Dating and Relationships
You see her sitting across the table of Starbuck having a quiet cup of coffee. She’s dressed casually, in a purple-pink dotted dress that spells classy. She’s attractive. She’s also alone. The hundreds of possibilities run through your head. You want to start a conversation with her and potentially get her number. However, you freeze and you don’t know what to say, much less how to say it. How many of us experience similar situations like this?
Starting a conversation with a girl, or any stranger is a skillset that can be learnt.
How to Start a Conversation with a Girl – Conversational Mindsets
Firstly, you need to understand that there are good conversational mindsets that can make or break a conversation.
This can be done by adopting simple conversational mindsets such as using effective language, learning the art of making statements, creating endless conversation threads by actively listening and understanding the mechanics of how to connect with someone.
Mindset 1: Lower The Bar For a Conversation
I’m notorious for being too witty and lost in abstract arguments in my head. It has single handedly submarined a lot of social, romantic and business opportunities. In addition to that, just relying on pure wit or intellect is actually a horrible way to communicate in relationships.
It’s a cultural narrative from movies you watch growing up where the actors and actresses often come up with witty lines and the ‘perfect moment’. In reality, is far from the truth. When getting to know someone new, it is going to be a little awkward at first.
The first step to starting a conversation with a stranger and never running out of words is to lower the bar for conversation.
Mindset 2: Statements Versus Questions
Have you ever had someone who you just got to know ask you repetitive questions? I bet you have. It also felt irritating. Girls feel the same way as well. When you go interview mode on her, you’re making the conversational flow one sided.
Instead of going down the route of interviewing her and asking questions. When you make statements, you’re giving your own input and giving her a window to respond to that statement.
The trick here isn’t to just stick to statements. It’s to mix in statements and questions. In Asian culture, if you were just to stick to statements, most girls will not know how to respond. From my experience, they’re just too used to guys asking questions all the time, and haven’t built any social skills to share themselves.
It’s a much better conversational habit as compared to asking questions and waiting for her reply. Of course, if you were to make statements, questions and she just doesn’t respond, it means that she’s not ready to talk and isn’t receptive.
Don’t take it personally and move on.
Statements offer more ‘value’ and opportunity for her to get continue to a conversation than questions. When you’re just going off on questions with a girl, you don’t express your identity, and you don’t really put her in a position to express hers. She’s got to invest in the conversation for the interaction to go well.
Cold reading is a skillset that you can use to make statements. Other simple ones include making observations about the environment or something that catches your eye. It’s possible to turn every question into a statement. For example, instead of asking what she does for a job, why not make a statement that she looks like she works in a creative line or looks like a teacher and etc.
If you get it wrong, she’ll correct you. If you get it right, she’ll be quite surprised at how intuitive you are. There are no loses to making guesses.
You can also make statements about your day to day life. Instead of worrying what to ask her next, you can just go off randomly on your day or events that interest you: ‘I almost got hit by a car this morning’. ‘I hate my boss, he just made me do two times the work today’.
It’s better to be random and interesting than to be predictable. However, don’t be too random, as it won’t work in a Asian/ Singaporean setting.
Statements done right can inspire her to find out more about your. You can now dictate the interaction. She’s the one asking questions, and she’s the one sub-communicating that she’s interested in finding out more about you.
Caveat: I’d like to add that questions are alright in the Singaporean setting, most girls here aren’t really equipped with the social skills to lead the interaction, you’ll be required to do a little bit of babysitting.
Mindset 3: Listening Actively
One of the common pitfalls of learning social skills is to only talk about yourself and only showing interest in the topics that you yourself are interested in.
Just recently, I went out with one of my girl friends. She had relationship woes. For three hours straight, she went on was how shit of their ex-boyfriend treated her. This spanned the whole of three fucking hours. Whilst I’m perfectly cool with lending her a listening ear, it just got downright irritating after awhile. At the end of the hang out session, I didn’t exactly feel appreciated for lending a listening ear.
Here’s a trick. If you want to feel better about yourself it’s better to step outside of yourself and empathize with someone else’s problems. Instead of having a self-defeating loop in your mind, merely focused on your own problems, your own trouble or your own pain. It helps, try it.
If you’re genuinely interested in the world of others. It will lead you to a lot more conversational opportunities than just sticking to your own topics of conversation.
Take a good listen to people around you. Everyone’s attempting to jam their point of view down everyone else’s throat. No one’s truly listening. Communication at the end of the day is a two-way thing. Yes, you get to share your story, once they are done listening to yours, do make a point to listen to their story. Part of being interesting is being genuinely interested remember?
Mindset 4: Use Effective Language
Using effective language means using the shortest number of words possible to in conversation to get your point across. You would rather have 5 minutes of awesome conversation as opposed to 15 minutes of beating around the bush. You will come off as more well spoken and charismatic.
This means removing ‘ahh’ ‘you know’ and ‘erhms’ and other filters when you’re conversing.
This doesn’t mean you speak like a robot either. You can use different tonality and pace to get more emotion across in your conversations. Writing and keeping a journal can help with this skillset.
When there’s nothing to say, don’t feel like a need that you have to say something. That’s part of being grounded in your social interactions. There’s no need to fill every silent gap with something to say. People who can’t help but ramble on to ‘keep the peace’ is displaying a form of anxious attachment.
When in doubt, ask yourself, ask yourself, are you saying something because you’re afraid of the silence or the slight confrontation? If the answer is Yes, then it’s OKAY to keep to yourself. Remember, you don’t need permission to speak to anyone, or not speak to anyone.
How to Start a Conversation out of Nothing
Skillset 1: Asking Innocuous Questions
I used to think that simple questions sounded stupid and it’s ‘impractical’ to ask someone on such questions. However, I realized innocuous questions are a mere social tool and conversational starter to get some social juices going when talking to strangers.
No one goes deep into their life story in the first few minutes of getting someone new. And no one expects a life story within the first few minutes either.
Some example of innocuous questions:
- “What are you up to here?”
- “How’s your day?”
You’ll be surprised how far these innocuous questions can help is starting a conversation with a beautiful stranger.
Skillset 2: Making Simple Observations
Secondly, you can also start a conversation with a stranger by making simple observations. You can get creative with this. It can be something in the current environment you’re in, it can be the cute dress that she’s wearing, or the cute blue toenails she has spent hours on. It can be the weather. It can be the fake tan she has on. (I’m kidding)
- “Wow, the weather’s pretty hot today.”
- ‘Those are nice blue toenails you have on, they are really cute.’
Just like asking innocuous questions, think of it as a conversational starter. Once you get small talks like that going, you can follow these observations up with a question, or a cold read.
Skillset 3: The Art of Cold Reading
Cold reading is the art of making an intelligent guess about something about someone. It doesn’t matter if you’re wrong or right. The point of it is to get the conversation going. It’s one of the most effective and a bread and butter of conversational tools that you should include in your daily life if you’re looking to improve your social and communication skills.
Cold reading is done by making harmless neutral assumptions with the people you are talking with.
Examples of Cold Reading:
- “Hi, you seem to be a really artsy person. Did you take an arts subject in school?”
- “You look like you’re a school teacher, you must be a pretty bad one, all the kids must hate you”
The thing about cold reading and guessing is that you never go wrong with it. If you get it wrong, he or she will correct you, and perhaps add onto it. If you’re spot on, she’ll likely to think that you’re quite perceptive and may engage with you in conversation because of that. Just last week I got most of my cold reads right by chance by guessing a girl was half Japanese and was studying at the University of London. She reacted positively and was curious how did I know so much. I followed up by teasing that I stalk her daily on Facebook and Instagram.
Through cold reading, you can keep conversational threads flowing and then relate these threads back to your own life with your own experiences.
I’ve personally used this conversational tool thousands of times to spark new conversations or in the middle of dying conversations threads. It works brilliantly.
How to Keep a Conversation Going with a Girl
One of the most commonly asked questions in dating advice for men is how to keep a conversation going with a girl? How to never run out of words?
In social interactions, you’re going to assume to the burden of taking the lead, to start, to continue and to lead in the conversation. Instead of ending your conversations with one-word answers: Yes or No, try to end it with stories, statements and specifics.
There’s a misconception in conversation that people pay attention to words and phrases. However, it’s meaning that people are more interested in. If you just pay attention to to phrases and words, it may result in an unnatural conversation. It’ll seem as if you’re trying to keep this conversation going and you’re afraid of silences.
The secret to creating endless conversational topics is to get good at improvisation. You can only get better with this skill by learning from stand up comedians. I started off studying George Carlin and Louis CK, however, their style of comedy can be quite dark and self depreciating. That’s not really good for most situations, remember, to attract women, you need to be perceived of a ‘higher status. One of the good comedians to check out is Russell Brand and Russell Peters.
You need to gain an appreciation of language for general and a certain degree of wit.
This is the art of being aware of multiple meanings to a word, phrase or intonation and playing around it. This requires to art of taking note of little nuances, words that she say and playfully adding in a tease here and there.
How to Tell a Story
Ever know someone who went on, and on and on and you can’t help but quietly look away whilst he goes on and on to kind of signal that he’s being too long-winded? Or maybe you know someone who awkwardly tries to fit in a joke in his conversations?
Starting conversations is an important skill. However, learning how to continue them in a dynamic manner is also equally important. Human beings, by nature, are enrapt by stories. People in power, businessmen, priests (erhem), comedians, and politicians all use the art of storytelling to explain, persuade and influence others to their way of thinking.
In the dating advice community, memorizing stories and routines is one of the method. Whilst this might work in the short run, there’s going to come a point of time where you’re going to run out of words. Hence, I advocate understanding the principles of what makes a dynamic conversation and apply them using your own life stories and experiences.
Learning how to tell a story in a structured, and interesting manner will make you a good communicator. Here’s a three-step process that anyone can use.
The set up gives context to the conflict of the story. It’s the general setting, such as the location and brief details of the story. The set up should be as short as possible. But it’s necessary to give the initial context and foundation for the follow-up of the complete story.
If you don’t set up your stories, you’ll come off to others as random in your conversations.
One simple one lined example of the “set up” would be this:
“I was attending my school orientation the other day. Whilst watching the orientation games, there was this girl that tripped and fell. I was an asshole about it and laughed a little.”
It’s descriptive and gives background to the story.
The conflict is the part where you introduce the majority of the story. This should be the part that causes tension and expectancy. The content of the story needs to be captivating and hook others into wanting to know what will happen next. If there isn’t much conflict in the content of your stories, you will get the feeling that you ramble on a lot and others are not paying attention to you.
To continue to story from the set up:
“One of the most attractive girls in the whole of the camp took me by surprise and gave me a smack on my arm. I actually froze up! I froze up and walked away like an idiot! I should have just said something out of my mouth or smacked her back. But I didn’t. I retardedly froze up and walked away.”
“However, I never really felt right, that’s because I didn’t want myself worth to be judged on how many girls date, or anything like that. I also felt I wasn’t experienced enough to coach guys that might be twice my age.”
- The Resolution/ Punchline
The resolution and the punchline are where you insert ‘the moral of the story’, the ‘punchline’ and the ‘joke’ to end off the story, or just closure for a generic story. People who don’t conclude their stories properly will often get blank stares when they’re finished speaking, or people will ask them “Yeah, and…?”
To end off the story with a punchline:
“Lesson learned! Never ever stand beside an attractive woman during orientation games.” (Joke)
“Nonetheless, I’ve decided to give it a shot, as long as I do my research, and stick to my values, and business values, I’m sure it’ll turn out alright.”
These are all true stories by the way.
Learning how to structure your conversations is helpful in sales presentations, networking events, casual conversations and other forms of social interactions. It can make or break an interaction a girl you cold approached that’s expecting you to lead in the conversation.
This is a conversational habit has helped me over the years with strangers, sales and persuading others in business and especially so in my dating life. Connecting with others in a meaningful and dynamic way is part of having emotional depth.
The Art fo Qualification: Empathy and Appreciation
Mark Twain was quoted saying: “really great people make you feel that you, too, can become great.”
When was the last time someone took notice of something about you and appreciated that aspect of you. I feel appreciation is something that’s left out in our culture and conversations. That’s because it requires vulnerability.
The secret desire that everyone desires to be appreciated and to be admired. The art of qualification is the art of appreciating someone of their values or personality. The only way to get good at this is to stepping outside your daily judgments and asking yourself why someone behaves the way they do.
I also don’t mean it in a manner where you compliment someone for the sake of saying. You have to convey your compliments in an authentic manner.
The guy who seems fearless in his entrepreneurial pursuits, selfish with his time, demand and uptight about his schedule, isn’t actually being an asshole. He could be working on a huge project that may help his family financially.
Someone who is extremely financially motivated might not be money minded. He might be doing it because he had a negative experience financially when he was young.
I choose to write about relationships because I essentially care about this area of my life. It’s not because I want to an annoying asshole dishing advice to everyone that bothers to come my way. It must obviously mean something to me.
Writers make choices. So does everyone, with whatever they choose to pursue.
The world is mired in advertising, society, family, friends telling you and everyone else that they aren’t good enough. If you’re able to dig beneath the surface, figure out why people do what they do and appreciate them for that, you’ll stand out from the norm in their lives. It’s only when you find that gold her in, appreciate her for that, that she’ll lit up like a Christmas tree in front of you.
How to Build an Emotional Connection
Society often shames us for expressing what you really feel or think. Hence all of us grow up to hold back our thoughts, desires, and feelings, whether be it consciously or subconsciously. However, as humans being, we all have an emotional need for connection and significance in our relationships.
If you’re going to meet her and merely talk about the weather or gossip on your mutual friends or nerd out about politics, then you aren’t being really vulnerable. If all you know about someone is merely the superficial facts about someone, then you don’t really know someone at all.
The majority of men communicate through information, fact and theories and women connect through emotions. The majority pay attention to the “WHATs” of life: their job, their cat’s name and where they live. They rarely peer into the WHYs.
Conversing with emotions will not only help you connect to women in a deeper manner, but it’ll also help you connect with family, friends and people on a more meaningful level. Deeper friendships and romantic relationships aren’t just built by the number of experiences two people have together, it’s also built on opening up to each other.
No matter how different, everyone in the world has gone through some form of success, failure, hurt, disappointment, anger and lost. If you want to connect with someone emotionally, you got to open yourself up and connect with these universal emotions and experiences. You want to relate to the underlying emotions behind the facts. The facts are mere superficial details of the emotions experienced.
I often tell people that I’m quite a good judge of character and someone else’s motivation. That’s because I pay attention to the undercurrent of what someone is saying, as opposed to the superficial layers of communication. Powerful emotional connection is built upon understanding and relating to each other’s WHYs in life.
You need to pay attention to the motivations behind pursuits and behaviours.
Here’s an example of going into the WHYs:
Her: Wow, what inspired you to be an entrepreneur at such a young age?
Me: I pursue business I want to be financially free because I felt financially suffocated during my teenage years as my family went bankrupt for a period of time.
That is a ‘Why’.
Here’s another way to tell a story in a dynamic way:
I was once a competitor in Brazilain Jiu Jitsu and currently I’m an entrepreneur. The feeling before a Brazilian Jiu Jitsu competition is the same pressure before a giving a business pitch.
They are both some sort of competition in some way. One of them is trying to overcome a physical challenge whilst the other a financial one. The Brazilian Jiu Jitsu competitor is risking failure, success, and embarrassment just like how the entrepreneur is.
Never thought how a Brazilian Jiu Jitsu champion can relate to an entrepreneur uh?
Everybody on this planet shares a handful of universal emotional realities: ambition, shame, alienation, loneliness, achievement, regret, hardship, friendship, love, heartbreak. We’ve all experienced it. The facts change, the feelings are the same.
It’s just how well you’re able to express yours, which will inturn inspire her to share hers. This requires some amount of patience. Some people carry themselves in a superficial manner in order to fit in with society. However, everybody has it somewhere in them. It’s your job to dig it out and connect with that part of her. That’s where the gold is. That’s where the real magic happens.
- Be Aware of Your Own Life Stories and Motivations
The rule of thumb here is to always go first. If you share a vulnerable part of yourself, it’ll inspire her to share about hers. To do that, you have to be firstly aware of your own emotions, motivations, and life story.
- Your passions and favourite things to do
- Your dreams, ambitions, life goals
- Best/worst thing that has happened to you
- Your childhood, family life and upbringing
You can initiate these conversations by a simple cold read: You look like you’re close to your family.
This is where majority of guys fail at this. Men tend to discuss technical know-hows and superficial details rather than be introspective about their own emotions. The majority guys suck at talking about themselves. They think it’s weird in some ways. Girls, on the other hand, are only engaged when they are talking about themselves (or each other). This is why they’re constantly gossiping, creating drama or people watching.
Here is an example:
I always wanted to be a psychologist growing up because I had a lot of problems growing up as a rebellious teenager. I was always angry, apathetic and under performing. I ended up being hooked onto self development due to a horrible break up with my ex-girlfriend. I was addicted to the fact that I could have a control over my dating life and social interactions.
Through years of failure, today, I feel much more in control of my dating life. I took an interest in psychology that partially inspired my entrepreneurial projects.
However, if you talk about how you FEEL about your interests, then you can relate to how she FEELS about her own pursuits. It’s never the external pursuits, it’s the similar underlying expression why you choose to pursue something that you can relate to her with.
Here are some examples:
She studies really hard to get into law school because she was brought up by a single Mum and she wants to be self-reliant and independent. That’s driving her. You can relate to her by saying that you had a distant upbringing with your family and you always had to rely on yourself emotionally to get by.
It’s never about the external pursuits, but it’s about the similar underlying expression of why you choose to pursue your chosen hobbies that you can relate to her with.
When you open up about yourself relate to each other’s emotions and experience., you’ll elicit her to to open up about herself. The more this goes on, the more personal stories become and the deeper the emotions you connect with. The harder it is to talk about it as a subject, the more genuine and attractive it potentially can be. Topics such as childhood, upbringing and family life are often hard for a man to express, especially so in Asian culture.
Here’s a reframe: by being alright with sharing any part of yourself with anyone, you’re truly confident.Emotional connection occurs only through exposing yourself to a certain degree. It cannot be faked.
Confrontation and Appreciation
Lastly, confrontation is necessary to build a deeper emotional connection. Think of it as a parent who sits you down, says something that you don’t want to hear, but know that you should hear. You hate it at first, however, you know they’re doing it because they care for you.
Confrontation can be painful and vulnerable. The majority of people avoid confrontation in the fear of imploding the relationship. Confrontation is something I’m start to get more comfortable with as I grow older. This is especially so with close relationships.
However, it is necessary.
Recently, I confronted two good friends. I was feeling really upset for their unreliability and a host of other issues. I kept it in for months. However, it finally felt inauthentic to be around them without expressing those issues. It didn’t feel like a genuine friendship anymore. It felt like I was holding back my thoughts and desires in fear of losing the relationship.
Confrontation from a dating aspect can be as simple as calling a girl out for being half an hour late into a date to confronting your girlfriend about those weird late night calls to her ex. These events are often painful, but necessary. However, that’s how an authentic relationship is built.
Putting it all Together
Combine this framework with skill sets such as cold reading, making statements over questions, storytelling, improvisation and you’ll find yourself in being able to direct and control the flow of conversation. This is actually easier than it sounds. You probably already different parts of these strategies time to time with your friends. Now, you just got to do it consistently with girls you’re going out with.
When I was 17, and I was the biggest countercultural hippie. I listened to John Lennon, proclaimed that all you need is love and just felt that life was all too short to be worried about you know the practical stuff.
I sat at the playground near my house I was with my ex girlfriend who I was dating at that point in time. I sat and both of us chatted for hours.
I went off about how societal expectations were ridiculous and gave a mini-lecture if the universe existed or not. I told her how amazing was to exist as a tiny speck of the universe. I ranted passionately for a good hour. She listened. She listened well.
I then caught myself rambling and stared into her eyes.
I said: “Were you even listening, did you understand what I just said?”
She said: “No, I don’t, but I just love the way you say it.”
I got annoyed because I wanted her to understand the content of you know, all of that hippie stuff. She didn’t. However, years later, looking back, she probably loved how I expressed it. It was passion and story telling at it’s finest. That was because those stories demonstrated my passion, my authenticity.
Fast forward years later, and I found myself dating this other girl at this bar near my home. That point of time, I had hung out with other pick up artists, read quite a bit on ‘Game’ and all of that self-improvement stuff.
I was also a competitive martial artist at that point of time and was preparing for a Brazilian Jiu Jitsu tournament. I ended ranting off on about how Jiu Jitsu is similar to the game of human chess. I told her Brazilian Jiu Jitsu was akin to facing death. I explained to her that by being submitted in a Brazilian Jiu Jitsu match, it is the equivalent of dying. You’re either choked out, or risk suffering a major limb broken, which will lead you to a huge disability continuing the fight. I then went on about how Brazilian Jiu Jitsu teaches everyone to be humble because getting into a physical altercation in reality always pans out differently.
I went on, and on. Guess what? She loved it. She just stared at me like my ex girlfriend did, mesmerized at how I went on passionately about something I cared about.
Complete different girls, and completely different stories. Nonetheless, the same universal emotions. The facts often get shifted around, however, the feelings are always same.
Should You Memorize Lines?
I never felt right memorizing lines or ‘openers’. It has also never worked well for me. Furthermore, you don’t want to be some robotic guy repeating what somebody wrote on the internet. However, if you’re starting out you can use certain one line jokes or memorize some of own life stories as training wheels.
You want to understand the principles of conversations, and use your own unique life stories and motivations. This will serve you much better in the long run. Not to mention human interaction has many variables that are out of your control, and cannot be completely boxed and quantified like a formula.
Just so you know, I’ve sparked conversations with girls in clubs all over the world with this simple line: “Hi I’m Marcus, I just wanted to say Hi, you look like…”.
I haven’t had a drink splashed on me yet.