Cavey’s Guide: How To Chat-Up A Woman


Men are apparently triggered because they feel women make it all too difficult to have a conversation with them, especially when they just start talking. Guys, let’s be honest with ourselves. If a woman hits you up with half the lines we use to try to get them to engage with us, would you respond?…


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Men are apparently triggered because they feel women make it all too difficult to have a conversation with them, especially when they just start talking.

Guys, let’s be honest with ourselves. If a woman hits you up with half the lines we use to try to get them to engage with us, would you respond? On second thought, scratch that, because all a woman needs to do is look in our goddamn direction and our brains tell us she’s saying, “oh baby, why are you still sitting over there instead of talking to me?” Given there are times that’s true, but they’re as common in Nigeria as an honest politician (plus there’s the slight issue of guys not being able to hear what a woman’s screaming with her eyes and we’d say something as brilliant as “but why didn’t you say anything?”).

On some days, I actually sympathize with women. When I remember that y’all involuntarily commit murder monthly, have to deal with being sat down for years just to get your hair done (thank God for wigs now!) and face huge challenge of finding the right foundation that’s the right balance of matching your skin and still managing to look natural but beautiful enough, I thank the Y chromosomes in my dad for not doing a Buhari that faithful valentine’s day when he was with mother.

Anyways, I may not know a lot about talking to women but I’m going to share a few things I believe every guy ought to know because, they’re textbook ‘Chat Up A Woman 101’.

Lesson 1: Not every woman is going go vibe with you—immediately

This is not to crush (y)our fragile ego(s), but it’s the simple truth. Do away with your she’s-kukuma-stupid-and-not-even-that-beautiful mentality and accept that maybe, just maybe, she’s not just feeling your vibe. Sometimes, it’s not even because you did or said anything wrong, she could just not be having the best of days. Imagine someone sliding into your DMs just when you hear Wenger has signed a new contract, Sanchez’s medical with Bayern is booked and Cazorla has ruptured his ACL (and she has a picture of Cesc lifting the EPL Trophy as her avatar). Even if you know she’s had a good day and she’s not being responsive, that’s okay. Like we tell ourselves, there are other fishes in the sea.

Lesson 2: C is for confident, not cocky

See how lesson 1 ends with ‘immediately’?. That’s because I know I can get 8 out of 10 women to talk with me and they’d not be able to get enough if you are observant enough, you’d know the right time to take your shot and you’d bag it. If you’re not a dick and you take your L graciously the first time, it’s very possible that a few days/weeks later, she hits you up. Strange things do happen.

But more on the lesson 2: It’s important you don’t come off as cocky (or worse, entitled). She does not have to respond to you. She is not privileged to have you texting her. And she will definitely not regret replying you in monosyllables. Even if you have thirty billion in your account, ATMs don’t always respond to you. Sometimes “your financial institution is not available”.


PS: The real lesson 2 is struck out.

PPS: 8/10 because ‘confident’, not ‘cocky’

Lesson 3: Possible (girl)friend, not candidate for employment

“Tell me about yourself”

Really, guys? Really? We’re in 2017 and you’re still asking this?! Barney Stinson didn’t act straight for this.

Fam, there a lot of other ways to get a woman to open up to you AND frankly, what’s the rush? Maybe it’s just me but once I know your name, I’m good. Any other detail ‘about yourself’ I need to know would come in due time, so cool it fam. I know you’ve been single for a minute, but just take it easy. There’s nothing attractive about a desperate man.

Lesson 4: I am not my tweets

Neither are certificates the true measure of a person’s intelligence/competence, so why do multinationals ask for your resume before scheduling an interview? You can’t be calling women bitches, dragging people, being involved in one tweet fight or the other, living recklessly and come and be saying “I’m not my tweets, I’m greatly misunderstood”. GTFO with your misunderstood self.

Lesson 5: Little drops make a puddle before an ocean

Translation: go slow, take it easy. You put the tip in before you put the whole thing in innit? Can’t be telling her, on day one, where you want to get married, how many children you want to have, and how you believe a woman ought to behave in a relationship. And my personal favorite: “so how far have you gone with a guy?” Boy, you lost your claim to being a man the moment you thought it was appropriate to ask that.

Listen, you need to make her comfortable talking with you, so go for light subjects and then build from there. Talk about the day’s subject on twitter, skim through her tweets and throw in a few experiences in relation to something she tweeted (be smart in your selection), be funny (don’t be a clown), casual, don’t get to engrossed with yourself and give her room to speak. Don’t be upset if she doesn’t reply immediately (she may be busy). Reply on time. Few things are more annoying than an aired message, but if she airs yours, take it in stride. (Yup, you read that right. Or do you think you’re the only one texting her?) Find something you have in common and work your way from there. Nothing in common? Wonderful. Inquire about her habits and find why they intrigue her.

The point is, getting her to hold a conversation with you isn’t a problem, you just have to know how to lead her there and it’s your job as a man to lead her there. Once she’s there, na you go dey run sef. But what do I know? I don’t know how to talk to women.

Guys, how do you do it? How do your DMs stay popping? Ladies, what do we have to do to keep the conversation alive and lit? Please teach us by leaving a comment.


  1. Nosa
    Few things are more annoying than an aired message, but if she airs yours, take it in stride. (Yup, you read that right. Or do you think you’re the only one texting her?)……Well, is she the only one i’m texting too

    Personally, I find it distasteful to air someone, whichever party does it, a simple “i’m busy” or something is okay.

    While I may not agree on smaller parts of this article, I get the general theme.
    “Lose your entitlement mentality”. I get it.
    But I can’t help but feel like (I COULD BE WRONG THOUGH) as this article wants guys to lose that sense of entitlement, it just subtly reinforces the sense of entitlement for the lady. The undertone is littered throughout the article and I don’t think the author intended that.

    Because i’m pretty sure someone will later in the comment section say something about “guys being lazy this days when chatting up a lady and how blah blah”.

    As for how I do it and manage to keep my DMs faux-popping despite never sending that first message, well, in the famous words of Alakija, “NA GOD”,

    1. Cavey Post author
      Well inasmuch as a lot of men don’t like to hear this, it is OUR job to work at getting a woman. Not saying this is a pass to be downright petty/rude (hey Black Chyna) but they do have a stake to be a wee bit entitled. Men should chase women, that’s the way it should be but what do I know? *shrug*
      Here’s your umbrella for being first ☔️
      1. Nosa
        It is our job to work at getting what we want, That shouldn’t just apply to one gender in this context.
        Nobody has a stake/right to be entitled, this isn’t 1578.
        Men should chase women, Women should also go after the men they want (fuck society).
        Yes, the nature of what we do to get a girl is different what a girl will do, I know that. But their work doesn’t end at looking good and showing up.
        1. Cavey Post author
          No one’s saying you shouldn’t go for what you want, but certain things/roles are defined but hey, if you’re into a girl coming on to you and all that, that’s fine. Lemme just ask this:
          How would you react to your girlfriend proposing to you? If you can’t imagine that, then it’s the same; it’s your job to talk to her, it’s your job to put in effort and she has the right to be (using the word loosely), ‘entitled’.
    2. Morris
      The undertone is littered throughout the article and I don’t think the author intended that.

      Lol, Yes he did!

      Cavey, I love you!!!

  2. Taiwo
    “so tell me about yourself”

    I really don’t know how these series of words are allowed to come together in a sentence… It’s a red flag for ‘boring conversation coming through’ because nothing that I would say will lead to anything great to talk on.
    “I studied industrial chemistry…”
    “Oh great! Chemistry… You must be geek.”

    What i always tell my guys is to chill. Think of all the potential guys that are on her case and chill. Take a big old breathe and friend zone yourself. Talkabout shit. If you know her on a platform via twitter… Even better, people ARE their tweets. So you kinda know her interests. And once she’s gotten used to you (it doesn’t take time) you jump out of lane friendzone like the boss that you are with a well timed “I really like you… Would you like to see sometime?”

    1. Cavey Post author
      I howled at ‘crickets’ ????
      I’m not a huge fan of ‘playing friend’ till the ‘right opportunity comes’ ‘cos that’s a different ball game but I do agree that you have to be somewhat ‘friendly’ with her before escalating things. There are subtle ways to be friendly and keep her comfortable and still not get sucked into the friend zone but I get the general idea of what you’re saying. Thanks for your candor, Taiwo.
    2. Cypher
      Yo Bruhhhhhh that theory of yours about friendzoning yourself and bossing out is really not a great one. Quick example, I’m talking to a chic right now and she’s telling me the reason why she hasn’t been able to have serious feelings for me is because I came as a friend and not with the real intention. This is not the first time I’ve gotten that type of talk. Doesn’t mean I’ve not gotten hooked via this though, it’s just that the ‘coming as a friend’ trick works with a very slim time frame that when the millisecond to shoot your shot is missed, you’re in the friendzoned forever. Fam the only way out of this is by the grace of God.
  3. U2
    1) There’s a damn thin line between confidence and cockiness…
    2) Miss me with that feeling of entitlement. Both genders. I think it’s plain rude. Matter of fact you should only feel entitled to inanimate objects.
    3) “Tell me about yourself” stresses me out. Like I legit go blank. And I start thinking do I even know who I am? And that just stresses me out more and I stress eat. So I go grab something to eat and probably lose interest in the poor guy while at it…
  4. Tori
    “Listen, you need to make her comfortable talking with you, so go for light subjects and then build from there”

    – most valuable lesson in this post!

  5. Funmi
    If you need to work this hard, read a guide, fast and pray to maintain a conversation, nigga she doesn’t like you. Move on.
  6. Roy
    “How do your DMs stay popping?”

    For me, if somehow after dropping my weak lines via texts she does agree to meet up (or we have a real long phone convo)…….*in the words of Jesus Christ, my Lord and personal Saviour* “It is finished”

  7. OluOlu
    I go with the first thing that comes to mind, usually something random. It’s a gamble, so whatever the outcome, I’m cool. When it works, it works well.
    Sometimes, it doesn’t work because the girl just doesn’t get what you’re trying to say. Like this one time the conversation started out nicely until I said I was going to take her on a Caribbean cruise. It was a gruelling 5 minutes, trying to explain what that meant, after which I excused myself.
    Other times the fault is mine and being able to quickly interpret the look that says ‘are you really that stupid?’ allows me to either change tactics or vamoose.
  8. Morris
    Oh Cavey, this was definitely a good article, Loved it and laughed all through.

    Yeah, people still say ‘tell me about yourself’, sigh, I don’t think i have ever lovingly answered that question. I don’t judge you because of it but i definitely let you know it is ‘inappropriate’, you gotta do better.

    Lesson 2, part two was my best.

    As for the ‘airing’ part, (i did not know this was a slang), whether male/female, i have decided i cannot come and die. I hate notifications, so i read first, and if unfortunately i am too busy, i respond whenever i remember. Na me get my profile o, even on watsapp. I have read it, oya come and kee me.

  9. RebelAtHeart
    It’s either an abysmal low self-esteem or a terribly misplaced sense of priority, or a sick admixture of the two, that would warrant a man, or a guy, to go through the long, unnecessary hassle of knowing the right things to say when conversing with the opposite sex.

    How do we know what is right and what is wrong, especially as both are very relative and arbitrary terms?

    Guys, we need to stop apotheosizing women. They have buttholes like us. They shit. They pee. They are not gods. And, like us, they are flawed.

    What is wrong also with asking a lady to tell you about herself. Are you to ask her to tell you about her mother or her great-grandfather?

    There are a varied number of creative and comical ways to get a girl talking about herself, and it’s always good to ask regardless of what you might have inferred from her tweets or blog and whatnot. People generally like to talk about themselves – a guy just has to cash in on that innate creaturely narcissism. Frankly, when one overthinks what is proper or improper to say in a conversation, chances are you’d come across as wooden. It’s better to speak with a nonchalant and yet attentive carefreeness. Be amoral and don’t allow all these nonsense social, conversational norms to keep a lid on you, and you will be fine.

    1. Cavey Post author
      Oh dear Rebel ????
      TBH, with the way you started out, I was expecting a more…intelligent comment but it’s calm.
      I get that there’s no ‘script’ you ought to follow when talking to a woman but there are DEFINITELY things that are and are not appropriate when talking with a woman (gentle reminder: this is someone you just met). Can’t go telling her about your body count and how big your whip is now can you? I’m not sure this article in any way ‘apotheosized’ women (lol! I didn’t even know what that meant before today) but yeah man, we know they’re human and all that but thanks for reminding us. Oh and like you said, people generally like talking about themselves (IF THEY WANT TO) so why again do you need to probe before she talks? But thanks for reading and sharing your opinion ????
      1. RebelAtHeart
        It wasn’t as intelligent a response as you thought it would be because I voiced a contrary opinion? If this isn’t the classic stock-in-trade of one unable to accomodate a dissenting opinion then I don’t know what it is.

        And yes, this article apotheosizes women, albeit implicitly. How many e-manuals have you seen instructing women on how to hold conversations with men? Such are virtually as non-existent as is honesty in the collective souls of Nigerian politicians. Only things we see are articles that lecture males on how to please a woman — as if we exist to worship them.

        My point is we need to stop making these women feel entitled. It’s cringeworthy having to follow a manual in order to chat up a woman. Nay, not cringeworthy, but pathetic!

        As regarding what constitutes as inappropriate in a conversation, like I said, it’s impossible to DEFINITELY assert what’s acceptable and what’s not, ‘cause what one lady might find offensive, another lady might giggle at. Things of this nature are relative and a hit-and-miss affair.

        And, of course, only a bipolar patient would begin bragging about the size of his pecker to a girl he just met. I think that example of yours is what rhetoricians glibly call “reductio ad absurdum” – reduction to the absurd.

        I still maintain that there’s nothing wrong with asking a chick to tell you about herself. If anything it proves or at least gives the appearance of your being genuinely interested in her.

        Honest to God, I think you folks are a tad uptight and need to chill.

        1. A
          funny enough i don’t find guys asking me “tell me about yourself” boring, it just opens the door for my chatty self to flourish.
  10. Jojo
    I utterly detest the “tell me about yourself” line cos it makes me panic, like I’m still trying to figure myself out don’t stress me out. I don’t have a problem with hitting a guy up first. In fact, it’s not a problem at all. But when I hit you up and try to converse and you don’t have the decency to keep the relationship alive that’s where I’ll have a problem. I’m not hitting you up cos you’re the love of my life im hitting you up cos I’m trying to know you. It should now be considered OUR responsibility. I could easily be staring my walls down if you want to air me in the middle of the conversation than be with you.
    1. RebelAtHeart
      “I’m not hitting you up cos you’re the love of my life im hitting you up cos I’m trying to know you”

      Ain’t this one hell of a paradox? You hate when a guy – who’s probably only genuinely interested in you – ask you to tell him a few things about you. And yet, you say you hit up a guy so you can try to know him.

      Pray tell, how do you plan on knowing him you unless you seek to plumb the depths of his soul with curious and friendly questions?

  11. Sussy
    @rebelatheart the point is you just MET the person, with time and effort you will probably hear her life story.
    Guys we know you are excited but chill up a bit, from my experience when a guy is all anxious to know my life story at our first convo, the excitement doesn’t last.
    I met a guy some weeks back, gave him my number then he called that same night around like 10pm on a work night, we spoke for like 40mins then I told him I needed to sleep(not that I wasn’t feeling him, I was just genuinely tired) and he goes so you don’t want to open up to me (he was even asking my age/relationship status). The next morning when he called, he kept accusing me of running away the night before that he doesnt like to waste time. Oga o we just met, there will be more conversations to see if I tick all your boxes, lets just strike a balance.
    1. RebelAtHeart
      Lol. You sure that guy was not a newly released convict who hasn’t felt the touch of a woman for decades and who so desperately needed to quell the fire in his loins? Ah! Such desperation!

      Sussy, I’m new here. Do you mind orienting me with how things work here?

        1. RebelAtHeart
          Thank you, sensei; first of all, I want to learn the tricks in getting one’s material published. I forwarded a prose to the moderators some weeks back, but I haven’t heard diddly squat from them.

          Also, I want you to tell me who’s the hottest cake here. Who are the slayqueens? Who are the finest chicks? Are you one of them? ????

          1. Sussy
            @rebelatheart I responded to you earlier but unfortunately my comment wasn’t published. You can always look through archives to check for Funmi’s post on the don’ts of getting a post published.
            Also as for hot chicks/ awon slay queens inquire from the guys here lool
  12. G B
    After I googled the big words, I agree with @rebelatheart.
    Personally, I don’t even bother to DM women anymore on IG or Twitter. Forget about how asking them “tell me more about yourself”, sliding into the DMs itself feels like you’re applying for a job! To start pacing and rehearsing lines etc, I no dey do, abeg. It’s only job interviews I will ever bother preparing for that way (even that one, sef, na stress – I ended up with my first job while I was wearing boxers over a phone call after all).
    Yes, some women seem to believe they ARE on a pedestal. Ask yourselves how many girls’ profiles you’ve seen where It Is Written “don’t start a conversation with ‘hello’ or ‘hi’ or get blocked” or something similar. It’s like these magnificent creatures think, “I’m allowing this dude to talk to me, so he owes me!” A girl even once replied “ur wlcm” to my “hello, nice to meet you” if this helps illustrate my point.
    Me, I will probably still ask that question in the future. If she’s interested, she’ll “forgive” me and say something random like “I like reading and Candy Crush”. The conversation will move ahead.

    We won’t vibe with everyone, anyway.

    1. Sussy
      Well you have a point that it is difficult to start up a first convo but if it flows it does and if it doesn’t well you can try again another day. Is starting up a convo really as hard as an interview though ????
    2. RebelAtHeart
      Exactly, man. These guys just don’t get it. We know women have bottom power, and it’s no secret their hands most often pull the strings when it comes to sex. We know also that by virtue of the existing societal norms and “biological imperatives” perhaps, that women don’t have to do the chasing, but even still, a guy must never appear needy or to be living to please a woman, otherwise she would know she has the upperhand and the “Shakara games” would ensue.

      Robert Greene talked about this sort of thing in his book, “The Art Of Seduction”. The often amoral, calculatedly nonchalant, “non-needy” guy who doesn’t obsess over what’s right or wrong in a conversation with a girl, the one who forays the high hills and lowly meadows in a convo, the one who doesn’t mind to chip in some mordant humour and some occasional sexual innuendos, is usually the one who leaves the ladies WET.

      Girls naturally are used to guys bending backwards for them, guys that would memorize lines and work on being on their best behaviour. When these same girls meet a guy who just doesn’t give a fuck, they get curious, they begin to feel self-conscious and think perhaps the fault is from them. That, my friend, is when the guy swoops in like a giant eagle and, in Donald Trump’s words, not mine, “grab that püssy by the short and curlies”.

  13. RebelAtHeart
    , I figured you must have encountered a let, for I know I’m too hot a guy for a lady to air. Don’t take me serious oo – I fear alcohol hold my faculties in its throes. ????

    Okay, thanks. Off I go to suckle wisdom from Funmi’s bosoms!

    I’ll be in touch, Sussy. By that I mean I’d send a private message. I hope you would respond. Did I tell you the name “Sussy” comes across as a bit of an aphrodisiac? It does! In another life should TNC exist, do well ma’am to shirk away from monickers that are pornographic by virtue of sound. ????

    Now, in preparation for our private correspondence, all I have to do is mentally condition myself beforehand to not fall into the mortal crime of asking you “tell me about yourself”. ????

      1. RebelAtHeart
        How are you doing this fine evening, Sussy?

        I tried sending a message by clicking on your profile, only to realise that you’re commenting as a guest rather than as a member. I can’t forward a message unless you’re registered as a member on TNC. Would you please be a darling and rectify the situation? ????

    1. Derrick
      Heaven knows i like this guy rebelAtheart.
      Dude you’re hilarious.

      He even went on to demonstrate that guide no ‘EPP’ anybody.
      See the way Sussy was smiling.

      Just Talk, if she likes you, great! If not move on bro.

      Rebel Indeed ✌

      The big big grammar sha ????????

  14. Ramatu
    I think one of the worst things is the ‘Tell me about yourself’ line. It is such a turnoff. I will chat with any guy who makes me laugh or presents me with a challenge. Almost every other thing may present slow responses from me.
  15. Buzz
    Never had much success with sliding into DMs and such (probably too busy getting lost in the twitterverse and I’ve always wondered aw peeps do that) tho I’ve had way too many successes getting girls I meet in person. And I’ve learnt just one thing, women love mystery and they are always attracted to a mysterious man, dunno why maybe it’s a genetic flaw, the always wanna know what makes you so different, and why you’re not fawning over them like the rest of the world, now add to that mystery a quick and witty mind ( complete recipe for mind blowing experiences). scored me quite the number of women But like cavey said-what do I know- but then again different strokes for different folks .

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