How to Stop Sucking at Match.com or Other Dating Services… Part 2

As you may recall, I decided to become an expert at Match.com in my last post. Why? Because I can do what I wanna do! No, not really. I just figured a 2,000 word post would bore you all to shit.

Just to recap, my buddy, Chet, asked for some help with his online dating profile. He wasn't getting an snags on his fishing pole… Meant to sound dirty. In my first installment we covered his profile and tried to pare it down a bit and remove some of the “asshole” within. Today, we're going to talk about his approach in writing to women.

Carpet Bombing. Just a bad, bad idea.

Dear Chet was form messaging a lot of the hotties on Match. Slight changes to each message to make them seem “unique.” And sent them out he did, one after the other.

No responses.

That more than anything, I feel, is what made him want to reach out to me.

Carpet Bombing is only cool for blowing enemy shit up. Otherwise you're really carpet bombing your bridge to nowhere. Why would you do that?

You see, aside from having a totally “Punch You in the Asshole” bad ass name, Chet is a pretty cool fucking guy. He's funny and successful and giving. He's very social and can strike up a convo on just about any topic. Yeah, he's that fucking cool. I'd blow him. That should be enough, right? Wrong.

I don't know what it is with us men when we get on an online dating service. So many times we send these one sentence messages, with poor grammar, no effort, no personality and no hope of ever touching or seeing a vagina we didn't have to pay for first… It's as though our personality forgot to make the trip to the profile.

The Wrong Type of Message (aka Paying for a Hooker Tonight)

  • The following are three messages Chet sent out. Let me know how you think he did.

Hello fellow chef! Pleasure to meet you! I have always loved to cook and am just learning to bake now. My daughter brought up the idea recently and we have been baking ever since. We just made our first cake entirely from scratch. Icing and all! What's your specialty?

I have to say your picture caught my attention, you look beautiful. Let me know if you would like to chat, would be great to learn more about you.


Hello fellow movie buff! Pleasure to meet you. I have a degree in screenwriting and worked in the industry for a while until my career took a different path. I have been described as having a head full of random pop culture references. Have you seen Moonrise Kingdom? It's amazing. What's your favorite Wes Anderson movie?

Anyway, I knew that anyone who is a fan of British humor HAS to be great. Feel free to check out my profile and let me know if you'd like to chat a bit more.


Straight hair and small nose? Are you sure you are Jewish?!? I was raised Jewish myself and don't fully practice anymore, but I can still recite the four questions on command. I noticed from your profile that we have quite a few things in common. Like you, I love to dance. (I am guessing that is the thing you do often to release stress.) Where do you like to go dancing?

Feel free to check out my profile and let me know if you'd like to chat a bit more.


PS – Call me a metrosexual, but I also like pedicures. And last time I went, I wasn't the only guy in there!

A few things to note here:

  • Never ask a woman to call you a metrosexual unless she's repulsive and you don't want to kiss her.
  • Chet is a personable guy  and can talk to anybody. He would never walk up to someone in real life and say “How ya doin' fellow poker player!” So why do it online? Who the fuck does that? I still have a penis and a shred of self respect. I wouldn't even do that.
  • Sure, it's nice to compliment a woman online, but I wouldn't open up with that right out the gate. To me, it's like saying: “Oh, hi there, my name is Chet, and crazy, but THIS IS MY PENIS!!!! RAAAAAR! LET IT RAIN BITCHES!!!!!
    Again, don't be that guy.

How I do messages

Since I'm a self-labeled expert, I know a thing or two about this shit, okay? So the following are messages I sent to women.

My rappin' skillz aren't what they used to be and I have to be honest, I did plagiarize the rap below because all I had was “chill with Benadryl, bitch!” So there's that…

Straight out of Mordor for more
Wizards come to your door
Don't step to us
‘Cause we the number one sorcerers
Pour more of that maiden bangin' potion
Pop the dragon into three-legged motion
Now we coastin'

So, the above rap will either make or break me because if you look it up you'll either roll your eyes, or give me a cyber hi-five.

I seriously dig the profile, you seem like a lot of fun while also being maintaining a level of pretty that defies your ability to kicketh the ass.

Shoot me a message, if you're interested shorty (I'm taller so I can say things like that)

-This guy

This next message, the lady replied with “I'm work at 4pm today, let's chat. Here's my number +++++++++ we can text, too, but not a fan of texting.”

Hypothetically speaking, if I told you that “you have a nice butt” as evidenced in your rock climbing photo, would you hold it against me? Okay, I know your natural reaction is probably to be appalled, just know that I was trying to be funny… I often fail at that.

Anyway, I liked your climbing photo and not just because of the butt shot, but I'm sure that If I was in danger of falling off a mountain that you might be able to help my hopeless and hapless self. =)

If you'd like to chat some time great, or if you feel like cussing me out because I was rude, that's fine too. Good looking women physically or verbally abusing a guy are hot… Yeah, I just said that.


And lastly…

So, here you are being all tall with tattoos and scar for the OkC world to see. I like! =)

I dug your profile and figured I'd shoot over a message and tell you how cool I am… I mean, my mom says I'm practically cooler than the other side of the pillow, so you know that has to count for something… Right? No? Hmm, you're a tough clam, aren't you?

In any case, if you'd like to chat, shoot me a message some time and tell me about that spinal surgery you had. I'm guessing you were kicking too much ass and had to go under the knife from the physical stress of it all. Am I right, or do you need to set me straight?

At the time those messages had been sent, they were the only ones I sent, each one yielded a response and I went out with two of the three women. The difference between my messages and Chet's is that my messages are me. That's how I would talk to some random woman. Anyone who knows me could attest to that.

Final Thoughts

  • Be natural – No one likes an asshole; people like assholes who try too hard even less. Cut it the fuck out and be yourself, even if yourself sucks.
  • Imagine you're talking to these people in person. What would you say if they were standing right next to you? Would you pull out your penis pics for her to judge?
  • Don't over do it. Be fun and funny; stay within yourself and flirt.
Author Profile

Alex is the founder and managing editor at the Urban Dater. Alex also runs: DigiSavvy, for which he is the co-founder and Principal. Alex has a lot on his mind. Will he ever get it right? If he does, he'll be sure to write.

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  1. You definitely bring up some good points. It’s just that it is so hard to type something the way you would say it (if that makes any sense at all). I guess it’s from having to write so many papers or something, but every time I try to strike up a conversation online I do the same thing as Chet. And my name is Lance, so I don’t get the whole cool name point. I think it’s too easy to put a lot of thought into what you are typing and then edit and re-type. Maybe I should just try typing with the screen off or something. What do you think?

  2. yikes, how old were these women ? I thought you had to be at least 21 to get on dating sites?

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