How To Keep A Conversation Going With A Woman (With Examples)


Hey there! What’s up?

Wanna learn the secrets of how to keep a conversation going with a woman in a way that is fun, playful, and flirty!

I understand that talking to attractive women does not come naturally to many of us. In fact, a lot of energy is being spent just to summon up the courage to approach and talk to a girl, and by the time we start a conversation, we find ourselves running out of things to say to her.

But learning how to how to have a conversation with a woman isn’t as difficult as many of the dating expert would like you to believe. In fact, making small talk fun, playful, and flirty is super easy, if you know how.

Here’s one thing you always need to remember when interacting with women: if you notice that you’re asking her a lot of questions about her college, parents, pets, jobs, or any other type of questions that may resemble like a job interview, stop it; otherwise you’ll quickly wind up in the friendzone.

In this post, you’ll find nine effective ways to start a conversation with any women — including beautiful ones — and keep it going on, while also making her laugh, giggle, displaying that you’re interested in her, and escalating the conversation to the “sexual level” — taking her back to your place.

Eight effective ways to start a conversation with a woman and keep it going:

1. Avoid questions; make statements.

I’ve noticed that a lot of guys, as soon as they initiate a conversation with a woman, bombard her with questions after questions, hoping it’ll engage her and she won’t leave. I’m not saying it wrong to ask her questions. In fact, that’s how you find out interesting things about her, but often times, most guys make the mistake of asking her questions that sounds like she’s on a job interview or something, which will only make her feel bored, and want to leave the conversation.

Plus, I’ve also notiche that, after getting her response for their question, immediately jump to the next, without even trying expand on her response, or the topic she clearly seems to be enjoying talking about.

Try this instead:

Next time as you’re interacting with a woman, try to follow up her answer with a statement,  rather than asking her another question.Not only doing so will show her that you’re listening, but you’ll also connect with her on a whole different — deeper — level and probably lead the conversation towards fun and interesting topics.

Here’s an example on how to make statements when responding her:

You: “So do you have any pets?”

Her: “Yes, I actually have two of the cutest cats in the world.”

You: “Um… so you’re one of those girls with cats, eh? (sly smile)”

Her: “Haha… stop it… no, I’m not one of those crazy dog women… I just love cats.”

You: “They say people who like cats tend to be more independent than dog lovers.”

Did you notich that by following up the question with a statement, and not asking another question, you’re quickly able to expand on a simple topic (pets) and bring an element of fun and banter into the conversation.

2. Qualify her

As you’re interacting with a woman you, if sense there’s a good connection going on between the two of you, do not be scared of breaking the rapport, or saying anything that you think could damage your chances with her.

A lot of guys, I’ve noticed, often tend to stay on the safe topics — boring topics — to avoid breaking rapport. Unfortunately, playing it safe doesn’t always work for him — it becomes extremely difficult to escalate the conversation to sexual topics — and he often ends up making her feel bored (even if she was interested in him before).

Try this instead:

Once you sense there’s a spark of chemistry between the two of you, immediately begin qualifying her with statements, or questions that puts you in the role of “the selector,” and disqualifying her as a potential lover.

Here’s an example of how to qualifya girl during an interaction:

You: “So do you have any pets?”

Her: “Yeah, I have three of the cutest cats in the world.”

You: “Um… I think we would never get along. I’m a dog person, and what I’ve heard is that dog and cat owners often tend to have intense sexual chemistry, but disagree on every other possible point.”

Did you notice how you’re able to take a “safe” topic (pets) and bring an element of sexuality into the conversation? And by making the statement “we would never get along,” you placed the burden of approval seeking on her.

3. Talk about your passions.

Often times, most guys get stuck in “interview type” topics with a woman — job, career, college — that they rarely get a chance to display their passionate side to her. They keep on ranting about mundane topics just to keep the conversation going and hoping she won’t leave the interaction, but wind up making the woman look at her wrist watch for the 20th time under a minute.

Try this instead:

Go and ask any woman what personality trait she finds sexy in a man and pretty much every one of them will tell you the same thing: passion. So the next time you’re interacting with a girl make sure to talk things you’re passionate about.

Whoever said, “Enthusiasm breeds enthusiasm,” must be 100% right. If you’re passionate about something, you can take a mundane topic, like cooking, and expand it to have a more stimulating conversation with a woman.

Here’s an example of how to talk about things you’re passionate about:

If you love travelling, let her get a sense of what really excites you about seeing the world. If you are into building a business, let her see your entrepreneurial spirit shine through. If you love music, movies, or art, don’t be shy and hide it.  Express it instead. Now, of course, expressing doesn’t mean you brag endlessly about your knowledge of these topics, but you must explain what is about them that really makes you tick.

Women want to be around with men who know what they want and go after it — a driven man. So let her see that aspect of your personality by talking about things you’re passionate about.

4. Improvise.

One of the biggest problems many guys have is “running out of things to say” to a women during the interaction. This often happens for two reasons: either the conversation stalls out because they don’t know how to change a conversation thread, or they don’t provide enough threads for her to latch onto and flap her gum.

Try this instead:

Next time you’re interacting with a girl, try to give her several different topics when comosing your response to her question so that she can latch onto any one of the topics she can relate to, or have knowledge about, and keep the conversation going.

Here’s an example of how to construct your response to her question:

If she asks you, “What’s your favorite sports?” instead of saying, “I love to play basketball,” which limits the conversation thread to just one topic (basketball), try to compose a response that includes multiple conversation threads, like “I love basketball because it’s physical sports, and I get to exercise, de-stress, while also have fun hanging around with my buddies. What about you, which sports do you play to have fun?”

By constructing your response with multiple topics — basketball, exercise, friends, sports — you give her a lot of conversation topics to latch onto and make her easy to follow up with any one of the topics she could relate to, or enjoy talking about, and keep the conversation flowing. Now, she’ll be able to tell you a story of where she likes to go to exercise, and where she likes to go to hang out with her friends, which she’d never have been able to do if your response contained only one topic, like “I like basketball, and you?”

And when she’s telling her story, make sure to listen carefully to what she’s saying (a lot of guys don’t do this; here’s your excellent opportunity to stand out from the pack), and when she is finished talking, latch onto any one of the topics she shared with you, and follow up by constructing your response like I demonstrated in the example above to keep her glued to you.

For example, if her response is something like, “Hey, I love cooking too. My mom taught me how to cook, and now I even find myself watching those stupid cooking shows on TV,” you can follow up with something like this, “Yeah, I feel the same way with those travel shows on TV, I start watching them and get sucked into all of the amazing locations? Where would you go on a vacation if money wasn’t a problem?” instead of sticking to the same cooking topic.

So do you now know how easy it is to transition from one conversation topic to another just by taking one word (TV) and improvising it off to a completely new topic? Most guys have a false impression that beautiful women don’t want to talk to them. That’s not true. Beautiful women love fun, playful, and flirtatious conversations just as much as we men do. But only a handful of men know how to get a sneak peek into women’s personality with their effective communication skills.

There are two reasons why most men fail communicating effectively with women. It’s not that they run out of things; it’s not that they don’t know what to say next. They let their shyness, anxiety, nervousness, and other insecurities prevent them from displaying their fun, playful, and sexual side to women — especially to beautiful women — because, in their own mind, they think doing so will make the girl feel uncomfortable, and so they stick to friendly, normal, and boring get-to-know-you topics.

Plus, these guys don’t know how to talk to her in a way that she likes to respond. It happens all the time, but you can change your approach by using any of the conversation tactics mentioned in this article to strike up a stimulating conversation with any woman and keep it going.

5. Tease her.

Most inexperienced guys put women — especially beautiful women — on a pedestal and treat her like a royalty. They don’t want to offend her; they become obsessed about coming up with a perfect line or joke to say to her to keep her hooked, or to look cool, but doing so will quickly stall out the conversation.

Here’s a fact you must know that most dating gurus never talk about: A woman wants to be around with a fun-loving guy because they’re, and we all are, still children at heart. Even though most of us love having a stimulating conversation with others, when we’re out on a date, or at a bar, we just want to let our guards down, relax, and have a good time, and forget about all the worries and stress in our life. And the best way to do that is to keep the conversation playful, fun, and flirtatious.

Try this instead:

The main reason why you must, or learn to, tease a girl is you want to create a warm, fun, and playful atmosphere around you so that she can loosen up and let all her guards down, and be herself and open up to you.

Teasing means being silly with a girl. It means treating her the same way you would your little bratty sister; it means having a conversation with her in a fun, playful, and flirtatious way.

And if you want to learn how to tease a girl, you’ll have to drop off your “cool guy” image for a while, and just relax and have fun with her. You should not be afraid of being a little goofy.

Here are a few examples of how to tease a girl:

  • Imitate her.
  • Get ready to give her a five but then pulling away at the last moment almost as if you changed your mind
  • Suggest she’s coming on to you.
  • Tell her an overtly exaggerated lie, and then pick on her for believing you.

These are the same sort of things you did on the playground when you’re a 6 years old kid. They worked then, and they’ll work now too.

6. Use “cold reads.”

We men love to talk about “surface level” topics, like facts, figures, stats, and events. While all of these topic areas can make up for a good deal of materials of your conversations, they often tend to limit you from entering into areas that could easily spark passion and fire — a lot of emotions — in a woman.

Women get their kicks from talking about the mystical — “deeper level” topics. They love to delve into the emotional meaning behind those facts, stats, figures, or other surface level stories. And if you never give her a hint that you’re actually capable of communicating on a much deeper level, then you’re definitely missing out on a great opportunity to stand out from the crowd.

Try this instead:

Next time you’re interacting with a girl, try using “cold reading” technique (shared below) into your conversation, which will allow you to easily delve into deep topics and get her to share you some of her buried — and numbed — emotions.

Cold reading is a technique of letting a girl know that you’ve noticed something intriguing about her, by making your observations, and then having a deep conversation about it. So if she brings up a topic about her ex or a guy she knew, here’s how you can use cold reading technique into your interaction:

You: “I can tell you just by the way you’re talking to me that you’re the kind of girl who goes out on a lot of dates but has difficulty finding someone you’re actually interested in. And then when you finally find that person, you often lose interest very quickly.”

Her: “Yeah. That’s so true.”

You: “I bet you really love adventure. Even though it scares you sometimes, deep down you crave for something exciting. And what I feel is happening with you is that every time you meet these guys, you quickly feel as if they’re not going to satisfy that adventure you so desire.”

The above example allows you to dive deep into the mystical and the emotional, and also lets you to disqualify other guys, while also establishes you as someone who is different, exciting, and fresh, who just might be the cure for her sickness.

These are just some of the ways to dramatically improve your conversations with women. The ability to hold a fun, playful, and flirtatious conversation that takes interaction towards the end result is a skill that most guys have to actively learn.

7. Tell her good stories (putting you on a “positive light”).

When we’re hanging around with our buddies, it becomes almost a competition as to who can tell the best story. We try to tell stories that make us look the coolest, funniest, and the most alpha guy in the room. Yet, for whatever reasons, when a beautiful girl makes her entrance in the room, we totally forget to make full use of this vital skill.


A woman wants to try to figure out things about you on her own. She doesn’t necessarily trust everything that you’re saying to her, so she is trying to look for little clues that’ll help her figure out where you fit in the pecking order.

Stories are a natural way to capture other people’s attention. And if told properly, they can also act as a great tool to display all your awesome qualities of your persona.

As you start to tell a story to a girl, you need to understand that she’s not only listening to your story, but she’s also reading behind the lines to make certain judgements about you.

For example, let’s say you’re telling this story to a girl on a date:

You: “On the Wednesday afternoon last month you’re lying in bed with a hangover and someone kept knocking on your door until you finally answered it and it was these annoying religious freaks trying to convert you to some weird new religion.”

Well, while you may have intended the story to be funny farce about the annoying religious people, she has already begun to pigeonhole you as the kind of guy who gets drunk on Wednesday nights, doesn’t have a job he has to wake up for, and has no ambition to get out of bed until the afternoon. These traits will not excite her unless you’re both in college. 🙂

Try this instead:

You certainly do not want to come off as a bragging guy while telling her your stories. Any positive traits about you that you want to highlight must be hidden within a larger story. What this means is that while the story itself does not have to be positive, she must be able to uncover positive traits about you from within the story.

So let’s use the same story from above about the religious folks knocking on the door and see how we could tell it in a way that sheds some positive light on you.

You: “One Wednesday afternoon, I was sleeping late. This was like the first good comfortable sleep I’ve had in a couple of weeks as I was been busy busting my ass trying to elevate my business to the ‘next level.’ Tuesday night we scored a kick-ass contract, and me and my team finally decided it was time to celebrate. So now on Wednesday morning, I’m lying in my bed, with the kind of hangover I haven’t had in years, and I kept hearing a knock on the door. I just didn’t want to get out of the bed. Later that night I had a few more important meeting, I really wanted to sleep off the hangover so I would be in top shape to deliver the proposal. Well, the knocking stopped for like ten minutes, but then it started up again. And now they’re ringing my bell too. Finally, I threw on some clothes and headed downstairs to answer the door, and there’re these two little girls outside. At first, I was thinking they want to sell me girl scout cookies, but then one of them hands me this flyer that says ‘Let Jesus save you from your treacherous life’ and I’m thinking am I on some sort of list of something.

In this version of the story, I’ve included enough details to let her jump to the conclusion that I am an ambitious and successful businessman. But I never came out and said it. I gave her this information in the context of a story about a couple of religious nuts trying to convert me.

8. Focus on the feelings rather than the facts

Unlike men who are logical, women are mostly emotional. They like to talk about the meaning behind all the actions and the emotions (feelings) they evoke.

It is also true that the emotions that you arise during a conversation she’ll subconsciously anchor them to you. This means that if you’re talking about relationships and she starts talking about all of the bad feelings she experienced with her previous boyfriend, she’ll begin to associate you with those feelings too.

Try this instead:

If it’s true that women will anchor negative feelings to you, then it must also be true that women will anchor positive feeling to you. That’s why it’s very important to bring her into a positive emotional state.

There’s a simple way to bring her into a positive emotional state: tease her. Another way to do this is to ask her questions and make statements that make her talk about specific feelings that she has for something.

So if you are having a conversation with a woman and she tells you that she loves going snowboarding, instead of talking about all the junk facts about it, such as what mountain does she usually snowboard at, or what kind of equipment does she use (which is the kind of questions you would ask any other man), get her to talk about the feelings she experiences while snowboarding.

Here’s an example of how to bring her into positive emotional state during an interaction:

You: “Did you do anything fun last weekend?”

Her: “Yeah, I went snowboarding. I had the best time.”

You: “Wow. I love snowboarding too. I think I’m addicted to the rush I get going down the mountain. What about you? What excites you about snowboarding?”

Her: “Well I guess it would be that feeling of adventure… like going so fast, being so scared, but not wanting it to end because it feels like you’re really living.”

In this example, you took the topic of snowboard and talked about the meaning behind snowboarding and emotions it evokes. Since these are emotions are positive, you’ve put the woman in a positive mood, and she has subconsciously anchored the feeling of adventure, excitement, and not wanting it to end to you.

9. Remember the non-verbal’s

There are subtle things you can do to let her know that you’re a fun, confident man that she should feel excited to talk to. Most men skip this altogether. Instead, they let their shyness and nervousness control their entire body and the end up coming off as tense, fidgety, and even slightly awkward.

Why does this happen? you might be thinking.

Well, this happens because, while we men are having a conversation with women, often times we seem to get stuck in our head. We start to focus extremely hard on how to impress the woman, and then wind up coming across as nervous, timid, robotic, and boring.

Try this instead:

Here’s an effective tip I learned from one of the greatest pickup artists, Style: imagine that the woman you’re talking to has already told you that she is going to get naked and sprawl out over on your bed and let you have your way with her.

Now if you knew this fact, how would you act?

You’d probably be quite laid back, won’t you? You’d have a smile on your face, knowing what’ll happen later, and you would have absolutely no problem bringing out the fun and flirtatious elements into the interaction because there wasn’t a risk of rejection at all in the first place.

Well, can you imagine how acting this way can actually help you get the result that you’ve been craving so much from women? So next time you’re out, just give it a shot.

Stay chill.


P.S. By the way, if you want to learn how to effortlessly approach, captivate, connect, and date beautiful women in the streets, cafes, malls, or anywhere else under the sun (even if you’re shy and afraid in the past), then grab a copy of this kick-ass resource.

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Abishek, a "self-development/dating expert," LOVES helping men overcome their "shyness" and crush their "social/approach anxiety"... so that they can too be able to effortlessly meet, captivate, connect, and date MORE women than they've in the past... on the streets, cafes, malls, or anywhere else during the day (even if they're shy, short, ugly, boring, or completely newbie in the game)!


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