How to be a Chatbug®: General Advice for Dating Online

chat-room-3To Blinky,

I recently met a young lady at a party and we really hit it off. We talked for nearly two hours about a variety of subjects—- our favourite tv shows, the last baseball season, and we really bonded over the way that certain smells can remind you of a certain memory (tapioca always reminds me of a summer I spent working at car repair shop).

So things seemed to go really well with this girl, and we even promised each other that we would keep in touch. I asked her for her phone number and she burst out laughing and said, “You use those things?” I looked like such a fool, I could have killed myself right there. She then informed me that if I wanted to contact her I should “chat” with her online.

I signed up for a “chat” account with Microsoft and added her right away. We have “chatted” a few times online, but none of it has compared to that in-person conversation we first had at that party. How can I recapture the magic of our real-life conversation online? What do I do!?

Thanks a lot,
Hoping to be a chatbug

Dear Hopping,

While I would like to help you, your statement has sent my mind running off on so many tangents and in so many different directions, I feel that any chance of a cohesive answer on my part is quickly “Hopping away”.

Where can I even start with you? To be blunt: there is no chance that you will ever be able to foster a relationship of any kind with the woman in question.
Your first (and most enormous) mistake was talking to this girl face to face, a practice considered so barbaric and archaic by our modern times that you might as well have slugged her with a mammoth leg, slung her around your shoulder and dragged her off into a cave to rape her over a newly-discovered fire. Furthermore, your asking after a “phone number” is as confusing as it is anachronistic: you are neanderthal wielding an astrolabe. Mentioning phones is like exiting an expressway to a sexual suburb — its a turn off.

For our hyper-modern times, there is only one mode of communication: Chat. All other mediums are outmoded, outdated, and offensive. Think teen hearthrob Jonathon Taylor Thomas asks for phone numbers? Think he talks to girls to their face? Wrong. He chats. How do I know? I am chatting with him right now (and he says: “SUP HOPPY”)
Here is why it is impossible for you to “recapture the magic of your real-life conversation” online: Magic doesn’t exist. It’s hogwash, poppycock, hokum horsefeathers. What you thought you experienced as  “magic of real-life conversation” was just the chemical reaction of explosions in your brain because both of you were inevitably riddled with insurmountable personal anxieties and a crippling fear of a lifetime of loneliness.
Chatwise, the only advice I can give you is: Add her, block her, meet someone else online, and move forward.


The Chat Maven

The Right Honourable Blinky,

I feel I must introduce myself to you properly. My name is Reginald Vel Johnson the 3rd. I am what many refer to as a “lady’s man.” I have no difficulty meeting and bedding women of all shapes, sizes, colours, ages, shapes, kingdoms and creeds. Recently I have begun worrying that the interest I receive from ladies may be due to a) my incredible good looks, or b) my royal lineage.

A jester in my court told me about this new “chat” phenomenon. Normally I would not pay attention to the words of such a commoner, but this is an ambitious young jester and I do not believe he would steer me wrong, for fear of demotion or beheading. He told me that online chatting is one way to tell if a woman is truly interested in you. In the online world, all we have is words, correct?

How do I acquaint myself with the chat world? How do I meet women in this universe? Do you have any chat numbers of women that I can type at?

Much appreciated.

Yours in perpetuity,

The Kingdom of Tsultu

Cherished Regibald,

I offer a sincere welcome to the world of chat-dating. While this might appear a distant, futuristic, alien and hostile land to a man of your caliber and time period, there is no need to feel threatened or overwhelmed. There are a few simple steps that even the newest of beginners can follow to ensure that the girls you woo are quickly bitten by your chatbug.

First, a note on history: Chat-dating has its precedents in the Victorian Period, with the culture of letters. Men would court women from a distance, using only the power of their words to the point where the pen became the sword, all as a device used to mask their homosexuality or undersized genitalia. This was the behavioural norm for men and women until 1911, when the world ran out of envelopes and quills.

It is certain that have already heard the common expression for spending leisure time browsing sites on the internet, “weaving the web”. Men often weave the web when looking for world news, statistics about sports, videos of women demeaning themselves, and jokes about golf. This popular and useful expression can also be extended as a metaphor for your talking to girls online. Using chat, a man will carefully weave a web of deceit in which he catch women (the “chatbugs”). It is for this reason that men are most commonly referred to as “webmasters” and “metacrawlers”. As an exercise, try spinning a trap of instant messages from which it would be impossible for a woman to escape.

Sounds simple enough, you might tell yourself. But how does one “weave the web”?
Nowadays, men use phrases (“What is your ass size?”), acronyms (TIAAAS -That Is An Acceptable Ass Size”), symbols (8===> –glasses, a very long nose and a smiling mouth, to indicate that the other is lying about their ass size, but that ultimately you find this amusing and not angersome) and “Links”  (generally to the website with the largest collection of ass and ass-related images). Next time you are weaving the web, scouring for links to send to your fishing partner or workbuddy, keep an eye out for links to send to chatbugs.  If no chatbugs are online, earmark the links and save them for later.

Finally, I would like to congratulate you for taking this step, and welcome you to the future of dating. May the bells of victorious chat forever chime in the Toottie Kingdom.


These last couple days I’ve been chatting with this girl, and its been going pretty smoothly so far. I was even thinking of asking her if she wanted to chat with my parents. But now I’m starting to suspect that she has a boyfriend. We will be chatting and every so often she will let something slip like “Hold on, I have to text my boyfriend” or “Did I mention that I have a boyfriend?” What should I do? I am very lonely. Do you think  I should tell her how lonely I am in the hopes that she will feel bad for me and break up with her boyfriend out of pity?


Seeking advice.

Always be in control. Girls like to know that they are not the only bird in your gun’s target. If a girl says “I have a boyfriend”, come back with “No problem, I have five girlfriends.” Never let anyone know how lonely you are. One of the most common questions for a girl to ask when chatting online is “When was the last time you had sex?” Don’t be afraid to stretch the truth.  Is kissing sex? Is masturbation sex? In a way, yes: masturbation is a sexual act. So when, online, a girl asks you: When was the last time you had sex? The answer is always “I am having sex right now”.

Yours for now,
Blinky the chatstar

Bear Dinky,

First of all, a big thanks from Whitby Ontario for all of your great advice concerning the realm of chattery. Your selfless act is truly appreciated.

I come to you with a slightly embarrassing question. I suffer from what is know as CD, or, “chat dysfunction.” I am a pretty good chatter, and girls like to chat with me, but it seems like whenever our chats are moving forward into a slightly flirtatious or romantic territory, I always ejaculate my chats prematurely. I’ll look up at the chatbox and see that I’ve sent 40 messages while the chat-lady in question has only sent 2. I usually have no memory of any of these chats sent and often many of them are vulgar and shameful. I have ruined many chat relationships because of this problem. Even when they are not shameful or vulgar, I have ruined the chat like a fat child would ruin a day on the see-saw. I believe the girls feel overwhelmed and perhaps like I am spending too much time paying attention to them, like a fat child who pays attention only to his food and not to his friends who want to have a fun day on the see-saw.

What can I do? How can I force the moment to its good result without forcing the moment to its crisis?

Thanks a lot,


A lot of guys e-mail me, with the similar questions about how much chat is appropriate for one girl, wondering what the proper you-them ratio should be, and worrying that they are disrupting the sexual flow by bombarding girls with constant messages. I’ll tell you what I’ve told everyone else: Premature E-chatulation is an overdiagnosed problem. Men are supposed to take the chatbull by the horns, this is a fact of scientific biology. Men who worry about not giving women the appropriate response time are spindly fairy children who should start questioning their sexuality.

It is important to remember the Golden Rule of internet seduction: A.B.C. (Always be chatting). ALWAYS be chatting. Chat at all times–while at work, while at home, while working from home, while eating dinner. Use your iPhone to chat during transit. It is the simplest rule and one that people often forget. There is no instant way to become a chat Casanova, one can only improve ones muster by constantly shaping the craft. (Helpful tip: Maximize your time by having 5-10 chat windows open at once. This will greatly improve your abilities while also delaying your response time within individual chats, should that matter still concern you.)

One important thing to do is distinguish between genuine chat and idle prattle. Girls can immediately tell the difference, they smell it instinctively. If, online, you are prattling away like an elderly man waiting at a bus stop to die, you will likely scare away girls like an elderly man might scare away his grandchildren. If, however, you are chatting out hit after solid gold hit, then the silence on their parts means something else entirely. It means you’ve won the chat. Girls love winners.
So have confidence. If your chat is good and your game is on, then 40 consecutive chat messages followed by complete silence is a best case scenario.

Always Blinking,


What is the percentage of internet chats that blossom into physical relationships?


To be honest, an exact percentage is hard to determine, but the number is almost negligible. I haven’t yet had any internet chat relationships become real relationships, and when you start plugging “zeros” into calculators the numbers get all wumbly. I suppose to adequately answer your question I would have to get someone who is better at math.

Calling out from Chatman’s World,


Have any questions about the Internet that you would like Frank ‘n Beanz to answer? Send all questions, comments, queries and spam to We will answer every e-mail.


One response to “How to be a Chatbug®: General Advice for Dating Online

  1. dear blinky,

    sometimes if i have been chatting for a long time and i haven’t gotten out of bed all day (except to pee) i start to feel kind of nauseous, like i have been eating too much ice cream – does this happen when people meet in real life?

    hope you can help!

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