Slick

Is this some sort of literary joke I missed? I hope so. Otherwise, someone’s trying waaaayy too hard with the B&W aesthetic and the guitar in the photo and speaking in the third person.

Dating site etiquette is apparently quite different from traditional dating etiquette. In an attempt to change that, I'm posting the crude, inappropriate, and careless pickup lines men send me online. And let's face it, sometimes they're just really funny to read.

7. Spank Your Butt

Aaaaand we’re back to the scary. Or at least the annoying.

Dating site etiquette is apparently quite different from traditional dating etiquette. In an attempt to change that, I'm posting the crude, inappropriate, and careless pickup lines men send me online. And let's face it, sometimes they're just really funny to read.

8. Holden Caulfield

The beginning of a literary masterpiece, this pickup line. I wrote my grad school entrance essay on this book. He didn’t even know, and he effectively wooed me.

Dating site etiquette is apparently quite different from traditional dating etiquette. In an attempt to change that, I'm posting the crude, inappropriate, and careless pickup lines men send me online. And let's face it, sometimes they're just really funny to read.

9. Want Ad

And back to scary. But I stared that monster in the face and was twice as witty. HAH.

Dating site etiquette is apparently quite different from traditional dating etiquette. In an attempt to change that, I'm posting the crude, inappropriate, and careless pickup lines men send me online. And let's face it, sometimes they're just really funny to read.

10. What Would Freud Say?

There’s always one that brings psychology into the mix. Disappointed. 2/10 would not smell hair.

Dating Site etiquette is apparently quite different from traditional dating etiquette. In an attempt to change that, I'm posting the crude, inappropriate, and careless pickup lines men send me online. And let's face it, sometimes they're just really funny to read.

What are your dating site HORROR STORIES? Share them in the comments below!

6 Comments

  1. OMG! I’m on a dating app sabbatical because I want to try meeting people ~organically~ 😛 but this is bringing back some serious memories! Your responses are hilarious!

    • Ugh, you’re smart! I think it’s time for me to cycle back to meeting people organically, too. I got myself a creeper who’s messaged me fifteen times and I haven’t answered any of them. Makes me want to go back to the old-fashioned way!

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