How to Start a Conversation with a Girl (Even if You are Shy)

By Marcus Neo | Dating Advice for Men

Jan 02
Couple alone in a restaurant

You see your ideal girl sitting across the table at Starbucks having a quiet cup of coffee. She is dressed casually. She looks kind of intimidating. She’s also attractive. She’s also alone. The hundreds of possibilities run through your head. Or maybe you are at a networking session are you see the hiring manager of your dream job standing beside a booth. You want to try start a new conversation with her. However, you freeze and you don’t know what to say, much less how to say it.

How many of us experienced similar situations like this? The question begets: how do start a conversation with a girl even if you aren’t naturally “extroverted”?

This is a skillset that anyone can learn.

How to Start a Conversation with a Girl – Conversational Mindsets

Firstly, there are good conversational mindsets that can make or break any new conversation.

This can be done by adopting conversational mindsets such as 1) using effective language, 2) learning the art of making statements, 3) creating endless conversation threads by actively listening

Mindset 1: Lower The Bar For a Conversation

The first step to starting a conversation with her and making sure you never run out of words is to lower the bar for conversation.

In my younger days, I was notorious for being too witty or lost in abstract arguments in my head. It single handedly submarined a lot of social, romantic and business opportunities. Only relying on pure wit or intellect is actually a horrible way to start a conversation, much less connect deeper with a woman.

The need for serious or deep talk in the first couple of minutes is a narrative from movies you watched growing up where the actors and actresses often come up with witty lines and the ‘perfect moment’ to start talking to someone new. In reality, this is far from the truth. Starting a new conversation is always a little awkward at first. Just keep it simple.

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. Guess what, people feel the same way as well. Let’s not treat new conversations like an interview, shall we?

In general, statements offer more ‘social value’ and opportunity for the other party to get a conversation going.

Instead of going down the usual route of interviewing someone and asking questions… you can make statements. This way you’re giving your input and giving them a window to respond to that statement.

The trick here isn’t to just stick to statements. It is to mix in statements and questions. However, if you were just to stick to statements, most people will not know how to respond. From my experience, they’re just too used to people asking questions all the time and haven’t built any social skills to talk about themselves.

Making statements is a better conversational habit as compared to asking questions and waiting for their reply. Of course, if you were to make both statements and ask questions and they won’t respond, it means that they are not ready to talk to someone new.

There’s no need to take it personally and move on.

If you’re sticking to questions, you don’t get to express your identity and you don’t really grease the wheels to help her express herself. She gets to take part minimally in the conversation.

Mindset 3: Listening Actively 

One of the common pitfalls starting a conversation is to only talk about yourself and only showing interest in topics that you are interested in.

One time, 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. That spanned the entirety of three damned hours. Whilst I’m perfectly cool with lending a listening ear, it just got downright exasperating and I felt like killing myself at the end of the session.

One a side note: if you want to feel better about yourself. It’s recommended to step outside of yourself and empathise with someone else’s problems. This is much better than ruminating through a self-defeating loop in your mind, obsessed over your own problems, trouble and pain. It helps, try it.

If you’re genuinely interested learning about others, it’ll lead you to a lot more conversational opportunities.

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.

Conversations at the end of the day are 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?

Trying to get a girl's attention

Mindset 4: Use Effective Language 

One principle of being a great communicator is by using effective language. This means using the shortest number of words possible to in conversation to get your point across. You’ll rather have five minutes of succinct  conversation as opposed to fifteen minutes of beating around the bush. This way, you’ll also come off as more well spoken and charismatic.

This means removing ‘ahh’ ‘you know’ and ‘erhms’ and other filters when 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. In psychology, it’s said that people who can’t help but ramble on to ‘keep the peace’ may be 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 with a Girl

Skillset 1: Asking Innocuous Questions

I used to think that simple questions sounded stupid and it’s ‘impractical’ to ask a girl such questions. However, I realised innocuous questions are a mere social tool and conversational starter to get some social juices going when talking to strangers.

No girl is going to go 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 an interesting stranger.

Skillset 2: Making Simple Observations

Secondly, you can also start a conversation with her 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 nicely tailored suit that he’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. (read: I’m kidding)

  • “Wow, the weather’s pretty hot today.”
  • ‘Those are nice blue toenails you have on, they are really cute.’

Through 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 cold reading is to get a new conversation started. It’s one of the most effective and a bread and butter of conversational tools that you should include in your arsenal.

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… with that crazy hair you must be a pretty bad one, all the kids must stare at those crazy colours…”

The thing about cold reading and guessing is that you’ll never go wrong with it. If you get it wrong, she will correct you, and perhaps add onto it. If you are spot on, they’ll likely to think that you’re quite perceptive and may engage with you in conversation because of that. One time I got most of my cold reads right by chance by guessing a girl was half Japanese and studied at 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 cold reading thousands of times to spark new conversations or in the middle of dying conversations threads. It works every time.

Cold reading is a skillset that you can use to make statements. Even simple ones that 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 someone does for a job, why not make a statement that they looks like they work in creative line or looks like a teacher and etc.

If you get it wrong, they’ll correct you. If you get it right, they’ll be quite surprised at how intuitive you are. There are no loses to making cold reads.

You can also make statements about your day to day life. Instead of worrying what to ask next, you can just go off randomly on your day or events that interest you: ‘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.

Statements done right can inspire someone to find out more about yourself. It can inspire someone to ask more questions about you. This way, it’s a two sided conversation.

Caveat: I’d like to add that questions are alright in an Asian setting, in some Asian cultures, people in general aren’t really conditioned to lead a social interaction, you’ll be required to do a little bit of babysitting by mixing questions with statements.

How to Keep a Conversation Going

Now that you have started a conversation, how do you keep a conversation going with her and never run out of words? It’s best to assume to the burden of taking the lead to start, to continue and to lead conversation. Instead of ending your conversations with one-word answers: Yes or No, try to end it with stories, statements, emotion and specifics.

  • The Art of Improvisation

There’s a misconception that people pay attention to words and phrases. However, it’s the meaning of the conversation that people are more interested in. If you just pay attention to to phrases and words, it’ll 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 in attempting to better my chances with women, however, their style of comedy can be quite dark and self depreciating. That’s not really good for romantic situations. There are other good comedians such as Russell Brand and Russell Peters.

The best way to get good at improvisation is to gain an appreciation of language. Improvisation is impertinently important in learning to tease and build a sense of camaraderie. Old friends tease each other. Lovers tease each other. You can break the ice by being good at improv and teasing.

How to Talk to Girls - Start a Conversation and Connection 03

How to Ask For Her Number

If you strike up a conversation with a woman and there’s a good feeling between both of you, then you can ask for her contact details. I generally find interactions that last lesser than 5 minutes don’t go anywhere. However here’s the thing. If she likes you and assuming you’re generally a friendly non threatening looking individual. Your conversation is going to naturally last more than 5 minutes.

Once you feel like you’ve gone from stranger to acquaintances, you should ask her out for a coffee right there and then. I always do that. You can also frame the way you ask her out.

“You’re nice to talk to, you seem like an interesting person, let’s grab coffee some day.” 

Only when she agrees, then ask for her number. There’s no perfect line to ask for her number. Just say:

“Let’s keep in touch and let’s exchange contacts.”

I say this all the time, the words are superficial, it’s the intention underneath it that counts. If she says no, then it’s alright as well. Just wish her well and move on.

About the Author

Enjoys writing about dating, relationship, business, and psychology. Introvert yet extrovert. Likes martial arts and music, but never got around to the latter.

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