The Delicate Art of Dating Site Messaging, or Why Proofreading is Important, Kiddos!

Online dating came up in two different conversations I had today with two different friends. They both knew I had tried it in the past, and both knew my results had been pretty craptastic.

In actuality, my reason for pulling my own profile down a few months ago had little to do with craptastic results and lots to do with a horrible message I got from some random stranger on the site. It said,


I was stunned. I’d been on and off this particular site for over two years and hostility was not the norm. So I went to the guy’s profile. He was an unsmiling, ridiculously overweight, balding 50-something man posed shirtless on a boat. Because the ladies love a boat.

Obviously, I was being baited. He wanted a reaction. He wanted my attention. Knowing this, I decided to ignore him and not give him either. Then the Merlot kicked in and said, “Oh, yes, we will give him both of those things!”

So Merlot and I lit him up. Mostly Merlot. That bitch is crazy.

I don’t remember exactly what our reply said, but I know “that astrodome you call a forehead” and “go shave your back” were included somewhere in our rant. We might have suggested his trolling was some misdirected angst brought on by the shortage of Hostess Snack Cakes, of which he was clearly a fan. And I’m almost certain Merlot said he lacked the balls to call me a “ho” to my face and that I’d gladly meet him at the well-lit WalMart parking lot of his choosing to test the hypothesis…and kick his ass.

Feeling very pleased with ourselves, we hit the “send” button about the same time I glanced at the keyboard and noticed that the I and the O are right next to each other…and typing on phones is prolly hard with chubby fingers…and this poor schmuck probably just meant to say,


I felt terrible. Ish. (It was one word. If he can’t be troubled to make sure he gets it right, I can only work myself up to feeling sorta awful.)

Ladies, once you’ve launched your dating site profile, chances are good that you will be inundated with messages. The women outnumber the men big time on those sites, so when a new gal pops up it’s like some jackass only put one cinnamon roll on the buffet at The Sizzler. The men, they pounce.

Just remember this nugget o’ wisdom from Pulp Fiction – be cool, Honey Bunny.

And these other nuggets. They’ll help, too…

Nugget #1. Do not feel like you have to reply to every message you get. You will receive plenty that only say, “What’s up?” (he just looked at your pictures and didn’t read your profile). You will get many that go on for 18 paragraphs about everything you have in common (he’s needy – run away). You will be astounded at the blatant disregard for proper grammar and punctuation (these people do not need a mate, just let natural selection do its thing here, please).

It may go against every “polite” grain in your body to let the message go unanswered, but trust me on this – don’t answer. That first message is a door opener. Let those guys in and you (a) give them hope that they have a chance, and (b) allow your inbox to be flooded with more of their lame messages and novellas and assaults on the English language. You’ll burn out quickly, you’ll quit checking your mail, and then you’ll miss that clever message that makes you crack.

Nugget #2. When you do get that clever message, check out his profile before replying. I’ve received plenty of clever messages that came from guys whose profiles revealed big, BIG issues. Issues like:

The guy didn’t have a car/job/house;
The guy was only twenty-one (but that might be your thing, and that doesn’t make you a bad girl);
The guy was still “technically” married;
The guy once peed on his sister so his dad peed on him as punishment.

(You should spend some time perusing the singles in Kentucky. There is an inordinate amount of weirdness in that state. Like, peeing on your offspring is an accepted form of punishment there. You’re not gonna find shit like that on any Google search, my friends.)

Nugget #3. You got the clever message, and the profile checks out! Yay you! Now, it’s time to reply. Keep it simple – a few sentences, tops. Ask him a question in this first reply, so he knows you are interested in keeping the dialogue going. Don’t tell him your name yet. Save that for your second message.

And for the love of all things holy, proofread before you hit send.

Nugget #4. Once the messaging is going well, he should ask for your telephone number within a week or so. Feel free to give it to him if you’re sure he’s not batshit crazy. I can’t stress this enough. If any part of you feels like a red flag is waving in the distance, trust your gut and hold off on handing over the digits. Unless getting texts first thing in the morning requesting pictures of your feet is something you consider super awesome.

Nugget #5. Texting should give you each a good feel for the other, and if you’re clicking he shouldn’t wait too long to ask you out. And if you’re still sensing no red flags, then you should go! Don’t be alarmed if you never have an actual phone call prior to the date. I’ve found that most guys don’t call before the first date, and they end up being nice, normal guys. Be more alarmed if he never asks you out. There seems to be a large number of guys out there who want to text. Forever. Cut him lose if he hasn’t proposed a date within a few weeks.

Because dating is the point of all this. Getting out there. Meeting folks. Putting on your highest heels and looking fantastic.

I ended both conversations earlier today by saying that online dating can be a train wreck, but it can also be fun. Even the bad dates can be enjoyable, as long as “bad” doesn’t mean you had to call the cops. You just have to go in with the mindset that you’re going to have a good time. And you have to be smart about it, but we’ll talk about that in our next fabulous and exciting post…

Drop a Pin, Yo: Self Preservation + Online Dating = Winning


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