Stories from the online dating trenches

It’s bad out there. If you’re in a relationship, you may want to double think breaking up. If you’re single, don’t put yourself in the online dating trenches…you’ll come back with a lot of horror stories. I will begin my stories with the quality messages I get on daily basis (sarcastically said).

online dating and bar scenes funny

Here are some examples of what NOT to say if you’re trying to get my attention in the first message.

This one confused me:

“Hey. If you are slightly interested let’s move fast to see if there is a connection K? I hope that does not sound to bad, I just thought of a sweet business Idea and have limmited time as of now. Thank you.” 

??I don’t get it, he has a limited time as of now? Is he in an infomercial? His offer is only good for a limited time? His next message should be: “Act now and be one of 50 to get a FREE cheese grater!”

funny infomercial dating

This is probably what this guy looks like in real life


Here is one from a fake account (very obviously because his picture was a computer-generated tall, dark, six-pack shirtless man):

“Your really pretty, you have a really pretty face! Im not just saying that as a pick up line
I really mean it! I was looking at other profiles, until I came upon yours, you made me stop and just stare at your picture! What is your phone number so we can see if there is chemistry between us and if it could lead to a beautiful relationship?”

And then provided an actual phone number…I am actually really curious to know what this phone number leads to. Drunk texting fun anyone? In all seriousness, though, this number probably belongs to the Craigslist killer. Too bad this was the sweetest message I’ve gotten so far…


Here’s one that is to the point:

“Hey ya, How ya doin’ ? I bet you have been hitting on daily basis by the members of this website. I was wondering with you are up for one night stand type of thing. Since i am not really looking for something too serious, i decided to give a shot with this website. Oh well i hope we can talk soon;)”

This guy I broke the rule of no contact for because I had bust his balls for this horrible message. I sent him a confusing, possibly I would be interested but it was too ambiguous to tell message. Especially for someone this dumb. He ended up chatting me at one point and we had a long conversation about how booty calls work. Not surprisingly, I was the one providing the education on this… Once I had become bored, I promptly told him I would never take a booty call from online and blocked him.

This one sounds like we are discussing a business deal. It would make sense because he is 48…

“Hi, how are you?
I would like to chat with you.
Can we meet for coffee sometime within next couple of weeks?”

I will tell him that I am booked for the next couple of weeks, but he could arrange something with my secretary possibly.

This one I don’t even know how to respond, so I didn’t…and of course he sent a second message:

“Hey beautiful, how are you? It’s so funny how the freezing morning makes you cuss at first with a toothbrush in your mouth at 6:30 a.m while it becomes your best friend with a warm sun up around noon time. Gotta love the SoCal winters, right? : )”

First of all, don’t start the message off with beautiful, it makes you sound like a douche. Second of all..WHAT THE EFF are you talking about??!!

Here is the “better attempt”:

“I’m sure work, friends, family, and all the other responsibilities must be keeping you busy. We’re living in a fast-paced crazy place called Los Angeles after all, right? Find your way for a quick minute and say hello sometime. It’ll be fun, I promise…I know the guy, he’s cool : )”

No, dumbass, I am not too busy to answer you, I just don’t want to. So please, don’t fool yourself.

online dating and grammar funny

Okay seriously, how is this even funny??

“So, what are the odds of a guy like you and a girl like me getting together?”

Don’t ever call me a dude. Period.

Here is an interesting approach if you’re an older gentleman:

“Any interest in slighter older, kind of interesting and adorable older man? 🙂
i hope you’ll reply.”

And no, this did not work. Because he was 55.

online dating older men funny

HappyEnding says: “nice photos”. Seriously, if you’re screen name starts with ‘happyending” don’t pass go, don’t collect $200, just go straight to the Korean massage shack down the road.

Here is an interesting way to engage a conversation:

“What do you like to talk about? Recently there were some tornadoes in the Midwest and South. Should people donate money to the American Red Cross? Or should FEMA take responsibility for aiding the survivors? Or should each individual pull themselves up by their own boot straps and fend for their lives? How much aid is appropriate?”

Seriously, I don’t even want to read the question. I am not in a Miss America pageant.

6 thoughts on “Stories from the online dating trenches

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