The Playbook of the Toxic Flirt: How I Went Undercover & Witnessed the Horror of Online Flirting
So I, with an anonymous Reddit account, made a post a few months ago that became quite successful granting me the pleasure of being raised to /r/popular and /r/all — Reddit’s aggregation subreddits containing the most popular posts that day.
I shared a creative endeavour that I’d been practising, one that has been popularised by female creators in the past despite it being something that can interest anyone. Unfortunately, it seems that due to my choice to fully anonymise my profile and username, combined with the nature of what I posted, some users began to assume I was female.
I started to get comments referring to me as ‘she’, and then I started to get ‘Chat Requests’ from the few mistaken users who thought of me this way. They wanted to chat, flirt and, in some deeply unfortunate cases, sext.
To protect my anonymity, I allowed users to assume whatever they wanted in conversations both in the comments and in these instant messages. On one hand, I didn’t want to sell a lie to these users, but on the other, I’d heard about retaliation in the wake of rejection from so many women online, so I decided to keep it light and remain anonymous in conversations. I wanted my post to do well, and I didn’t want a disgruntled would-be sexting partner reporting it when he realised I’d lied about my identity.
So, for the first time in my life, I’ve been on the receiving end of the type of toxic flirting that I’d only previously heard stories about. I however, had a unique position, since my anonymity granted me the ability to have nothing material to lose, a position not often afforded to women online who have exposed their identities to the world.
As I deftly (and sometimes clumsily) tried to sidestep their persistent advances, here’s what I learned about problematic online ‘flirting’, distilled into a ‘playbook’ of techniques used by almost all of these chatters…
Play 1: Social Positioning
Scenario: You’re an artist without a historical portfolio of successes and you are not ‘known’ in the art industry, but your work is brilliant. Due to your fledgeling status, your potential and skill level aren’t common knowledge within the industry. An art gallery nevertheless opts to display your masterpiece, an exceptional piece of artwork. The only evidence that you can paint is currently getting rave reviews, compliments and success from within the industry itself and beyond. Regardless of any other mitigating factors about you, how would you suppose you would be treated by those who view your artwork? As an expert? As a peer? As inferior?
To answer this question appropriately, you’d need to know some information about the person you’re speaking with, because social positioning isn’t an absolute, it’s relative. You’re positioned socially above, alongside or below the person who you are interacting with at that very moment.
Usually, you may say that from those without your obvious talent, you’d expect to be treated as an expert; from those who are similarly talented, you’d expect to be treated as a peer; and from those who eclipse your own success, you’d expect to be treated as inferior. This, more often than not, is the way of the world…
Unless they think you’re a woman.
These three categories of relative social positionings, hereby named Expert, Peer and Inferior can be witnessed throughout these chat logs. However, unlike in real life, when treated a certain way by these chatters, there was no relative reference in order for me to judge their talent. What then was their reasoning for treating me as they did? What was their personal experience in the creative endeavour I posted about?
In some of the categories of interactions, the chatters were quick to demonstrate why they are positioning you into one of the three categories. You’d be surprised at how quickly this is established in a conversation even face-to-face. It’s human nature to know where in the pecking order you fall, and to give credit to those above you as a show of faith or humility. However, in the most problematic chats I had, they offered no evidence to support how they positioned me. Can you guess which category these chats fell into?
The third category of chatters, those who treated me as inferior, often started by offering ‘advice’, or ‘giving feedback’ in a condescending manner. This is the first time, I, as a man, had experienced mansplaining — offering advice or explanations without pausing to understand whether or not that advice is warranted, or even valid in the moment.
More often than not, this advice was laden with compliments, but it was still very clear to me by the form of their conversations and how they led them, that they thought of me as inferior. It felt like a very subtle form of that much reviled flirting technique known as ‘negging’ whereby the flirter attempts to insult the flirtee using backhanded compliments to dazzle or confuse them — it rarely leads to a successful interaction.
Perhaps this was by-design on their part, as a way to inflate their own self-worth, but it became a significant point of interest for me when those chatters’ profiles didn’t back up their egotistical social positioning. How then should I recieve advice from someone who has never engaged in the subject matter? If a tried-n-true expert had conversed with me in this manner, then it could be seen as a little rude, sure, but not unfounded because that expert has receipts to back up why they’re giving me this advice. In these chats however, it was both rude and unfounded, which is why I was able to notice it in-amongst the other chats I was having.
This is likely something that women have had to put up with from men since time immemorial, but it was the first time I was able to notice it happen to me. I tried to get them to justify their ‘advice’, simply by asking them if they too engage in this creative endeavour. At best they were evasive, but at worse, they lied — these were easy to spot due to their making wildly inflated claims about their talent or accolades.
Another method I noticed within these chats, that the chatters were using to artificially augment their social positioning within the conversation, was that they engaged in the conversation in a sort-of command position. In essence, they led the conversation, without respecting what I might want out of it, the topic changes when they want, they are the ones who get to ask questions, and they are the ones that like to be in control of the flow. Most of the time, this was subtle and was something I only noticed when I revisited the chats some weeks after to attempt to understand them.
Sometimes it would take the form of multiple messages in quick succession, without leaving room for consideration of my answers, other times, it would would take the form of sharp turns in flow, quick topic diversions and unrelated questions designed to control the conversation direction.
This, to me, was a strong indicator of a conversation that would turn toxic. It was the first thing I noticed when I looked back over them to determine what qualities these most heinous chats shared.
Play 2: Boundary Disrespect
I was determined to remain fully anonymous and not give anything away when talking with these chatters. Early and often, I gave my boundaries.
What is a boundary? It’s a line in the sand, it’s an unambiguous threshold, it’s a clear discussion of things you’re unwilling to disclose, or an act you’re unwilling to engage in. If you have that clarity and assertiveness about your boundary — whether it be a small boundary or a large one — then how would you feel if the person you’re speaking to attempts to break it, over and over again?
They would ask how old I was, or where I was from, and I would be clear that I’m prepared to chat with them, but only on the condition that I’m not required to give any information away. We can chat about the post I made, the creative endeavour as a whole, but no personal information will be shared. After all, my post was the veil they used to encourage me to chat in the first place. I endeavoured to keep them somewhat on-topic.
Below you’ll be able to read the techniques I encountered that the chatters used to attempt to get me to give this information away anyway, despite my clear boundary.
They would offer information about themselves — sometimes their full names, where they’re from, or their ages. It was clear, by the way they worded these information dumps, that they intended to use it to guilt me into sharing too. They willingly altered the dynamic of the conversation to cause me to be on the defensive, so that I feel as if I owe them something.
They would tell me that they can’t chat with someone they don’t know, and that I should give them ‘something’ at least, so that they can connect with me more deeply.
Sometimes they would conjure a wildly inaccurate persona for me, replete with a name they plucked out of thin air, and a detailed description of who I was. This was to bait me into correcting them. One insisted that I give him at least my name, so I provided him a ‘nameified’ version of my username for him to refer to me as, but he rejected it outright and determined that he would refer to me by the name he created from that point forward. A petty act of defiance against my draconian boundary ‘rules’.
The information they were asking for was often not material to who I was. But to me, it wasn’t the information I was protecting, it was the boundary. I had made it very clear from the beginning that I would not share information, and despite that, they then made it their mission to break that boundary.
If the chatters did this for some immaterial information about me, what would happen when faced with a more serious boundary further down the line? These men don’t have different rules for how they approach ‘small boundaries’ and ‘large boundaries’ — they instead have rules for how they get what they want, regardless of how their conversation partner feels about it.
I was able to use this to ‘test’ how open they’d be to a fuller conversation. Respecting a boundary, regardless of how insignificant the boundary is, is so important to any successful relationship — platonic, business or romantic.
One of the first things I’d be asked by these horny chatters was ‘Are you single?’ I’m not. I offered this information only because I didn’t want them to continue trying to flirt with me. Here’s how it almost always went:
Them: Are you single?
Me: No.
Them: I won’t tell if you won’t.
I didn’t apologise, and I didn’t attempt to downplay my unavailability; afterall, ‘no’ is a complete sentence. The frequency in which this ‘no’ was disregarded was alarming. I expected one or two chatters to sidestep it, but the sheer amount of contraventions where far higher than I was prepared for.
All in all, I think almost every chat attempted to break at least one, if not all boundaries I’d set, regardless of how confidently, or assertively I’d established said boundary.
We’re often taught that to get what you want, you need to be clear and assertive. This fact alone is often levelled at women who have to put up with these unwanted advances. I’ve heard stories from friends and colleagues about how they wanted to ‘break out’ of an unwanted chat, but were unable to — the standard response from men is usually something like “but were you clear about it, or were you trying to preserve his feelings?” I’m beginning to see, that for women, clarity and assertiveness matters little in these situations.
For these men, a boundary became a challenge. A locked door behind which lay a prize, and they would do whatever it took to access that prize, no matter who they hurt along the way.
Play 3: The Empathy Test
I toyed with the name for this play, it was between ‘The Empathy Test’ or ‘Being Wilfully Pathetic’ — and either works fine.
This is where the chatter will test you by putting themselves down, or identifying a flaw within themselves, with the hope that you’ll rush in and ‘save them’.
Sometimes it was deployed by people who elevated me to expert, putting me on a pedestal and bringing themselves down. Essentially, the chatters prostrated themselves in front of me, telling me how I need to teach them to be creative like that.
I caught myself assuaging their fears more than once, encouraging them, attempting to prop them up. It took me a little while to realise that they’re using me to boost their ego, I became a tool for them to repair their ailing self-worth. Once I’d built them up, they’d use the new found confidence to flirt with me within the same conversation — giving me, as a conversation partner, evidence of their ‘growth’ of character.
However, the initial lack of self-worth felt acted, false, like it was simply a technique for flirting that had yet to be named. It left me realising that I’d been tested. They wanted to force me to soothe them. This was not someone in a real crisis of confidence, this was someone who is using a crisis of confidence to manipulate me.
That’s the key here, it’s manipulation through and through. Nowhere was this more evident than in the most toxic variant of this empathy test behaviour, which was deployed by those who have been called out for their boundary breaking.
In some of these chats, the repeated attempt to break my most simple boundary left me feeling like I had no option but to call out their behaviour, let them know that despite their repeated attempts, I wasn’t going to fold, and the fact that they’d keep trying was poor form. Sometimes they’d back down and go back to ‘normal’ conversation, but sometimes they’d feign patheticness. Here’s an example that I’ve paraphrased:
Me: I’ve said that I wish to remain anonymous, stop asking me questions I’m uncomfortable with.
Them: I’m sorry, I’m terrible, I keep doing this, I’m sorry. I’m not great at conversations like this. I always do this, I always alienate people. I shouldn’t even be allowed to chat online to be honest.
The intention here is clear. They are attempting to ‘flip the script’. They want me to go from admonishing them, to supporting them. In-a-nutshell, this is a perfect example of how this manipulation works. They want to control the narrative. Their need to be in control trumps their need to ‘look good’ in my eyes; so they cower and become pathetic to bait me into picking them back up.
This play is all about manipulation, it’s purposefully creating an environment where they’re in control of the type of conversation we engage in. Once they start to realise that their other tactics are causing me to pull away, they will deploy this technique as a ‘Hail Mary’ to regain some favour. They are attempting to alter my perception of them. How can I possibly remain angry at someone who accepts their flaws and apologises?
If I won’t see them as a strong commander, then the next best option is to be seen as someone who needs saving, either way, they’re maintaining their closeness to me, and control over the conversation.
Unfortunately for them, I was able to see though it, and that made me even more angry than I was previously. They’d broken my boundaries and then attempted to manipulate me into forgiving them. These conversations felt fraught with conflict, I never felt comfortable, never felt valued or respected, I was just a plaything for them to kill a few hours.
Play 4: Overt Braggadocio
Do women ever believe men when they tell them how many girls they’ve brought to tears of ecstasy? How about how many times a girl has been made ‘wet’ in a guy’s very presence? Then how about when a man’s previous girlfriend keeps contacting him after they broke up because they were so good?
This play, to witness it as a man, was excruciating — it made my skin crawl. It was right there in the dictionary, right next to the word ‘cringe’. It was almost physically painful to open my messages to see a flurry of manufactured ‘testimonials’ from previous conquests.
This kind of braggadocio is never on-topic; it’s often shared unprompted and out of the blue. Sometimes it’s the first set of messages after I’ve agreed to chat. They are desperate to let me know how good they are in bed. Crucially, they do this before even asking my name, or working out whether or not I’m attractive, or ‘their type’, or even really a woman — this information isn’t important for what they’re trying to do. It’s important only for a real flirting conversation, but these conversations are anything but real flirting.
This is the ‘alpha’ behaviour in their eyes. Despite the numerous studies that disprove the idea of an ‘alpha’ in groups of animals, some men cannot separate themselves from this ‘alpha’ idea. It’s posturing. It’s the online toxic male equivalent of a peacock’s mating dance. They are showing me how good they are, they are showing me what they can do, and they are showing me how many ‘satisfied customers’ they’ve had throughout the years.
It’s disgusting, and I honestly can’t imagine a scenario where a woman sees all this, and a) believes them, and b) is willing to continue the conversation with the hope of ‘getting in on that action’.
So I spent time ruminating on why they do this. Why are they so willing to destroy any semblance of meaninful conversation before it even begins? I think I have an answer…
There’s a popular theory surrounding scam emails, you see they’re often replete with grammatical errors and spelling mistakes. The theory teaches us that this is by-design; after-all if you can look past the obvious issues with the email, then it stands to reason that you’ll be easy to scam. The grammatical errors and spelling mistakes are there to weed out users who are too technologically literate or equipped with enough smarts to accept a scam email, leaving just potential easy targets on their mailing list.
This sexual posturing feels like a test with the same purpose. It’s so obviously false and exaggerated that it’s going to weed out those that are too intelligent to manipulate. Those that are ‘turned off’ by such antics aren’t good targets for these men. They are whittling down the population of women to just the few who are pliable.
It’s the pliability of women that these braggarts value. They want to be in command, they want to lead, they want to know that they can break boundaries without drawing ire, and they want to be able to place themselves in any position and always have the woman respond with empathy.
If you find this type of posturing pathetic, congratulations, you’ve successfully ‘tested out’ of this braggart’s pool of potential mates. Great news for you, but not so great news for the next conversation this chatter has.
This is, I think, the same reason why some men start with a dreaded dick pic (thankfully Reddit blurs any images sent through chat, so I’ve been saved the fright of seeing a surprise cock). They’re not trying to impress you, they’re trying to see if you’ll respond. If you do respond, it means that you’re willing to look past their behaviour, and it means you’ve availed yourself to this man as a target for their manipulation.
In Summary
Reddit posts, by their very nature, are ephemeral, once the post disappears from the ‘front page’ its activity all but dies. All my chats happened within 48 hours of my viral post, and just look how much I was able to distill within that short time.
Women online likely have to deal with this in a significantly higher volume over a much more sustained period of time, and often when they’re younger and less experienced than I am.
This fact terrifies me.
I have two daughters who are going to grow up into this world and quite obviously be mistreated by men right from the beginning, and as a parent, there’s very little I can do about it without maintaining full control over their online presence, which is harmful to them in an of itself.
When these chats first started to unnerve me, I talked with my wife about how I should handle it; I considered just deleting my profile, since it was new anyway, I wasn’t tied to it.
Eventually we decided that this might be a way that I can teach my daughters about the dangers of chatting online since my anonymity gave me an armour against many of the risks faced by women all around the world. I wanted to know more about how women can be manipulated and tricked through no fault of their own, how subtle some of the techniques are and how quickly you can be shocked by how graphic these conversations became.
As I mentioned, none of this is the fault of women, they don’t invite this. In my case, the chatters have only assumed I’m female and know nothing further about me, yet it happened repeatedly in these chats. This flies in the face of all those who assume certain women, public figures or influencers somehow invite this behaviour. How have I invited it? The mere impression that I own a vagina is enough to send these men into a spiral of harmful manipulation and toxicity. If I have not invited it by my online presence, then why are we using the same argument when women face these dangers?
These techniques have been developed by men likely since before the invention of the internet in order to get what they want out of women. As a man, there are no ‘how to manipulate women’ classes to attend, which means much of this behaviour isn’t learned in any traditional sense — in my experience, it’s not spoken about between men either.
The terrifying part of this, is that this leaves two options for why this happens. Both are difficult to digest.
First, it’s that this behaviour is instinctual. That certain men have within them an in-built capacity to dominate a conversation to get what they want, and the techniques they use are unfortunately remarkably similar to one another. If this is the case, then it severly limits the options women have online beyond simply refusing to engage with people online.
The other option, is that this behaviour is cultural. The historic patriarchal nature of our society has placed men above women in almost every facet of life, and that we’re taught via societal osmosis, that we should maintain this status quo. This in-built patriarchal cultural pressure, makes me even more proud of the advancements the various feminist movements have made over the last 100 or so years to tilt this balance and alter the very foundations that society stands upon.
How then do we solve this? Do we just wait for new generations to grow up in a more equal society in order to stop this behaviour, or is there some way to fight back against it in a more meaninful manner?
Whatever the answer to this quandary is, one of the things that I need to do as a parent is educate my daughters. I want to be able to understand this implicitly, so that when my daughters inevitably face these techniques in the wild, they’re able to recognise them for what they are — not flirting, but manipulation.
Part of me wonders how successful a woman would be in a relationship if they eventually chose to meet up with a man that used these techniques. I have no evidence to support this, of course, but I strongly believe the manipulation and toxicity of these online chats would continue into face-to-face conversation.
Due to how quickly the popularity of my intial post rose and then fizzled, I’ve likely only scratched the surface of this playbook. There’s likely so much more out there to learn, so from now, I’ll be keeping a close eye on this topic. I want nothing more than to give my daughters the education they need to keep themselves safe online and in person.
