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Sending the First Message, or, How to Meet a Pen Pal

Dating a pen pal 🙁

Your profile is shiny and polished.  Good photos and great descriptions!  It’s kept updated.  You are faithfully following the greatest adult dating blog in the world, here at, taking careful notes. You’re ready!

Now you may have found a good match. Try to save that good match you found, so you can light post-coital cigarettes later. Because we’re going to tell you what to say, and what not to say. How to hook up. To make sure you and your potential match don’t let a good thing get lost in the wrong words and end up becoming pen pals for life.


You don’t always have to wear hoops and jump through bells and whistles, unless you’re into that sort of thing.  You’ll be surprised how effective a simple introduction can be:

“Hi, I’m Margaret.”

Except you would use your own first name.  Especially if it’s Margaret.  In many cases, first names will already be on profiles, but in making a formal communicative introduction, it’s not redundant to restate it. It will also help you to remember their name if you fall into the sheets passionately, more than a pen pal would.

Something very direct and specific can be added to something simple to come up with a winner first message like this one:

“Greetings. Your profile caught my eye. I think we may have a lot in common. Would you like to meet for a drink tomorrow and see if we hit it off?”

Notice the greeting there. It isn’t What’s Up, or Sup, or any of their derivatives. The market’s flooded with them. Distinguish your message. Avoid also Hey, Hi, and Yo. Try these:


Everyone loves “Charlotte’s Web,” even adults. What’s not to love.


(Exclamation point optional.)

“Ola, Bonjour, Buongiorno, Ciao!”

You’ll want to do a little research, to make sure foreign-language greetings are likely to be understood. They should: these in particular are a pretty common part of the western lexicon. But if your match’s profile says they were born in Puerto Rico, or Montreal, for example, all the better. Which leads us to:

Do and Use Research

Ask a question about their profile. Take a look through. Ask them where they are in a particular photograph, or what they’re doing. If you think you recognize a spot where they’re being photographed, say

“Is that downtown Detroit? I love downtown Detroit. Go Blackhawks!”

Or something like that. You can also find in their profile something about them to compliment. But avoid most physical characteristics. Because we know you: you’re going to use the word Pretty. And saying “pretty” makes just about all of us sound like tremble-lipped tenth-graders who still blush over exposed brassieres in the Sears catalog. Instead, compliment a garment choice, a hairstyle, a visible tattoo.

“The orange of that jumpsuit is a great color on you. When are you eligible for parole?”


“I have the same dress; I LOVE it.”


“The navy coveralls look great on you; how long have you been a sanitation worker?”

You can also find something in their profile that you can relate to:

“I see you’re baking in your third picture. I love to bake, as well. Did you go to school for it?”

Chat started, common ground achieved, an exploration of specific common interests initiated, and your close attention clearly indicated. Get a room. Or at least a chat room.

Common Interests

It’s tricky, because there are some very broad questions that people are bored with answering. Like “what do you like to do?” But there are some sweet spots where you’ll find things that people love to talk about. Asking about music has become such a relevant and ubiquitous part of getting to know both platonic and romantic connections that it’s almost a relationship milestone now. But we think it can come early in a conversation, especially if music is referred to in their profile.

“Salutations, Devin! I noticed in your profile that you love going out to see live music. I do, too. What kind of music do you like?”

If you both have a good amount of interests on your profiles, but none that converge enough to start a chat, you can try this fun, rapid-fire either/or word game that works as well in messages as it does in person.

“Good evening, Margaret! Which do you like better, purple or orange?”

From the first answer, move on: Unicorns or Dragons; Blue or Red; Hot Dogs or Hamburgers; Coffee or Tea; Baseball or Football; Cancer or Florida; Pie or Cake; Zoo or Aquarium; Wine or Beer…? The goal is to have fun getting your potential match talking about themselves, and everybody loves that, unless they’ve recently been subpoena’d by a grand jury. And you will eventually find a number of common interests and preferences to bond over. (If you have kids in your life, a modified version of this game is a blast with them, too.)

General Tips

Use Proper Language

We can’t reinforce this one enough: you don’t really know who you’re talking to, so use language as well as you possibly can. Can the netspeak. Speak in full sentences. Skip the single-letter words, except for I and A. He or she might be a maths major for all you know, and if you say

“I got a ? 4 u ?”

They are just as likely to try to solve for U as they are to respond to you. Don’t be lazy: show them that they are worth the herculean effort involved in actually typing out two or three extra characters. Sure, you’ll be tired after, but really the keyboard does most of the work. See how much better this looks:

“I have a question for you…”

Note the use of ellipsis (…). This is an effective way of achieving the result of a question mark in a sentence where it would be grammatically incorrect. It lets your potential match know that their response is assumed and that the rest of your statement is forthcoming. It’s a little thing to use to make yourself appear better at written communication than maybe you are…

Try to Catch Them When They’re Online

If you do this, you retain control of the conversation. Otherwise, you might get an alert that they’ve responded and are ready to chat when you’re in the shower, or the crawlspace, or taking your father to the urologist, or sleeping off a hangover at ten in the morning. You won’t be at your best. If they’re online, they’re most likely ready to chat for a bit.

Be Humorous

But be good at it. If you’re not, we don’t know what to tell you. Look up some jokes online. Go to comedy open mics and try to fine-tune fifteen solid minutes of material. No, don’t do that: those open mics are bad enough. Be quick. The advantage to chatting online or via text is that the other person doesn’t really know when you’ve seen their message or how much time you took to respond. So if they say

“How are you?”

You can spend the rest of the day and the next day, too, coming up with the cleverest, funniest response that you are capable of:

“Well, I’ve never had myself, but I’ve heard I’m pretty good. Sorry so long: was taking my dad to the urologist. How are you???”

Not everyone is going to be good at humor. But if it’s an asset of yours, use the shit out of it.

What Not To Do

Don’t Use These Words: Hot, Cool, Sexy, Attractive.

Hot, and Sexy make you sound like the Bro-Prince of Bro-Dom, bro. Cool doesn’t mean anything at all. And whenever we hear someone use the word Attractive in this context, it always kind of sounds like they just learned the word a few minutes ago. As a rule, stick with words you’ve known awhile. Except Hot, Cool, and Sexy.

When you send that first message introducing yourself, do not repeat information that is on your profile. If your match couldn’t read when they checked out your profile, they probably still can’t. Instead, try saying the same things, but in ALL CAPS; maybe they just have hearing issues. And if they didn’t bother with the text part of your profile, it might be because the photos were all they needed, so just ride along.

Don’t Ask Redundant Questions.

If you’re about to chat with someone on an adult dating site like, you should have a pretty good idea of what they’re looking for. When you ask

“So, what are you looking for?”

What you’re really saying is:

“Hi, I’m a little insecure that you would sleep with me anytime soon, so can you just reinforce that you have a profile on because you want to hook up?”

Insecurity so sexy.

There are a lot of things you could ask that are very likely covered by their profile. Take a quick look first. You’ll probably find where they’re from, what they do, and their general dimensions, which you probably shouldn’t ask, anyway.

HookUP Tonight.

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