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How to Never Run Out of Things to Say with Girls

run out of things to say with girls

One of the most common questions I get (the other being – how to conquer approach anxiety, which was such a popular question I wrote an ebook about it) is:


“Sinapse, I always run out of things to say. How can I keep talking forever with girls and never run out of things to say?”


Those who know me now might be shocked to learn that I was one of the BIGGEST introverts EVER in High School (and before). I had about three close friends who I ate lunch with every day out back behind the school. We ate far away from all the “cool kids” and didn’t really engage with anybody else at all. I had a few acquaintances here and there but never was invited to the big parties and was never involved with any of the popular clubs or sports. If I talked to a cute girl in a class, the conversation would be short and awkward, and I’d find some reason to escape becase I feared exactly that – I had no “conversational fodder” to continue the interaction. If I did end up in a confined situation where I couldn’t escape I’d pretty much always end up running out of things to say.

In university I decided that I would change my sorry little anti-social behaviors, and started reading a lot of books on body language, self-improvement, social skills, and eventually, pickup. Now, I recognize the importance of the “gift of gab” or the “million dollar mouthpiece” – the ability to talk virtually endlessly and make it interesting. I can pretty much talk anybody’s ears off if I want to at this point and be cracking jokes left and right along the way. But I didn’t always have that ability to talk forever… I learned it through practice and a lot of frustration!


So I’ve put together this list of tips to help you never run out of things to say with a girl again!!

1. Lower the bar for what you consider acceptable conversation.


I used to have this problem…BIG. I thought that if I didn’t have anything witty to say, I just wouldn’t say anything at all. What happened was I was building up a lot of pressure on myself to always be witty and funny, and that ended up with lots more silence in the interaction. While silence isn’t something to be feared, it also probably won’t hook you many sets. The opposite – feeling comfortable saying nearly anything, even if it’s dumb or trivial – puts you at ease and relaxes you in the conversation. This relaxation then paves the way for humor and brilliance. It’s important to realize that the “bar” or “standard” for normal conversation isn’t very high – you don’t have to blow her away with the informational content of a TED talk or humor of a stand-up comedy routine.

2. Avoid questions. Use assumptions instead.

Questions (in large doses) kill attraction. The vast majority of most guys’ “game” in bars and clubs is to go up to a woman and ask a bunch of questions, leaving her feeling as if she’s being grilled or interrogated. Worse, these are all questions she’s likely heard from every other guy out there a million times before. Questions don’t have much POWER. The grind the interaction to a halt and you quickly run out of things to say.

Instead, make assumptions about the girl. Assumptions are win-win because you’re either right (leading her to be astonished at your ability to intuit and seemingly know her deeply) or you’re wrong (leading her to correct you with the correct information). Best of all, assumptions lead to better, longer, and more in-depth conversations than simple questions. Consider the following example:


Guy: So, where are you from?

Girl: I’m from Kanagawa, near Yokohama.

Guy: Oh cool. I’ve been to Yokohama before.

[awkward pause as man scrambles to find next thing to say]

Girl: [rescues interaction] What about you?

Guy: Oh, I’m from Toronto, Canada.

Girl: Cool! I’ve never been to Toronto but I went to Vancouver once.


[and so on…]


Compare that to a conversation with more assumptions:


Guy: You seem like an inaka girl. Maybe from Ibaraki or something.

Girl: Whaaat? Why?? I’m from Kanagawa not Ibaraki.

Guy: You just don’t seem like a big city girl, more like you’re familiar with cows and rice fields.

Girl: Heeey I’m from Yokohama, there’s no rice fields!

Guy: Oh, well I’m sorry. I guess you just have a cute country vibe. I’m sure your ex-boyfriend loved that.

Girl: [rambles on]


As you can see, the second conversation contains more assumptions which in turn lead to more emotional spikes / interesting and unusual conversation, as opposed to the first conversation which is far more rote and rehearsed – everybody has had that conversation a million times before. Simply put, assumptions drive the conversation further and you get more bang for your buck!

3. Utilize the “Big 5” topics

The “Big 5” topics – which pique the interest of women – are:




-Entertainment (Music, Movies)




If you often run out of things to say, sit down and think of two things you’ve done (or are interested in) and two things to ask (or better yet – assume of) the girl in each of these 5 categories.


At some point I’ll go into a lot more cultural detail about fashion in Japan, but this alone is a HUGE topic which absolutely BLOWS open sets. I always recommend guys check out Japanese fashion magazines and poke around on Ameblog or other Japanese blog sites and delve into fashions and subcultures you’re interested in more.


Relationships are another MASSIVE topic, and women can talk almost endlessly about them. For starters, you could discuss how her friends see her, or why she broke up with her ex-boyfriend. These often lead quickly to discussions of core values and emotional content. Alternatively, talk about yourself and your past relationships or the interesting affairs of people you know. Carl at work did WHAT with Sally? How does this girl feel about it?


Entertainment is a massive cultural force in Japan, and people often attach a lot of identity to what they listen to and consume. Is she more into Western movies, Johnny’s idols, or K-pop? Hip-hop or psy-trance? Talk about some music events you recently went to (side note – ULTRA Japan, Electrox, Summer Sonic, Fuji Rock, etc are GREAT places to meet chicks).


Travel doesn’t have to necessarily mean outside of Japan – it can even include heading over to Yokohama Chinatown for some Sholompo dumplings (yum!) or hitting up the onsen in Beppu. Either way – it’s highly relatable and easy to talk about. I sometimes chat about past adventures I’ve had around the world or even last week, and try to engage girls as well. Most often Japanese girls haven’t been anywhere more exciting than Guam or Hawaii, but travel still is associated with good feelings and new experiences. Digging up stories from their or your past will similarly dig up such emotions.


Finally – food. Everybody eats. Everybody loves food. One of my favorite “openers” is dumb but effective – a simple declaration of what I’ve just eaten. On a cold approach, it hits all the right signals – unapologetic, atypical yet totally normal, assuming familiarity, relatable. Over text it can be great as well… “When in doubt… send food pics!”

4. Emotionally Charge Your Conversations


By now you’ve gotten a sense of some tweaks and fixes to your “verbal game.” Another huge one which I already touched upon above in the “relationships” section of the Big 5, and the “assumptions” section as well, to a lesser degree, is the power of emotional content. Needless to say, most conversations women and (nervous) men engage in are highly mundane, and fail to register much of anything meaningful on the emotional spectrum. By simply moving away from these widespread and BORING habitual conversation pieces, you easily set yourself above the competition by miles.

How? Introduce emotion. Drama. It can be something real from your life or history, something assumed about her life or history, something that happened to a friend, or something entirely unrelated to either of you (hypotheticals or celebrity gossip).

Crucially, you shouldn’t shy away from negative expression. Expressions of “realness” can be incredibly powerful icebreakers, and bring the most reluctant conversational partner into the fray. Examples of this might be – stress from work, decreasing economic conditions, worries about life. The more “together” you seem to be, the more effective these are. While they may seem like depressing topics, many women – especially the most attractive – are grateful when men are able to relate to them in a REAL manner (as opposed to padding the conversation with saccharine “pleasant conversation” or endless bragging and positivity). This isn’t to say you should be gloomy or dour – indeed that would not have a good effect at all – however, injecting some real negative expression into your conversation style shows you aren’t afraid of any topic, and your life has color and depth. Would you hide the real, sometimes more negative conversation topics from your girlfriend or wife? Of course, careful not to end up gravitating towards endless whining or complaining – keep things a healthy mix of light, funny, and positive, as well as real and deep. If you find you’ve run out of things to say, throw out some drama or realness!

not run out of things to say on a date

Carl did WHAT NOW?

5. When in doubt, Share


We all know that Japanese girls aren’t exactly the most forthcoming with the great conversation topics and deep emotional intrigue. However, it can help to “go there first” and share some stories or “confess” something to the girl. Whereas before she may have been reluctant or unsure about divulging her own personal beliefs and emotional content, if you do it, it becomes okay! Sharing things gives her an easy “in” to the conversation, as well as setting the stage for her to reciprocate with a confession of her own.

Prepare 3-4 REALLY good stories. I’m sure no matter who you are you can come up with some funny, interesting, or deeply emotional stories to tell. My personal favorite stories are either related to travel or heartbreak.

6. Cut Deeper

Dorian Gray is the true master of cutting deeper, and he’ll be posting his seminal article on Cutting Deeper on this site soon.. But for now I’ll give you the brief version. Cutting deeper essentially means relating to the girl on a core, deeper level. Whereas most of the superficial interactions take place on the “information exchange” level of communication – like a computer sending packets to and from another computer – “cutting deeper” requires you to slice past this and get to the VALUES level of communication. In short, What are her values? What motivates her? What does she fear? How is she perceived, and how does she feel about this? 

Every single thing she said is like an finger that points to the moon. Men, often being socially unsavvy, stare at the finger (the informational content of what she says) and ignore the moon (the VALUES she is relating with her informational content). For example:


Her: “I love Disney!”

Here, you could get into talking about how you feel about Disney, or what Disney movies you like, or if you have or havent been to Disneyland. And that would be okay. BUT – what does the fact that she like Disney SAY about her as a person? What values could you unearth from this? Why does she like Disney and not Japanese anime? What purpose does Disney serve in a grown woman’s life?


Begin asking these sorts of questions of her – or assume it – and you will be on the road to discovering who she is, a huge key in having better dates and connecting more with girls. One way of thinking about it is if you’re a miner, you wouldn’t get caught up staring at all the inert rocks, you would dig and keep digging until you find the GOLD. In this case, the gold is the girl’s values – her essence. If you can cut deeper effectively, you will never run out of things to say on a date.


It helps to

     A. Know what you want (your values)


     B. Be non-judgmental.

how to have a great conversation with a girl

Back in my cattle russlin’ days…

7. Eliminate “transitions” and “introductions”


Introductions (on the cold approach) are overrated. Highly. I’ve pulled girls all the way back to my house and had their bra undone when they stopped me and asked “Wait. What’s your name?” Sometimes it’s after sex. The fact is, the preliminary information we deem standard introduction material rarely really gives you much insight into the girl or you, and even the less if you’re operating on the “information transaction” level of communication.

By skipping the introduction totally and instead acting as if you already know the girl, you shave time off the interaction and establish a sense of familiarity. Similarly, transitions and background information are less captivating than the meat of the story. Consider the two following stories:



You: So I have this friend, right. His name is Carl and I’ve known him for about two years. Carl and Sachiko have been dating for about six months but she’s already trying to leave all her clothes over at his place. Isn’t that weird?



You: Fucking Sachiko is really pissing Carl off with her constant attempts to leave more and more luggage at his place. I think he’s going to dump her soon. *Orders another whiskey*


Do you see how option B creates far more questions in the girls mind (and therefore far more opportunities to jump into the conversation). Who are these people? Why is he talking as if she already knows the characters in the story? Why is she leaving luggage at his place? Why is he so casual in telling this dramatic story?? Intrigue!!

8. Slice and Dice Conversations

Conversation heading down a familiar, boring path? Don’t worry about conversational flow – just cut it off and take it somewhere new. There’s no need to have any loyalty whatsoever to any conversation thread. In fact, cutting it off for no reason at all (even when it’s going well) and then jumping back into it later is a great way to keep the conversation exciting and unpredictable (more on this another time).

9. Your Own Boredom Will Help You

If you’re making a ton of approaches (as you should be), and after having dozens or hundreds of similar conversations every night, you might want to pull out your hair when the next Keio student asks you “Why are you in Japan?” It’s not that you have run out of things to say – you just simply don’t care about this particular conversation. You know it’s a legitimate question but just can’t be bothered to answer it yet another time.

So make something up.

“To eat tuna.”

“To sell cardboard boxes”


Anything. Providing an atypical answer to her question spikes her interest and shoots a little notification to her brain – “This one’s different! Investigate further!”

Write down the 5 most common questions you’re asked and think of an exciting or different way to answer each.

10. Utilize Non-Aristotlean Logic

This is basically a fancy way of saying “nonsense” and it’s pretty related to #8. If I ever sensed the conversation veering into boring repetitive-land, I’d simply throw out a bunch of random nonsense and let myself figure out a meaning (or not) after the fact.


Girl: Oh, I see. Do you like Japan?

Guy: Pineapple starfish Marxists.

Girl: What?

Guy: Anyway, the third quadrant to the left of the sun… Here come to this conbini for a Chu-hi.


Some people might think this above example is hyperbole or extreme, but what if I told you it’s totally normal. Hijacking the frame and totally derailing the conversation with nonsense (either explained or not) is an extremely effective way to retake control of the conversation, move things in a new and refreshing direction, and keep things on your agenda.

Well that’s a lot of information up there on how to never run out of things to say. Time to go out any apply it! Pick one or two, focus on them for a few sessions until they really stick. Let me know in the comments below what helps you talking forever!


See you next time


3 thoughts on “How to Never Run Out of Things to Say with Girls

    1. Glad you’re enjoying the content! Now that I’m back in Japan from my Euro trip, I’ll be back to updating the site more regularly so check back

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