Sometimes simple things become very complicated.  Conversation is one of the basic ingredients of civility, and we take it for granted,  but the moment a man has to start a conversation with a woman he likes, all bets are off. 

How to start a conversation with a girl

Despite the advice thousands of pundits offer on how to start a conversation with a woman-pickup- lines, most men still find it hard to do.

25 1-on-1 Conversation Starters

  1. Can you describe yourself in three words?
  2. What did you do on your last vacation?
  3. If you had to open your dream business, what would that be?
  4. If you could do anything with a guarantee you will not get caught, what would you do?
  5. Are you a morning person or an evening person?
  6. Do you enjoy speaking before large crowds of people?
  7. If you could donate a million dollars to a charity, choose one?
  8. Are you a summer or a winter person?
  9. How much time do you spend online?
  10. If you could select a new name for yourself, what would you be called?
  11. What is your very first memory, when you were very young?
  12. Do you prefer physical books or e-books?
  13. If you had to take only one book with you on an around the world boat cruise, it will be?
  14. Do you play any instruments?
  15. Who is your favorite singer of all time?
  16. Do you participate in sports?
  17. What is the worst meal you ever had in a restaurant?
  18. What was the worst service you ever had in a restaurant?
  19. What is your absolute favorite meal of all times?
  20. What is your favorite snack?
  21. Do you enjoy wine?
  22. What is the most exotic place you still want to travel to?
  23. If you were to be allowed to achieve only one goal in your life, it would be?
  24. Do you like spicy foods?
  25. If you could call any person in the world right now, and speak to them for one hour, who would you call?

25 Online Conversation Starters

  1. What is your favorite song?
  2. What is the funniest picture you have on your phone?
  3. What is the best thing about being a woman?
  4. If you had to choose one character from the movies to explain to me who you are, who would you choose?
  5. Which celebrity is closest to your ideal looking man?
  6. What event would you like to relive in your life if you could go back?
  7. What’s the most important thing you carry in your purse?
  8. If you look out of the window right now, what do you see?
  9. When did you last laugh until you almost cried?
  10. What is the biggest lie anybody ever told you?
  11. Facebook or Twitter?
  12. Which app do you use most often?
  13. What do you love most about yourself?
  14. Name any movie you have seen more than 5 times?
  15. What type of phone do you have?
  16. What is your favorite ice cream topping?
  17. Do you prefer to text, message or call?
  18. Do you ever leave voice messages?
  19. Best way to travel, plane, car or train?
  20. Best invention of the last 50 years?
  21. The most embarrassing piece of clothing you own?
  22. What is your favorite perfume?
  23. Do you like driving really fast?
  24. Do you like spicy food?
  25. What were you doing just before we started talking?

Why is it so difficult?

Debra Fine wrote in The Fine Art of Small Talk (2005) that the things we learned as children often linger on into adulthood.  She listed some well-known and over used adages she said, were partly to blame for some men’s pushback when it comes to understanding how to start a conversation with a girl. These included:

Good things come to those who wait. Don’t ask her now. Tomorrow is another day.
Silence is golden. Don’t talk to her now. She is preoccupied.
Wait to be properly introduced. It is rude to barge in on her.
Don’t talk to strangers. You can’t talk to her if you don’t know her.

Before we can make sense of the advice pundits offer on how to start a conversation with a girl,  we need to break free from these beliefs our parents ingrained in us. 

If we do, it becomes much easier to speak to strangers, and we no longer have to hide behind the brazenly impersonal rituals that guide our interaction in public spaces.  For example,  when we share a space on a train with strangers, certain rules of civility come into play. 

How to start a conversation with a girl

Some polite conversation is not only tolerated, but often required for the sake of sociability and civility. So we talk about the weather for example, but we will never ask intrusive questions. We talk about sports-news and train schedules, but never about intimate issues. 

By doing this, we create a personal safe space around ourselves that insulate us from the world and from other people.  This is how we maintain privacy in crowded areas. This insulation, or dare we call it isolation makes it very difficult to start a real conversation with any woman we are attracted to.

Flirt-Friendly Spaces

Different rules apply when we enter flirt-friendly spaces.  In some social venues we are allowed to break free from the self-imposed isolation that is the cornerstone of civility in crowded public spaces.  In flirt-friendly spaces like bars, clubs or restaurants, different rules apply. 

In these social venues we are allowed and even encouraged to reach out across the ‘divide’ in order to meet others socially and even to flirt a little bit.  At these venues men and women choose to interact socially in order to meet and possibly date each other. In this context we are expected to become a bit more open and informal, and civil aloofness can become a social impairment rather than a form of good grace.

Online Dating

The advent of dating sites, especially free dating sites, is disrupting and transforming modern social life.  Flirt-friendly venues are no longer restricted to geographic spaces only. 

The web is setting us free in many ways and free online dating sites offer a completely new dimension where singles can meet and interact.  One of the main benefits of free online dating, is the creation of designated spaces where our intentions become translucent. On free dating sites, women invite men with certain qualities to contact them.

How to start a conversation with a girl

In these safe, flirt-friendly safe spaces, men are strongly encouraged to start a conversation with a girl, and it all happens in cyberspace, while we steer it from the comfort of our own homes, safely shielded by a computer screen.

Going online, makes it easier for men to hone their conversation skills, to test the best pickup lines and to gradually ease into a dating comfort-zone. 

Selecting the best pickup lines that tasteful and can serve as conversation starters, both online and in person, and often lead to dates and long-term relationships.  Regular engagement and playful banter with women on dating sites makes  it much easier to start a conversation with attractive women in public, flirt-friendly zones.

Rules of Engagement

In flirt-friendly venues, specific rules of engagement define the social norms we have to follow when we want to start a conversation with a girl.  Friendliness is the best way to signal positive intentions, and it’s an essential ingredient when we want to start a conversation with a woman. 

How to start a conversation with a girl

Without it, all bets are off. Unfriendly people have no friends.  In order to befriend a beautiful stranger, we have to be friendly.  We reap friendliness when we sow friendliness. 

1. Friendliness

A smile says it all.  Natural friendliness is displayed with a smile, a real smile – not a say-cheese smile.  When someone smiles sincerely, their whole being lights up.

When someone smiles from the heart, their entire person radiates warmth.  Most people can spot a fake smile from a mile away.  Most people have an intuitive ability, call it a gut instinct, that identifies disingenuous people. 

How to start a conversation with a girl

The goal is to become less absorbed and to focus on others.  If we are less self-absorbed and give our full attention to whomever we are interacting with, our sincerity almost becomes viral and friendliness will be just one of the side-effects that will draw in women. 

In an atmosphere of happiness, smiles and warmth, it is much easier to start a conversation with a girl.

2. Optimism

The second rule of engagement is simple: be positive.  Optimism is another crucial element of charisma.  By simply focusing on what is good and right in any given situation we end up radiating optimism – when we seem hopeful and confident about the future,  good things happen.

Optimism breeds success.  What is the use of trying to start a conversation with a girl if failure is expected? Purposefully taking steps to start a conversation with a girl is essentially an act of optimism. Hang out with positive people and develop an optimistic and joyful approach to life, and watch how attractive women will reciprocate.

Optimism can be feigned, and the more you “fake it until you make it” the more genuinely optimistic you will become. Women have no real way to distinguish between real confidence and feigned confidence before they get to know a man.  Irrespective of our inner struggles and insecurities, it is imperative to present the most confident version of ourselves to the world, especially when our goal is to start a conversation with a girl and allow those conversations to eventually evolve into a dating relationship.

3. Confidence

As we discussed above, confidence is directly related to optimism.  When we think about it, confidence and optimism can even be considered synonyms.    

When someone walks across the street with confidence, it implies a belief that the other side of the road will be reached. If someone confidently jumps over a crevasse, it implies a belief that the other side will be reached.

How to start a conversation with a girl

No one can be confident about anything, without being optimistic.  Optimists have confidence. Pessimists suffer from dread.  No one wants to be around a downer and that is what pessimism is all about. 

Consider this…

Very few men will attempt to start a conversation with a girl if there is no hope that she will reciprocate.  It would be futile.

The whole point of a conversation, the defining characteristic of a conversation, is the fair expectation that the other party will reciprocate, and ‘converse’ with us. Optimism, a faith that the ‘other side will be reached’ is implicit. 

At the end of the day, confidence is based on self-reliance. So the woman in question rebuffs the gentleman’s warm and friendly, and tasteful, conversation starter, no real harm is done. 

Just move on.

Nothing gained, and nothing lost – the rebuff says something about the woman in question and not about the man who approached her.

The rebuff is not an indictment of the man, only of the moment he chose to approach her.  This is part of life, so do not take it personally.  Move on and talk with someone that is in the mood to meet a man.

Emotional Traits

Some emotional traits can go a long way towards establishing a confident version of the self:

  • Calm people often seem to be sure of themselves. 
  • Friendly and easygoing people are widely considered confident simply because they do not seem nervous, anxious or jittery.

Do not move or talk too fast, no jittering about or twitching like a speed freak, and confidence will exude.  Women love confident men.

4. Eye Contact

As it has been said,  “eyes are the window to the soul.” A cliché, maybe – but nevertheless true. Human beings can see into each other’s souls because the eyes have a language of their own, and most women speak it very well.

How to start a conversation with a girl

Beautiful eyes are very often not beautiful for their appearance, but for their kindness, love, humor or silliness.  The point is simple. The fourth rule of engagement, is eye contact.  Friendly and positive eye contact, not rude, staring, cold or creepy eye contact. 

Look at her when speaking to her, and allow the eyes to mirror the soul.  People who talk and laugh with their eyes, are very attractive, because the eyes underwrite what the mouth speaks of.  Allow the eyes to radiate sensitivity.  It is very hard for anyone to rebuff a conversation with someone who makes soulful eye contact.

5. Sincerity

Sincerity exists in the absence of pretense, deceit and hypocrisy.  Most women can spot insincerity from a mile away. Sincerity is one of the most difficult things to feign and get away with. The shortest route to sincerity is open honesty and transparency. Do not hand out compliments just to score some points.  If a compliment is not real, it will do more harm than good.  Do not laugh when it’s not funny,

How to start a conversation with a girl

or show empathy when feeling nothing at all. When we feign any of the emotions we signal, we interrupt and disconnect from those around us.  Be one of those people that mean what they say and say what they mean. 

6. Engagement

Listening well is a critical part of a conversation. People who listen well will draw others to them. If we pretend to be interested just to get our way, we are simply obtuse and we will fail. 

A conversation is a two-way street, not a monologue.  To converse, both participants have to rhythmically talk, and listen.  If no real engagement exists, no conversation takes place.

How to start a conversation with a girl

When we listen with joyful abandon, we are engaged in a conversation rather than just taking part in a conversation. Don’t make the conversation all about you.  Be interested in the other person as well.

Strategies for Conversing

1. Small Talk

Small talk plays a major role in human interaction. It is how we bridge the gap between silence and sharing.  Small talk is all about the weather. It’s all about idle chatter and done right, puts a duty on the other party to respond in kind. 

That is how we engage strangers verbally.  When we are in the company of an attractive girl, small talk creates the opportunity to move on from idle chatter to a real conversation.

How about an introduction. “Hello, I am Carl.” Small talk faithfully follows those who introduce themselves. 

We meet strangers by saying “How’re you doing? What brought you here today?”  The answers we receive will be equally trite, but, a small conversation is underway. 

Like a small fire, a small conversation needs a little bit of air and some pieces of dry wood to become a raging fire.  Ask for directions. Offer her a hand with something she is carrying, or mention a movie or television series. 

Anything to keep going. The purpose of small talk is to find some common ground. Maybe she is also a law student.  Maybe she has tickets to a Broadway show and no one to go with.  Small talk opens the door to share, and as they say, sharing is caring.

2. Sharing

Sharing is the human way to go halves on a conversation. It is a process of give and take and results in a deepening of the level of conversation by gradually shifting away from the impersonal public talking points and moving towards the personal and more intimate. 

How to start a conversation with a girl

Most people, once they relax with someone, enjoy answering personal questions.  The right question at the right time, will more often than not lift the veil of feminine mystery and allow a woman to expose whichever part of her she wants to share.

How to start a conversation with a girl

Sharing breeds more sharing. Once a couple has shared their first personal story, the floodgates very often open up for them to discover mutual friends, shared experiences and common interests. Beginning is the hardest part.

3. Flirtation

Many people think of flirtation as a sexual game played by wanton lovers. Nevertheless, flirtation is a form of communication for men and women who are attracted to one another.  The defining characteristic of the flirtatious communiqué, is its playfulness. 

How to start a conversation with a girl

Flirtation shifts the boundaries of the acceptable towards the personal and somewhat inappropriate. People who enter this space are allowed to be more provocative and can try to engender a more sensual and romantic response from one another without showing their hand completely. 

This is the moment to compliment her on her beautiful eyes, magnificent shoes or illuminating smile.  Flattery now becomes less malignant, and can be employed to further a mutual attraction into something more physical. 

By playfully teasing one another, the couple is allowed to engage in more risqué behavior and more sensual conversation that will take the conversation to a deeper level eventually. By purposefully touching each other “on accident” they can test the waters, as it were.  Now is the time to lock eyes and expose your soul.

Final Thoughts

It was Dale Carnegie who wrote: “Talk to someone about themselves and they’ll listen for hours.” The greatest conversation starters are those that tap into this wisdom. Any man that is really interested in a woman will get the best results by remembering not to make it all about himself.

How to start a conversation with a girl

The old song goes “you’re so vain, you probably think this song is about you.’  The secret is to make it all about her.  When a woman comes to understand that a man is really interested in her opinion and her life,  she will subconsciously become interested in him as well.