Conversational Skills Guide

A lot of guys struggle with generating interesting conversations, replies to conversations, and things to say in general. This guide is a wide-ranging toolbox of conversational techniques

Guide is intended for guys that could really use a deep-dive explanation of what good conversations contain

As a reformed and literal autist, I wish I would have had this when I was younger and unable to converse

What is Good Conversation?

What is a good listener, speaker and conversation?

The Average Listener

People enjoy good conversation often for conversation and entertainment value alone.

A lot of great conversations have no objective to be achieved apart from being an enjoyable social interaction. People enjoy socializing for the dopamine, serotonin, and oxytocin hit alone (outside of convo leading to logistics, info sharing)

Good Conversationalists

Most "good" conversationalists provide emotionally rewarding ebb and flow of literary devices outside of mundane and literal conveyance of information

If you watch the guys getting the most pussy and the life of the party, most are NOT communicating literal information or even meaningful conversation for the most part. They are sticking to FUN and stimulating conversation

If you are sticking to straight up literal commentary you will bore your audience unless the information itself is inherently interesting which is not something you'll frequently have (i.e. highly interesting factoids etc.)

Great Conversation

"Great" conversation employs a lot of rapid idea generation as well as literary devices and other conversational techniques that often lend to humor, wit, or banter

Topic Generation:

  • Observation
  • Association
  • Existing thoughts (random)

Literary Devices:

  • Exaggeration/hyperbole
  • Vocab-swapping (synonyms)
  • Euphemisms
  • Simile
  • Metaphor
  • Analogies


  • Impromptu/framing
  • Roleplay
  • Banter


  • Reactions/Continuity
  • Storytelling
  • Asking listener(s) good questions


I've seen guys on here ask "what is funny?"

People often find things funny that are true but aren't commonly spoken, comparisons that are accurate but that most people didn't previously consider, unexpected twists, random bold statements that come out of nowhere, quirky twists on information, silly behavior or recollections of it, jokes that make them think, etc.

Most lighthearted statements that pull people out of their normal train of thought and make them have to slightly think and connect dots rapidly (especially if it's related to things a bit outside of normal socially acceptable behavior) tend to get laughs

Topic Generation


Observation is the most available but often least reliable, but easiest to start out, thing to generate conversation unless done sparingly and intentfully

Environmental Observations:

Simply commenting on something in the environment. Renders you solely dependent on the interest potential of the environment, thus it is not terribly reliable

Best used to people watch, point out observations of notable curiousity, or other things that could lead into additional conversation topics

Listener Observations:

Pointing out something you can visibly see on the listener has more potential but is more polarizing. Asking them about something, making an educated assumption, etc. The deeper (and less shallow you go) the more potential to have the listener saying "that's accurate/ not completely right, what made you guess that?" etc.

It gets you talking about what people love most, themselves.

And if done right, can lead to rich conversational content, teases, etc. that form a favorable impression of you.

Free Association

Free association is an indispensbable and powerful technique that is essentially necessary for all of the litery devices and most witty and fun conversation

Free association is essentially taking a word (any word) and thinking about things related to that word

For example: "Wet"

  • Water
  • Rain
  • Drinks/Thirst
  • Ocean
  • Beach
  • Water Park
  • Sharks
  • Pirates
  • Vaginas/Arousal

One singular word has a lot of different associations that can easily come to mind depending on where you want to take a convo. Which is important in game and escalation because so many euphemisms for sexual words can be arrived at through association

Association can be easily practiced. Pick any word and come up with 5 related words. From one of those words come up with 5 more. So on and so on. As you'll see you'll end up on a wildly different topic. Can be practiced till you can take any word and arrive at your desired conversational outcome

Pre-Conceived/Random Thoughts

Existing thoughts are a valid dead space filler. If no one has anything to say you can bring up something randomly on your mind or something you'd been thinking about that day already

(Not always reliable if you're not used to generating interesting things to say yet)

Common reactions to the random thoughts are usually "that was random haha" "how did we go from x to y in this conversation?", etc. But that's fine if it's a good topic if you can turn the sudden transition into a tease or banter or successfully transition to that new topic

Another common reaction to such a change is usually that the new topic will quickly morph into another new topic, which is fine, you kept a conversation from dying and saved everyone from awkward silence and freed everyone else to say random shit on their mind

Some common ways to introduce this is:

  • hey did you hear about [current event/celeb/ meme]?
  • oh, by the way I was thinking...
  • you know earlier today I started thinking...
  • this is random AS FUCK, but xyz
  • that reminds me (even there's no way the last convo should remind you of that)

It doesn't really matter how as long as you're confident about it. It usually gets a good laugh from the transition alone

This is not meant to be an all-inclusive list of ways to generate topics but it covers a lot of them

Literary Devices

Conversation Enhancers


Boring conversationalists describe things with overly accurate descriptors, sometimes even taking the time to think of the exact amount of something, etc. or backtracking and interrupting the flow of what they are saying to clarify

"I was having this conversation and I had to answer [thinks about it] 6, and I had to, well actually it was 7, questions... Blah blah details blah blah"

Bleh. Boring convo. Disengages the listener who doesn't need to be literal in casual convo.


"I was having this absolutely mind-numbing conversation where I got asked like 100 questions"

Is a lot more exciting

"Bro my ex banged like 10 dudes the week after our break up"

When she fucked 3 guys within a month of the breakup, is actually a double exaggeration (both in exaggerating the degree upwards and time period to sound more frequent than it really was)

Vocab-Swapping (synonyms)

If you don't already have a great vocabulary of tantalizing synonyms and slang substitutes, save them as you see them in a notepad or something

One of my favorite conversation enhancers is simply swapping out boring and literal/accurate words with more stimulating versions of the same word, even if it's slightly overkill or innacurate (which makes it funny). This is sometimes exaggeration and some times just a more engaging synonym or slang version


Base word (normal typeface), better synonym (bold), slang version (if one, italics)

  • Weird/taboo, degenerate, salacious, kinky, cringe
  • Bad, atrocious, god-awful, dingey, worst-conceiveable, common-loot, trash
  • fun, exhilarating, tantalizing
  • Good, excellent, fantastic, kick-ass, dope, [word]-gasmic
  • Normie/boring, mundane, basic, pleb
  • Expensive, exorbitant, lavish, Gucci, high-way robbery
  • steal, extort, finesse, casually acquire
  • Mean, sociopath, vicious, villain, savage

One of my favorite methods of acquiring new and relevant word choice is to look at meme pages and adopt the words people use on extremely funny memes, which is also good for casually learning current events with low effort

Word-Enhancers (adjectives)

Adding additional words before a word swap, especially words with a lot of emotion, bias, or intensity, will give additional boost to your language

Words like:

"Straight-up, downright, absolute, pure, etc."


"Downright savage" , "pure cringe", "absolute clusterfuck"

Combining Both Skills

As you can see a lot of these swaps and enhancers can easily make an otherwise boring and even short one-liner hilarious and highly engaging

Girl: he did x so I didn't text him back after the date

Boring: that wasn't right

Fun: you're a straight-up villain, Abby

Euphemisms/Double Entendres


Euphemisms are: a mild or indirect word or expression substituted for one considered to be too harsh or blunt when referring to something unpleasant or embarrassing. "downsizing” as a euphemism for "cuts" or "left us" as a euphemism for "died"

Euphemisms can, however, be pretty funny

  • Steal: "casually acquired"
  • Sex: "hide the weenie/laying pipe"

Can't think of more examples off the top of my head but euphemisms are a funny way to develop inside jokes and introduce vernacular into groups that can get a lot of mileage

Double Entendres

A double entendre is: a word or phrase that is open to two interpretations, one of which is usually risqué or indecent

A lot of double entendres can also serve as euphemisms as well

Example 1:

Dance partner: VRX I'm glad I get to dance with you tonight I want you to "throw me around"

Me: I'm glad, too, cause I like to go deep on you (my dips with her get really low to the ground)

Example 2:

Dance partner 2: sorry VRX, I didn't mean to jump on that dip

Me: I know, I'm perfectly capable of getting you off [the ground] on my own

Topic-Changing Devices

There are some literary devices that use other words to convey points and often times these devices cause people to think about other stories or topics and even though you're not outright talking about these things, often facilitates conversation into other fun areas and shift topics in a fun way

Ever wonder how girls are like "and somehow [this guy and I] ended up talking about xyz?" This is largely how


Simply comparing different things with "like" or "as"

"This is like watching paint dry but worse"

"She's dumb as a retard with brain damage"

Not much to similes besides the "like" or "as" comparison


Metaphors are: a figure of speech in which a word or phrase is applied to an object or action to which it is not literally applicable.

Basically like similes but without "like" or "as"

Example 1: why are you going for her, she's such a whale, dude

Example 2: bro you're a bum, get a haircut and take a shower already

Example 3: I'm a complete slut for tacos

Metaphors are good because they often take conversations in wildly different directions with minimal effort, thus getting you away from boring "how are you? how is work? etc?" conversations into other stories and other life experiences

Metaphoric language can also move topics forward sexually without actually talking about sex because it's not literally applicable but still conveys logical meaning while branching to target topics. Metaphors can be used to deliberately change subjects if you're savvy about it

Example: That cocktail was orgasmic

Example 2: (girl sends you a picture of a really nice car) stop sending me those pics, Sarah, I can only get so hard


Analogies often have more practical value than entertainment value but a good analogy with will either make you more interesting or make people laugh depending on the contents

Example of a girl dumping a "good man" for a fuckboi and then trying to branch back to him:

"That would be like leaving a stable job with good pay and benefits for an exciting side gig that predictably but suddenly falls apart a few days later and then trying to get back your old job a week after quitting"

GOOD analogies are hard to pull off but if you can pull them off people will be more inclined to hear you speak about other things

Additional Techniques

There are a few conversational techniques that have almost nothing to do with reality but nonetheless make you an exciting conversationalist because they are funny, entertaining, and creative

Usually they contain some degree of creative fiction mixed with non-fictional details

Can lead to some high-mileage inside jokes if executed properly


For lack of a better term this is what I'm calling this one. It's short of role-playing because it's not quite role-playing

This is essentially the type of making shit up along that lines of "it's 11:11 make a wish" and "5-second rule" or "you made eye-contact with the other dude in the threesome, now you're gay"

Example: "bro, three chicks in a row said 'no' to dancing with you, you have to walk into the ocean with your clothes on now"

Example 2 (texting): I saw this cringe meme scrolling reddit just now, so you have to see it, too *sends pic*


Role playing is basically just inserting yourself or others into a suggested frame of reality with no apologies or explanation. Just act like that's how it is and roll with it.


A chick friend asked my guy friend what happened to his hand (it was bandaged). He started saying that he hurt it because xyz

The female friend alluded he lost a fight and my friend started giving a lame response back so I interjected with role-play bait

Anecdote of that roleplay:

VRX: nah he just had a really aggressive nut

Everyone started laughing and they ate it up and played along.

Him: yeah this was my 36th time jerking off today

VRX: If that's how your hand looks I don't even want to know how your dick looks

*Chick laughs a ton*

Him: yeah it's just completely raw right now I had to slap on a whole tub of vaseline

Roleplay is very versatile, it should however make sense why you're saying things. Roleplay that is too far removed from the situation at hand would require explanation which ruins it. It should be simple and relatable enough for the conversation participants to grasp and immediately play along with

Sometimes women won't immediately realize what you're doing and a quick one-liner "yeah you have a x because you did y" connecting the topics will make them say "oh" and give a face and then they'll usually say "yeah..." And jump right into the roleplay at that point

Example 2:

"Oh no this is our first fight, I'm keeping the car when we get divorced"

Example 2 is push/pull roleplay


Banter is: basically playfully giving other people shit, essentially a form of teasing


*Someone puts a lot of salt on their steak*

You: do you want some steak with that salt?

Example 2:

*Friend Freddie who has a habit of fucking things up is present when you make strategy and you say:*

"Alright, no one pull a Freddie Jenkins this time, just stick to the plans"

Example 3:

*Clumsy chick apologizes:*

It's okay, I'm still learning how to walk, myself


Reactions and Continuity

Nothing kills a good conversational moment like a reaction that doesn't keep it going long enough


Good reactions fuel the listener's or co-conversationalist's commentary to keep the conversation not only lit but potentially more animated

Having fun reactions will accomplish this


Friend: dude, why the FUCK did he think spanking her butt in the middle of church would get him laid?

You: that's what I'M SAYING


You: Dude, that was WILD, I've never seen anything that retarded in my life

Common go-to examples:

  • No shit
  • That's what I'm saying!
  • Hell yeah! / Fuck yeah!
  • Dayuuuummmm
  • Why would somebody do that?
  • What the fuuuuUUuuck
  • Dude that's fucking retarded

There are more, just note what people's good reactions tend to be and keep them in mind


These are mostly just small statements that are essentially reactions to keep a conversation going

Example: I could see why he thought spanking her ass next to the pastor was funny, but like man, he should have just snuck a handy in the pews like a normal person

Continuity can be achieved through a lot of different literary devices as well, it's just any creative bridge to keep the conversation flowing that is more rich than a quick reaction and in itself can lead to additional conversation


Story telling is a good way to convey narrative information about yours or someone else's life. Can be drawn out or brief depending on the richness of the story.

GOOD stories usually incorporate elements of foreshadowing, pausing, answering listener comments mid-story, keeping flow, using the other literary devices already mentioned, and maintaining pace and flow based on audience reaction, and other high verbal IQ skills

I'm not the best story teller. There are plenty of guides and how to structure a story online that would better explain story telling.

Asking Listeners Questions

This is old but gold. People love to talk about themselves. If you have nothing else to say you can ask people questions about them or get people talking about their life

A person can spend an entire conversation talking about themself and walk away feeling like it was a great conversation.

Usually at some point people will say "enough about me what about you?" You can also use that line if someone has asked you a lot about yourself already or if you've caught yourself talking about yourself too much

Closing Remark

Learn from stand-up comedy

Shout-out to @typo-MAGAshiv and @MentORPHEUS for pointing out one of the most powerful examples of advanced conversation skills to learn from.

Watching/listening to the routines of renowned comedians is a phenomenal way to see a ton of these techniques in real time and executed well at that, too.

I'd recommend watching a few comedians with varying styles of comedy to see the flexibility and application of expert conversational skills in substantially different ways