How to Start a Conversation With a Boy

Compliment him., Comment on the weather., Ask for the time., Compliment him on his pet., Ask if you can sit next to him., Ask for help., Ask a question about class or work., Ask for his opinion., Offer him a piece of gum.

9 Steps 5 min read Medium

Step-by-Step Guide

  1. Step 1: Compliment him.

    So it turns out that guys like to be complimented just as much as girls do.

    Give him the warm and fuzzies by complimenting him on his hair, his clothes, his accent
    - whatever makes him stand out.

    Once he says thanks (which he should) make sure to follow up with another question.

    If you compliment him on his shoes, ask him where he got them.

    If you tell him you love his accent, ask him where it's from.

    Keep it flowing.

    Make sure that your compliment is sincere.

    Don't make it too extravagant, or you will come across as being fake or sarcastic.
  2. Step 2: Comment on the weather.

    You can't go wrong with a harmless observation about the weather, or some other matter-of-fact subject.

    Make a comment about how sunny/windy/rainy it is.

    This gives you a safe topic to break the ice with.

    Once he has responded you can move on to more engaging topics.

    Try to be cheerful rather than complaining, even if it's pouring rain.

    Guys are drawn to positive, smiling girls.

    Turn the situation to your advantage.

    If it's hot, offer him a cooling drink of water.

    If it's raining, offer to let him share your umbrella. , If you're trying to be subtle about starting a conversation, try asking him for the time.

    He'll be happy to oblige.

    Once he gives you the time, thank him gracefully and flash him your most winning smile.

    If he has a nice watch, compliment him on it and ask him where he got it.

    Make to sure to keep your cell phone (which tells the time) out of sight if you're playing this move, otherwise the game is up. , If you bump into a boy while he's walking his dog, then you're in luck.

    Pets are the perfect conversation starter.

    First, you should compliment him on what a great dog he has, then ask if you can pet it.

    Once you and the dog have made friends, you can proceed to ask as many questions about him as you like.

    Winning.

    Ask what the dog's name is, what breed he is, how old he is, and if he knows any tricks
    - the guy should answer questions about his beloved pet enthusiastically.

    While running into a guy with a dog seems to be the most likely scenario, if you happen to see him with a snake or a tarantula you definitely won't be short of conversation material.

    You may not be so eager to pet those critters, however. , Whether you're in class, in the library or on the bus, asking a guy if you can sit next to him is the perfect way to start a conversation.

    Once he says yes, show your appreciation with a killer smile.

    He won't be able to resist striking up a conversation.

    So simple, yet it works like a charm. , Guys can't resist a damsel in distress, so asking for help is a good way to get the ball rolling on a conversation.

    Ask him to help you carry some heavy bags, to open a door when you've got your hands full, or to get something off a shelf you can't reach.

    Thank him sweetly before segueing smoothly onto another topic.

    Another variation on asking a guy for help is to ask him for directions.

    If you're lucky he might even accompany you to your destination.

    Take advantage of the situation.

    If you're at a sports game, ask him about the score, or to explain a ruling.

    If you're at the library, ask if you can borrow a pen or some paper. , Finding some common ground can really help to break the ice in a conversation.

    Ask him thoughtful questions about work or class to get the conversation flowing.

    If you take a class together, ask him what he thinks of it, whether he likes the teacher, or if he's interested in whatever you're studying right now.

    Say something like "Have you seen the essay topics for next semester? Do you know which topic you're going to write on?" If you work together, ask him whether he enjoys working there, if he likes the boss or if he knows next week's schedule. , Asking for a guy's opinion will help to break the ice and show him that you're interested in hearing what he has to say.

    If you can get him started on a topic that he enjoys, then you're on to a winner! If you see a guy reading a book or magazine article, ask him what it's about and what he thinks of it.

    If you're familiar with the author, you can ask him how the book compares to the author's other works.

    This is a great conversation starter as you'll be talking about something you already know he's interested in.

    If a song you like comes on the radio or you're lucky enough to be listening to live music, ask the guy what he thinks of the song or band.

    From there, you can ease into a conversation about his favorite music.

    If you're at a cafe or diner, ask him what his favorite item on the menu is and why.

    If you're feeling brave, you could even offer to buy it for him! , Or a mint.

    Or a candy.

    Just a small, kind gesture like this can be enough to get a conversation flowing.
  3. Step 3: Ask for the time.

  4. Step 4: Compliment him on his pet.

  5. Step 5: Ask if you can sit next to him.

  6. Step 6: Ask for help.

  7. Step 7: Ask a question about class or work.

  8. Step 8: Ask for his opinion.

  9. Step 9: Offer him a piece of gum.

Detailed Guide

So it turns out that guys like to be complimented just as much as girls do.

Give him the warm and fuzzies by complimenting him on his hair, his clothes, his accent
- whatever makes him stand out.

Once he says thanks (which he should) make sure to follow up with another question.

If you compliment him on his shoes, ask him where he got them.

If you tell him you love his accent, ask him where it's from.

Keep it flowing.

Make sure that your compliment is sincere.

Don't make it too extravagant, or you will come across as being fake or sarcastic.

You can't go wrong with a harmless observation about the weather, or some other matter-of-fact subject.

Make a comment about how sunny/windy/rainy it is.

This gives you a safe topic to break the ice with.

Once he has responded you can move on to more engaging topics.

Try to be cheerful rather than complaining, even if it's pouring rain.

Guys are drawn to positive, smiling girls.

Turn the situation to your advantage.

If it's hot, offer him a cooling drink of water.

If it's raining, offer to let him share your umbrella. , If you're trying to be subtle about starting a conversation, try asking him for the time.

He'll be happy to oblige.

Once he gives you the time, thank him gracefully and flash him your most winning smile.

If he has a nice watch, compliment him on it and ask him where he got it.

Make to sure to keep your cell phone (which tells the time) out of sight if you're playing this move, otherwise the game is up. , If you bump into a boy while he's walking his dog, then you're in luck.

Pets are the perfect conversation starter.

First, you should compliment him on what a great dog he has, then ask if you can pet it.

Once you and the dog have made friends, you can proceed to ask as many questions about him as you like.

Winning.

Ask what the dog's name is, what breed he is, how old he is, and if he knows any tricks
- the guy should answer questions about his beloved pet enthusiastically.

While running into a guy with a dog seems to be the most likely scenario, if you happen to see him with a snake or a tarantula you definitely won't be short of conversation material.

You may not be so eager to pet those critters, however. , Whether you're in class, in the library or on the bus, asking a guy if you can sit next to him is the perfect way to start a conversation.

Once he says yes, show your appreciation with a killer smile.

He won't be able to resist striking up a conversation.

So simple, yet it works like a charm. , Guys can't resist a damsel in distress, so asking for help is a good way to get the ball rolling on a conversation.

Ask him to help you carry some heavy bags, to open a door when you've got your hands full, or to get something off a shelf you can't reach.

Thank him sweetly before segueing smoothly onto another topic.

Another variation on asking a guy for help is to ask him for directions.

If you're lucky he might even accompany you to your destination.

Take advantage of the situation.

If you're at a sports game, ask him about the score, or to explain a ruling.

If you're at the library, ask if you can borrow a pen or some paper. , Finding some common ground can really help to break the ice in a conversation.

Ask him thoughtful questions about work or class to get the conversation flowing.

If you take a class together, ask him what he thinks of it, whether he likes the teacher, or if he's interested in whatever you're studying right now.

Say something like "Have you seen the essay topics for next semester? Do you know which topic you're going to write on?" If you work together, ask him whether he enjoys working there, if he likes the boss or if he knows next week's schedule. , Asking for a guy's opinion will help to break the ice and show him that you're interested in hearing what he has to say.

If you can get him started on a topic that he enjoys, then you're on to a winner! If you see a guy reading a book or magazine article, ask him what it's about and what he thinks of it.

If you're familiar with the author, you can ask him how the book compares to the author's other works.

This is a great conversation starter as you'll be talking about something you already know he's interested in.

If a song you like comes on the radio or you're lucky enough to be listening to live music, ask the guy what he thinks of the song or band.

From there, you can ease into a conversation about his favorite music.

If you're at a cafe or diner, ask him what his favorite item on the menu is and why.

If you're feeling brave, you could even offer to buy it for him! , Or a mint.

Or a candy.

Just a small, kind gesture like this can be enough to get a conversation flowing.

About the Author

J

Jacqueline Reed

With a background in lifestyle and practical guides, Jacqueline Reed brings 8 years of hands-on experience to every article. Jacqueline believes in making complex topics accessible to everyone.

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