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What To Say To Start A Conversation With A Girl With Ease

A guy with a skateboard starting a conversation with a girl

It’ll be no great surprise to learn, if you want to get to know a woman, you’ll need to talk to her. Having a conversation with someone is how we determine if we’re compatible, what we have in common and if we like each other. But more often than not, we don’t know the person we want to talk to. So how do you start a conversation with a girl, possibly someone you don’t even know?

What to say to start a conversation with a girl you really like

Whether you've seen some woman at the grocery store, yoga or any of the other best spots for meeting girls, you're going to have to start a conversation. For many guys, not knowing the woman first makes them feel awkward. You want to talk to her because you like her and would like to date her. And this only piles the pressure on more, making you feel even more awkward.

Put that pressure together and I guarantee you’re going to go over and say the wrong thing. But how are you supposed to know the right thing to say? How can you tell if she wants to talk to you? The good news is we’re here to help you out.

So let’s take a look at what to say to start a conversation with a girl.

1) Make sure it’s a conversation

One of the biggest mistakes you guys make is going up to a woman and just asking her out (this is something even a lot of the top dating advice books for guys miss). We’ve all been there and all done it. “Hi – you want to go out sometime?” More than likely she’s going to say no, just to get rid of you. This is because she doesn’t know if she wants to go on a date with you. She doesn’t know anything about you.

So when you first go over to a woman, it’s important to remember your objective. You’re not going over there to get a date or ask her out, you’re going for a conversation. Setting it up like this in your mind is a crucial starting point.

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2) How should I start a conversation with a girl? Just talk

If you search online, “how should I start a conversation with a girl?” you’ll likely get back mostly one-sided results. Almost all of these say you should go up to a girl, smile and say “hello”. This might be the most polite way to do it, but it won’t be the most successful.

So for example, you want to start a conversation with a girl in a coffee shop. "Hello," is what a stranger says when they want something from you. As in, “Hello, can I talk to you about…” or “Hello, would you like to donate…” So when you go up to her and say “hello”, sadly, she’ll be suspicious. This means the best thing to do is just talk.

So if you’re both standing around somewhere, waiting in line at the store or waiting to be served at a bar (even if you are using one of the hookup apps that actually work), just dive in. Make a comment about your immediate surroundings, the new drink menu, the number of cashiers they have or something that just happened. If she wants to talk, she’ll add to the conversation. If not, you won’t have to stand around too long afterwards.

Couple drinking and talking

3) Have the right conversational mindset

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 a 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 to 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 an 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.

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Mindset 3: Listening Actively 

One of the common pitfalls of 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 girlfriends. 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 empathize 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 in 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?

Young man trying to start a conversation with a girl

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 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 tonalities and pace to get more emotion across in your conversations. Writing and keeping a journal can help with this skill set.

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.

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4) Join a conversation in process

The most natural way to know what to say to start a conversation with a girl is to listen to what is being said. For example, if you’re at a party and a woman you like is talking to a couple of other people and you know one of them, go over there. Stand in the circle, make eye contact with her and the other people talking, and listen to what’s being said.

At some point, your own thoughts and opinions will be roused. You might want to talk about deep topics to make her interested. Now you can join the conversation, addressing your points to the group and then directly to her. If she’s enjoying talking to you, you can keep the conversation going until it becomes one-on-one as the others drift away.

5) Talk about something neutral – but interesting

When said like that, it sounds easy. You go over, you start telling her about something you read online or saw on TV. But while this is neutral – it’s not interesting. When you want to get to know someone, you can’t just talk about the weather. It needs to be something you’re both interested in. No one likes to be talked at and she’ll want to be engaged. You need to come up with something interesting to talk about with the girl you like.

But if you’re wondering how do you start a conversation with a girl based on shared interests, the best thing to do is go to a place associated with interests. For example, if you’re at an art gallery and you see an attractive woman there, chances are she’s into art. The same goes for hiking trails, gardening store and volunteer projects. These all lead to natural conversations.

It may sound cliché, but the one thing most people have in common is a love of food. Ask her if she’s tried a new restaurant in the area, or what her favorite food nation is. This can lead naturally on to the ‘ask out’ if things go well.

Couple laughing at the beginning of a conversation

6) Use conversation starters

These used to be called ‘pick up lines’, little comments you could use on any woman to start a conversation. But these only work if they’re novel. Otherwise, all you’ll get is an eye roll. Today, if you’re asking, “how should I start a conversation with a girl?” you’re asking about conversation structure. And this is something much different.

To start off, you need your opener. This might be, “Don’t I know you from somewhere?”; “Aren’t you from Chicago?” “Didn’t I see you last week at the art museum?” These are your classic openers.

She might know it’s an opener. In fact, most older women will. But if she likes how you look, she’ll go along. The key is to phrase the question as a negative. These questions take more concentration to answer and are often more engaging.

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In this case, you’re looking for ambiguous answers such as, “I don’t know”, “Maybe”, “Could be.” Although these are vague in this context they’re welcoming. These answers signal, she’s still thinking and she wants you to keep talking.

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.

7) Introduce yourself

Now you’ve made eye contact and caught her attention, you’ll want to show her who you are. You do this by following up the conversation starter. You could say, “Because I’m from Chicago”, “I go to the art museum, quite often.” Now she’s learning a little bit about you, your interests and where you’re from. This is an indirect introduction and something you need to master if you want to know how do you start a conversation with a girl.

You’re going to wait on giving her your name, occupation and any other details until just the right moment, which is coming up soon. First of all, you just want to let her look at you and decide if she likes you before you start acting like you like her.

8) Ask her a question

In the age-old dilemma of, how do you start a conversation with a girl? This is usually the answer, even if you're not a good conversationalist. Ask her a question. But remember, you want to keep it light and sociable. Don’t ask her about her age, if she’s single, if she has kids or where she works. This is just statistical data. She doesn’t want to be quizzed.

Instead ask her about her opinions in a fun way, which will make her realize you’re a gentleman. You can ask her, “what’s your favorite book?”, “If you won the lottery tomorrow, what would be the first thing you’d buy?” or “What country would you most like to visit?”

By asking questions, and looking into her eyes when she answers, you’ll learn more about her. And you’ll create a bonding experience too.

I used to think that simple questions sounded stupid and it’s ‘impractical’ to ask a girl 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 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 examples 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.

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9) If you're bold you can try cold reading her

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 bread and butter 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 colors..."

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 to 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 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 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 skill set 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 look like they work in a creative line or look 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 losses to making cold reads.

You can also make statements about your day-to-day life. Instead of worrying about 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 themselves. It can inspire someone to ask more questions about you. This way, it's a two-sided conversation.

10) Compliment her

We talk a lot in our articles about how to compliment a woman. But the question here is, “How should I start a conversation with a girl?” and surprisingly, the answer is with a compliment. But this is a compliment with a difference. You’re the compliment.

A couple of points above, I mentioned introducing yourself without giving her your name. But now is the time to do so.

If you think about traditional compliments, what do they do? They flatter. You tell her you like her eyes, her smile, the way she dresses etc. But the biggest compliment you can give her is to tell her you find her really interesting and high worth. You could just say this in so many words, but that usually comes off as insincere. But if you show her you’re really interested in her, you can do just that.

As she’s finishing answering a question you’ve asked, you’re going to take a breath and show her you’re pausing. Let her see in your face how pleasantly surprised you are by the feelings she’s stirring inside you. Then you introduce yourself and ask her name too. “By the way, I’m Mark. Hi. What’s your name?”

This is a really important point of flirtation. It says, you just came here for a conversation but have been sideswiped to find out she’s a really interesting person. The message goes – only just now have you realized how attractive she is.

This may sound a little fake, but if you genuinely go into every conversation just to chat, it’s not. And this is the importance of knowing how to start a conversation with a woman. You shouldn’t just be talking to women because you want to ask them out. In fact, the most men who date a lot don’t do this.

Getting used to starting conversations means you’ll become better and better at it. And probably, it’ll be the ones that start off as just conversations, which end up surprising you the most.

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How to Keep a Conversation Going With A Girl

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 the 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 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-deprecating. 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.


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