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Houston, we have a pussycat problem. A gay one.

After my last post I received a lot of interesting messages about online dating. In fact, some of you even sent me real life online dating messages from potential future ex-girlfriends. After reviewing some of the messages, I’ve concluded that we have a problem. A big problem. [Insert the obligatory lame Houston joke here]

When you message someone over a dating site you have to remember that this is their first impression of you. The girl you are messaging knows nothing about you, she has no idea how awesome you are. If your first message sucks, she probably won’t even look at your profile to see if you are a good match. I’ve included some real life examples below. Let’s take a look at where this went wrong and how we can fix it.

Example One (same person):

Sep 25, 2011 – 10:47pm
Hey! How are you? 🙂

Sep 25, 2011 – 10:49pm
Btw I’m a huge packers fan lol that’s what made me go omg I really have to message this girl lol my parents r from Wisconsin lol

Sep 25, 2011 – 11:16pm
Obviously I’m not pretty enough lol have a goodnight

This girl, let’s call her Mel, starts off okay but things go south pretty bad. First- initial contact should be more than just a “Hi.” The train of thought that was trying to get through in the second message should have gone into the first one. Minus all the lol’s. One “lol” is good, but if you have an “lol” every five words then that’s the equivalent of nervous laughter. Not too sexy right? Yeah I didn’t think so. The second problem is that Mel is way too sensitive and defensive. Look at the time stamps- she gives the girl she thinks is cute less than a half hour to respond before she accuses the other girl of thinking she’s not pretty enough.


U have 27 minutes to respond to me or I'll stab you...3,2,1

DRAMA alert. The “lol” does nothing to make Mel seem less butthurt over not being messaged back instantly. If you are butthurt that easily, you aren’t dating material. This is what Mel should have written:

Sep 25, 2011 – 10:47pm


When I saw your profile I needed to message you! We have a lot in common- I’m a huge Packers fan and my parents are from Wisconsin. Maybe we could talk about football and cheese sometime.

Have a great night!


This is how a grown-up says hello. Even if Mel NEEDS to insert an ‘lol’ into this message because it’s part of her personality and GOD HOW CAN YOU SEND A MESSAGE WITHOUT LAUGHTER? WHAT IS THE WORLD WITHOUT LAUGHTER- the message would still be effective. The key here is to get the other person to see that they could hold a conversation with you about things they care about. Fixed? Great. Now on, on, on to the next one:

Example Two (same person):

9/26/2011 8:07:04 PM
we need to go out… you are beautiful!! sorry so blunt, but shoot!

Sent Date: 9/26/2011 8:16:51 PM
hey you took my breath…can I have it back??? hahah so cheezy I know lol.. I have to be able to laugh at my self, I am just going to throw this out to you, I want to get to know you, maybe go for a drink or text for a bit.. (haha i suppose the TEXT should come first, then the drink) anyway let me know, i think you are real easy on my eyes, and I just started this fish finder… dont laugh at my dog and I, I think we might be starting to look alike… YIKES! Haha

Again, we have multiple messages without waiting for a reply. This girl, let’s call her Toni, did a few things right. She showed her personality. No, the person she is writing too might not like enjoy self-aware cheesy pick up lines, but the right girl will find it cute. Toni keeps it light in asking for a drink or a text and throws in some compliments. I would think Toni is a funny lady IF she used correct punctuation, capital letters and hadn’t sent the first message at all.

The first message is the equivalent to a catcall on the street. It doesn’t mean anything and girls that are used to being called beautiful by strangers aren’t going to respond. The second message is better, but again, let’s write like grown-ups when trying to get a date. Also, the last sentence is a little too self depreciating. It’s a little too early to let the girl you think is beautiful in on any self esteem issues.

bulldog Pictures, Images and Photos

Oh hai, do you think I'm a dog?


Example Three:

Hi I’m [name redacted] I’m new to all of this and I’m not sure how to start getting to know people so I would like to give u
my cell number so we can get to kno eachother. I would really like to get to know you. Plz feel free to contact me
at [cell phone digits redacted]

This girl is either in high school or a prostitute. Or both! Don’t send a message that looks like this and never include your number in a first message.

Example Four (same person):

9/10/2011 8:26:19 PM
Hey, how’s your evening

Sent Date: 9/16/2011 4:12:28 PM
Hey, how’s your day going?

Sent Date: 9/16/2011 6:17:56 PM
Do I just suck

I'm so shy. But if you say something sweet I'll be brave enough to leave my cup

I admit it, I have a soft spot in my heart for this person. Let’s call her Jac. Jac’s opening email wasn’t strong. Like I mentioned in Mel’s case, you need to tell the other person why she should talk to you. After double checking with the recipient of Jac’s message, Tami, she said she didn’t respond because she didn’t know what to tell a perfect stranger about her evening. If Jac really wanted Tami to talk to her (and the multiple messages indicate that she does) she needs to give her something to talk about. Online dating is hard and replying to someone who sent you a message can be just as daunting as actually reaching out to someone. So assume the object of your interest is shy and help her out.

Now the “Do I suck” message cracks me up and someone like me would probably respond to that. BUT again, Tami wouldn’t. If Jac really wanted to know why Tami wasn’t interested, she could have asked in a more serious way. Something along the lines of “I thought we could be a good match- is there any reason why you haven’t responded to me?”

Feedback from Tami could have helped Jac in the future. In this case, Tami didn’t like the message. But maybe Jac’s profile picture looks too blurry or old and needs to be updated. Or maybe Jac didn’t have enough interests and activities listed on her profile and didn’t give a sense of who she really is.

So there you have it ladies! Now get out there and message someone. Message her reeeaaaalll good!

Usually this is where I ask if you guys have questions for me. BUT I’m going to turn the tables. Do you all get these kinds of messages? Is it really that bad out there? Tell me about it in the comments, studmuffins.