Texting Your Pants Off: An In-Depth Look at Sexting

I heard an interesting term on the radio today, “Generation Text”. The term refers to anyone born from 1990 – 1999, and is applied to describe the dependence on cell phones displayed by youths who grew up using them. This incarnation of the term was coined by Canadian politician, Ian Scott, when he attended a concert and noticed many audience members using cell phones, (talking, texting, or recording) he also noted that they all fit into the same age bracket (early to late teens).

Cell Phones at Concert

It's all well and good till you need a cigarette/ want to commit arson.

Hearing the term started me thinking, interaction in our society is becoming more and more text based, incidentally verbal communication is declining. We rely on text for far more than we used to, where we would make a phone call we now send a text message. The only time I make a phone call is when my texts aren’t being returned, my message is to complex to be conveyed in text format, or I need to communicate with my technologically inept father… also ordering pizza.

Text messaging has largely replaced several facets of modern life, but for the purpose of this piece, I have chosen to focus on one: seduction.

Dictionary.com defines “sexting” as: nothing, it’s a made up word.  However, Urbandictionary.com (today’s leading source in definitions for made up words/filthy sexual innuendo), defines sexting as:

“the act of text messaging someone in the hopes of having a sexual encounter with them later; initially casual, transitioning into highly suggestive and even sexually explicit.”

It’s just like our society to do this, weather we’re ordering a pizza or banking online, thanks to our digital resources we are evolving beyond doing any of the footwork in accomplishing the most basic tasks.

But how can we make them raise our children? Getty Images

There are reasons why sexting is becoming so mainstream, to the point of having a new word created to describe it, three of which we will examine today.

1. Proof Reading and Revision

When I was asked if I would like to write an article for Sophster-Toaster.com, my immediate thought was “what toaster dot what?” After a brief explanation and allot of procrastination I turned in an article about shoes, upon receipt the editor asked me if I’d ever heard of a spell check. The problem in this situation, a frequent one for me in fact, was that I got excited about the project (once I started actually working on it), cranked out a slapdash article and fired it off to the editor.

This problem can be mirrored by our social interaction, perhaps we meet some new people that a friend of ours “totally hasn’t seen in like forever.” They tell anecdotes you had to be there for (note: you weren’t) and tell jokes you don’t get (because, again, you weren’t there). It eventually dawns on us that we haven’t said a word in almost 10 minutes and we panic, we know every one is just wondering what’s wrong with that guy that Patrick brought to the party, seriously he’s just standing there looking frightened. Suddenly, unconsciously even, desperate just to be a part of the conversation, you open your mouth and the first thing that comes to mind tumbles out clumsily, for example, “I got lit on fire once!” this is commonly referred to as verbal diarrhea.

Miss South Carolina

You should see the picture I wanted to use.

After we say it we regret it, some days we regret it as we’re saying it but just can’t stop, that’s where texting comes in, just texting mind you, we’re not sexting yet, you just met these people. Now that we’re communicating via text we reduce the risk of blurting out random, awkward nonsense, for example, “Seriously, I was on fire for a whole 3 seconds”.

With the luxury of experiencing our conversation in the same way it will be perceived by the recipient, we have the opportunity to say “wow, that’s dumb,” which is exactly what the recipient would say, not a valuable sentiment in any successful seduction. Instead, we can rewrite the message, and rewrite it again until we have a desirable outcome, we can also avoid spelling and grammatical errors, but most people choose to just leave those in.

2. Face away from Face Interaction

Another advantage of communicating via text is that you don’t have to look at the person you’re talking to, for instance, I am 6’3″ and I hate talking to people who are taller than me because I have to look up for once, texting allows me to communicate with tall people. Similarly, some people have trouble talking to members of the opposite gender, (Not me!) texting removes a lot of this intimidation, it enables the shy boy to talk to a pretty girl without concerning himself with how pretty she is, furthermore, without standing next to her, she won’t have the opportunity to compare and conclude that she’s more attractive than I am, or he is, rather.

"She must have seen the neck beard, dammit! Every time!"

Awkward silences, stuttering, accidental staring, uncomfortable eye contact, not knowing what to do with your hands, these face to face faux pas’ are becoming a thing of the past, ushering in a new golden era in flirtation. Even if you have a stutter they won’t even know until it comes down to “Oh b-b-b-baby”, at which point, you’ve already accomplished your mission.

Nobody likes to strike out, another danger of flirting. Striking out refers to the moment when it becomes clear to both parties that no sex will be occurring between the two of them. This moment can occur suddenly due to one bad remark (see proof reading and revision) or slowly and painfully due to your insidiously off-putting personality (that’s this section). Sexting lessens this threat by removing the physical interaction, it still happens but it has been figuratively neutered. When you strike out you have failed your mission, but if you do it face to face, you’re still face to face; I hope you have an exit strategy or it’s going to get awkward. A text rejection, (retextion? yes) a retextion is less painful, you don’t have to look anybody in the eye as they shatter your self esteem, you don’t have to hang your head shamefully and march away from your conquest, and you can just forget about it, unless of course, you’ve sexted a good friend of yours – but more on that later.

3. Pressure’s Off:

When my dad was my age and wanted to do what people my age do, (have sex with each other) he would go to the local bar, “the ho-tel” as he likes to put it, he would drink beer and talk to girls (in person!) until one agreed to go home with him, and he assures me that they did indeed go home with him.

However, there are nights when none of the fish bite and you go home alone, maybe you made enough headway to secure a phone number from a fine potential mate, but even then this is before generation text was even conceived. When you make that call you still have to talk to people with your actual voice, the same voice that still cracks every time you pick up the phone even though you’ll be 21 years old, dammit!

Today, the process has been simplified, and the bar has been lowered considerably. The phone number is all you need to get, the seduction has yet to begin, now you can space it out instead of trying to cram all the romance (cramance? doesn’t work every time, sorry readers) into one evening. Granted, there are still some who prefer the one night approach and, in fact, are quite successful, but if you don’t have the muscles of a Greek god and the flexible morals of a 20 and 3/4 year old part time writer, you’d best not push your luck at the club.

The more practical tactic is to make a good first impression, obtain a phone number, and then edge your way in. You see, sexting is the escape clause for life’s greatest paradox: the better someone knows you, the less likely they are to sleep with you. Nobody wants to sleep with the real you, not that there’s anything wrong with you, for the purpose of this article “sleep with” refers to a one night stand; the foundation for any successful relationship is that they know and enjoy having sex with the real you but that’s not why we’re here. This is because after enough time you can no longer be viewed as a potential mate, you’re the guy who totally puked everywhere at The Salads concert last summer.

The other side of this sexy paradox coin is that most people don’t want to sleep with a stranger, the better they know you the better the chance of some nookie.

In summary, a sexual candidate will not sex you if they don’t know you well enough, nor will they sex you if they know you too well. There is however an equilibrium where they feel comfortable with you but not too comfortable, this is achieved best through the art of sexting.

Parabolas: finally pulling their weight.

The process of sexting works gradually, where pickups require speed and tenacity. If used properly, sexting is a low impact non-threatening approach. Starting with just touching base, the occasional “how was your day?” we then move on to more in-depth conversations, until the day comes when you make your move.

As we touched on earlier, the move can fail, resulting in the dreaded strike-out. At this point the seduction can be abandoned or salvaged, depending on your commitment level. Salvaging strategies include “that was just a joke”, “my friends took my phone”* or “sorry, I meant to send that to someone else”, the last one works particularly well in that its believable, text misfires happen frequently, spend 5 minutes on textsfromlastnight.com if you need some context, an added benefit is that this can foster jealousy and re-rail a failing seduction.

*Note: taking a friends phone and sexting random contacts can be great fun, particularly if you hate your friends


While sexting has its benefits over traditional flirtation, it also carries with it certain pitfalls, including but not limited to: picture messages, wrong numbers, misinterpretation, and The Friend Sext.

Sexting can include the sending of explicit picture messages, receiving these pictures is the holy grail of cell phone based seduction. Inversely, sending them is never a good idea as a certain congressman, whose name happens to be a synonym for penis, is currently finding out the hard way.

I feel this accurately sums up a complicated political situation.

This facet of sexting is common among couples as well, Cosmopolitan assures us that sending your man a sexy “pic” while he’s at work so he knows what’s waiting for him at home is a great way to spice up your relationship, and I’m sure they’re right. What they don’t tell you is that if that relationship ends those pictures turn from a thoughtful, sexy gesture to volatile ammunition: those pictures are going public. In fact, there are numerous websites making good money from cataloguing these pictures, nobody wants to be naked on the internet, especially not for free.

Wrong number sexting has the mitigating factor of being less harmful to your end goal, and more embarrassing than anything. I’m referring to when a sexually explicit text is sent to the wrong contact, at best it can be a friend of the same gender and the two of you may laugh about it later. Other consequences ranging from best to worst case scenario include, that same friend thinking you bare a homosexual attraction to them, sending to a friend of the opposite gender who then thinks the sext was intended for them, sending to a family member who is now privy to unwanted details of your sex life, sending to a family member who now thinks you bare an attraction to them or any combination of the above.

Another possible outcome, and exclusion to the less harmful clause, is when the sext in question is sent to a mutual friend of you and your current sexual candidate. If the intended recipient learns of your “attempted seduction” of their friend or associate, they will be less than excited when your sext reaches it’s intended destination.

Your sexts may also be misinterpreted by the recipient, sexting can be used to incite a casual sexual encounter, or more seldom, found a legitimate relationship. Whatever your intent, should it be perceived as the opposite, you will be subjected to many an uncomfortable situation.

If your intent is the standard “hook-up,” misinterpretation may not be an immediate problem; you may, in fact, successfully “tap that,” though problems will later arise. Hurt feelings and access to your phone number are not a favourable mix. You will likely be treated to a barrage of insults to your morals, your manhood, (or womanhood) your sexual prowess and anything else you may be proud of. Of course, if this is a frequent occurrence, there’s a chance you might deserve it, so there’s that.

Perhaps your intent is to foster a relationship through this less traditional tactic, it does happen, though studies have shown that neither gender predominantly views casual sex as a prelude to a long-term relationship and that they in fact engage in sex due to feelings of flattery or purely aesthetic attraction (read: alcohol).  However it happens, let’s assume you have now engaged in sex with one of your phone contacts with whom you intend to enter a relationship, the good news is you will now understand the gambit of emotions the former sexual partner’s texting insults to you have previously run, the bad news is, you’ll be experiencing them first hand. It will start with good natured day after texts, “how do you do?” and the like, when the texts are not returned, you eventually learn that you are being ignored and that your interaction with your recent sexual partner has reached its climax.

"Why won't you ring!? She told me she loved me!"

All in all, sexting is not an advisable dating tactic, a one night stand rarely leads to a relationship, less often when its initiated with a cell phone.

Probably the worst mistake you can make sexting, is The Friend Sext: a sexually explicit or propositional text to a close friend who you legitimately intend to seduce.

The Friend Sext can be embarrassing and damaging to a friendship, no one in their right mind intentionally makes The Friend Sext, most likely there is some alcohol in the mix. The best damage control is to deny up and down, the “friends snatched my phone” approach is the best for this situation as it absolves you of responsibility. It also doesn’t require an in-depth explanation as you share some of the same friends and you both know they’re jerks like that. Furthermore, the joke claim is less believable, and if you claim you were trying to sext someone else, they’re going to want to hear all the steamy, text based details.

The most important thing to remember is that your chances of having consequence free sex with a close friend are low, granted it does happen, there are even movies about it: Aston Kutcher and Natalie Portman’s No Strings Attached, or Mila Kunis and Justin Timberlake’s suspiciously similar upcoming Friends With Benefits, even then, these are Rom-Coms, and its safe to assume they fall in love in the end.

As I’ve previously iterated, to this friend you aren’t sexy, you are the guy who slipped in dog poo outside Wendy’s. Sexting may be the escape clause but, if you’re already friends, don’t put all your eggs in that basket, it’s probably not going to happen, and if it does, it won’t end like you’d hoped. Remember the graph?

As Generation Text enters maturity, it’s only natural that they should express their sexuality in a way that’s familiar to them. Sex has everything to do with comfort, and text messaging is a form of communication that teens and young adults are most comfortable with. It’s no surprise that sexting has taken grip of the young masses, nor is it an epidemic society need concern itself with. Sex is a part of life, and people are going to have it, sometimes young people, “sexting” is a popular bearer of the blame but that can be attributed to a lack of education on the matter, people are just afraid of what they don’t understand.  Instead of blowing the problem out of proportion, and arguing a point with words they don’t understand, these parents need to take a more carniferous approach.  Parents need to instead educate their children about sex; the good, the bad, and the ugly.

Granted, We have devoted our time today to learning how to manipulate someone into having emotionless, consequence free sex with you, however, I have detailed that there must exist an attraction between the two, which you can amplify by exposing them only to the positive aspects of your personality.  Bottom line: sexting is not magic, it is strategic, if somebody doesn’t want to have sex with you, they’re not going to, there are strategies to get around that, but they usually end in a life sentence, so let’s just forget about them. The point I’m making is that sexting is not the cause of teenage sex, a few text messages wont make a girl give it up before she’s ready*, you could write a damn book, and it wouldn’t affect the outcome.

With certain obvious exceptions.

*note: I’ve tried to remain objectively ambiguous thus far, I say girl in this instance for two reasons; firstly, I don’t recall anyone worrying about their son having sex too early, secondly, as a former teenage boy I don’t remember a time when I wasn’t thinking about sex, with the obvious exception of when I was thinking about the transformers, I was not picky, is what I’m saying.


Now that you know some facts about sexting, you can try your hand at it and win that special girl over, or apply your knowledge to know when he’s trying to dupe you. And yes, I’m comfortable making that generalization as the application of sexting largely divides along gender lines. Until next time: use a condom