How to Ask a Boy out in Middle School

Consider how you feel about dating., Know what your parents think., Talk to your friends about dating in general., Move to the next phase if you think that dating is for you., Find out what this boy is like before assuming that he is date-worthy...

25 Steps 8 min read Advanced

Step-by-Step Guide

  1. Step 1: Consider how you feel about dating.

    There is no magic number or time at which a person is ready for dating.

    It's dependent on who you are, how mature you feel and what your parents think about it too.

    Indeed, it's a combination of factors.

    At this point, don't feel bad if you don't actually feel like dating yet––that's okay to, you can have friends instead of dates too and nobody will think any the worse of you for it.

    Take a little time to better understand your own motivations for having a boyfriend or going out.

    How big a factor is each of the following for you: wanting friendship/companionship and someone to hang out with; wanting to have someone else interested in your well-being and listen to your worries and joys; wanting affection (hugs, touch and nonphysical affection, romance, etc.); wanting to be accepted and cool and not seen as a loner by schoolmates? Which of these are your main motivators? The better you understand your own needs and motives, the better your decisions and choices will be about whether to ask a boy out, and if so, who to ask, and how to do it.

    Taking the time to introspect and understand yourself better is a lifelong process important for adults as well as for middle school students.
  2. Step 2: Know what your parents think.

    If they don't think that dating boys is appropriate right now, they mean it and they have good reasons.

    Listen to them and just find friends instead.

    There's plenty of time for love later.

    If you're parents are cautious but open to the possibility, explain how responsible you'd be if you went on a date, such as meeting curfew times, letting them know where you are going and being reachable by phone at all times. , Ask them what they think about dating and how comfortable they feel about it.

    While you don't need to agree with what they say or think, it can be helpful to gauge their feelings and get ideas to form your own thoughts. , Once you're happy that you're ready to date, try getting to know this boy better. , He might not turn out to be the kind of person you first thought.

    It makes good, common sense to get to know him a little before asking him out.

    Fortunately, there are plenty of ways you can use to get to know this great person somewhat better. , Make it a group thing.

    Get your friends and his friends to mingle at recess, lunch and after school.

    Make it all seem most casual, and just hang about chatting to everyone, including him.

    Make friends with him and his friends.

    It will make him feel closer to you without realizing just yet what your real intentions are.

    This gives you the space to study him close up and kindly. , Have casual conversations with him about school, sport, your uniforms, school rules, anything really that is simple, relevant and easy to chat about.

    Find out what interests him and let him know just a little about what interests you.

    Here are some conversation starters: "Want some gum?" "Hey, do you have any gum?" "Okay, no more projects on cells.

    Mine looked like it came out of a horror movie!" or "Random Question: are you a morning or night person?".

    If you are in different years/grades, ask him what he thinks you'd like next year.

    Don't chew his head off with "me, me, me" talk though.

    Instead, make the aim to learn as much as you can about him.

    He'll ask you enough things in time. , Give him little gifts now and then, such as chocolates.

    But be sure to give them to his and your friends at the same time.

    You're trying to prove you're a generous lassie, not someone focused only on him––that comes shortly.

    For now, show him what a great spirit of generosity you are. , Send a friend request and bond online.

    Send casual messages, jokes, funny pictures and nice sayings.

    Keep it light and friendly and include your other friends initially so that he looks like he's just one among many recipients of your online banter.

    As time goes on, you may grow to feel comfortable just chatting or messaging him. , He doesn't want to know what you're doing every five seconds and he certainly doesn't want to have answer to you about what he's doing every five seconds.

    Instead, just get to know his schedule, work around it with the occasional "hello"

    "how's it going" and "wow, isn't funny how we keep bumping into each other?" moments.

    If you're online, take the chance to now and then send something with a "when I saw this, it made me think of you, 'coz I know you like the LOL cat/etc. pictures". , Do you want him to be your boyfriend? Before you ask him out, be sure he's the one.

    Before you decide that you're in love, know what your own feelings are.

    Make a list of the negatives and positives about him, and then decide. , At least have inkling that this guy has grown fond of you and is somewhat into you.

    Signs include him breaking the touch barrier, lingering gazes, fond nicknames, making excuses to be near you, texting or messaging you a lot, blowing you kisses and generally being sweet to you.

    In some cases, he might be a little more brash and teasing toward you, because he feels comfortable around you.

    If you've gotten the impression that he's keen, it might be time.

    Ask him when you feel right and comfortable! , If so, flirt a little, make eye contact more often and pass a few sweet notes to him in class.

    Make it clear that you're keen on him. , He's yours for the taking if you've noted the signs correctly and feel you know him well enough by now.

    Rehearse asking.

    If it helps you to gain confidence, practice beforehand.

    First, write down what you want to say.

    Then, practice in the mirror.

    Look at your body language and facial expressions.

    Practice until you feel confident. , This is especially important at the middle school and junior school levels.

    This isn't about determining your love match for life; it's about gaining a fun and carefree romantic friendship and the main thing is that you both feel comfortable with one another.

    Say something like, "Want to go for a slurpee over lunch break?".

    This is perfect.

    Make sure his lunches are free first.

    Or, casually ask "So do you have band/yearbook/practice, etc. today? Mind if I come too".

    Or, "Hey, would you like to come with me to the movies/park/skate rink, etc. this weekend?" If asking him out over text message, say something like: "My friends think we should get married.

    Spring wedding sound good?" Expect a "lol" as a response.

    Then after he responds, say something like, "Yeah, but I really do like you." Do try to use full words as often as possible; text messages can look really stupid if you use text language (u for you, r for are). , Realize that he may need time to process your request to get together, hang out or go on a date, and that's fine.

    Let him know it's fine and that he can get back to you.

    If he says no, that's all right.

    He's probably embarrassed, or he hasn't made up his mind.

    Be understanding, and don't become defensive or act hurt.

    Never stall or make excuses.

    But at least he knows you like him and he might start looking at you in a different way.

    If he says yes, say "great" and start planning your date, make sure you pay, unless he insists.

    Some guys love it when the girl pays, it makes them feel loved, others feel guilty and feel like their being given sympathy. , Bite your head off? No he will either say yes, no or I'll think about it (if the later, don't let him leave you hanging indefinitely; move on).

    Only ask if you really like him! Don't do it if you're just making it up! If he gives you something, try to give him something back the next day. , He may be with his friends more often than when he is with you.

    This is normal, and part of a healthy relationship! , If he sees that you care and want to see him more often, he may become more committed to the relationship. (Try to have a few activities in mind to do together, like playing video games, baking brownies, watching a favorite show or movie, shooting hoops at the nearest basketball goal, etc.) , Depending on the sort of guy he is, if he comes around to your house, find a comfy spot and lean in.

    Boys love kissing! However, if you aren't comfortable, don't force yourself. , You want to keep in touch with him, but not 24/7! He might think you're a nag, or that you don't trust him.

    Text him once or twice a day, if he responds, YAY! But you can't expect him to.

    Also, if you see him in the hallway just say hi.

    If he stops you to talk, stay there and have a short conversation or tell him you'll talk to him at lunch. , If he is mean, cruel, or disinterested, just move on.

    He may be cute or cool, but it's just not worth being mistreated to try to pursue him.

    Pick someone new to like.

    Always remember that boys don't control your happiness.
  3. Step 3: Talk to your friends about dating in general.

  4. Step 4: Move to the next phase if you think that dating is for you.

  5. Step 5: Find out what this boy is like before assuming that he is date-worthy.

  6. Step 6: Hang around with this boy and his friends.

  7. Step 7: Make a beeline for the boy.

  8. Step 8: Be a sweet and kindhearted person.

  9. Step 9: Get to know him on Facebook

  10. Step 10: Twitter

  11. Step 11: Instagram or whatever happening social media site is in your wee part of the world.

  12. Step 12: Don't stalk the poor chappy.

  13. Step 13: Decide if he's worth asking out.

  14. Step 14: Decide when the time is right.

  15. Step 15: Decide whether you'll give him hints before asking outright.

  16. Step 16: Find the brave in you and ask this chappy out.

  17. Step 17: Keep your request to date this boy simple.

  18. Step 18: Be ready for either a yes or a no.

  19. Step 19: Tell him that you like him and would like to be his girlfriend

  20. Step 20: What's he going to do?

  21. Step 21: Understand he won't want to be with you all the time.

  22. Step 22: Invite him around to your house.

  23. Step 23: Kiss him.

  24. Step 24: Don't seem too desperate.

  25. Step 25: Don't stay with this boy if he doesn't treat you well.

Detailed Guide

There is no magic number or time at which a person is ready for dating.

It's dependent on who you are, how mature you feel and what your parents think about it too.

Indeed, it's a combination of factors.

At this point, don't feel bad if you don't actually feel like dating yet––that's okay to, you can have friends instead of dates too and nobody will think any the worse of you for it.

Take a little time to better understand your own motivations for having a boyfriend or going out.

How big a factor is each of the following for you: wanting friendship/companionship and someone to hang out with; wanting to have someone else interested in your well-being and listen to your worries and joys; wanting affection (hugs, touch and nonphysical affection, romance, etc.); wanting to be accepted and cool and not seen as a loner by schoolmates? Which of these are your main motivators? The better you understand your own needs and motives, the better your decisions and choices will be about whether to ask a boy out, and if so, who to ask, and how to do it.

Taking the time to introspect and understand yourself better is a lifelong process important for adults as well as for middle school students.

If they don't think that dating boys is appropriate right now, they mean it and they have good reasons.

Listen to them and just find friends instead.

There's plenty of time for love later.

If you're parents are cautious but open to the possibility, explain how responsible you'd be if you went on a date, such as meeting curfew times, letting them know where you are going and being reachable by phone at all times. , Ask them what they think about dating and how comfortable they feel about it.

While you don't need to agree with what they say or think, it can be helpful to gauge their feelings and get ideas to form your own thoughts. , Once you're happy that you're ready to date, try getting to know this boy better. , He might not turn out to be the kind of person you first thought.

It makes good, common sense to get to know him a little before asking him out.

Fortunately, there are plenty of ways you can use to get to know this great person somewhat better. , Make it a group thing.

Get your friends and his friends to mingle at recess, lunch and after school.

Make it all seem most casual, and just hang about chatting to everyone, including him.

Make friends with him and his friends.

It will make him feel closer to you without realizing just yet what your real intentions are.

This gives you the space to study him close up and kindly. , Have casual conversations with him about school, sport, your uniforms, school rules, anything really that is simple, relevant and easy to chat about.

Find out what interests him and let him know just a little about what interests you.

Here are some conversation starters: "Want some gum?" "Hey, do you have any gum?" "Okay, no more projects on cells.

Mine looked like it came out of a horror movie!" or "Random Question: are you a morning or night person?".

If you are in different years/grades, ask him what he thinks you'd like next year.

Don't chew his head off with "me, me, me" talk though.

Instead, make the aim to learn as much as you can about him.

He'll ask you enough things in time. , Give him little gifts now and then, such as chocolates.

But be sure to give them to his and your friends at the same time.

You're trying to prove you're a generous lassie, not someone focused only on him––that comes shortly.

For now, show him what a great spirit of generosity you are. , Send a friend request and bond online.

Send casual messages, jokes, funny pictures and nice sayings.

Keep it light and friendly and include your other friends initially so that he looks like he's just one among many recipients of your online banter.

As time goes on, you may grow to feel comfortable just chatting or messaging him. , He doesn't want to know what you're doing every five seconds and he certainly doesn't want to have answer to you about what he's doing every five seconds.

Instead, just get to know his schedule, work around it with the occasional "hello"

"how's it going" and "wow, isn't funny how we keep bumping into each other?" moments.

If you're online, take the chance to now and then send something with a "when I saw this, it made me think of you, 'coz I know you like the LOL cat/etc. pictures". , Do you want him to be your boyfriend? Before you ask him out, be sure he's the one.

Before you decide that you're in love, know what your own feelings are.

Make a list of the negatives and positives about him, and then decide. , At least have inkling that this guy has grown fond of you and is somewhat into you.

Signs include him breaking the touch barrier, lingering gazes, fond nicknames, making excuses to be near you, texting or messaging you a lot, blowing you kisses and generally being sweet to you.

In some cases, he might be a little more brash and teasing toward you, because he feels comfortable around you.

If you've gotten the impression that he's keen, it might be time.

Ask him when you feel right and comfortable! , If so, flirt a little, make eye contact more often and pass a few sweet notes to him in class.

Make it clear that you're keen on him. , He's yours for the taking if you've noted the signs correctly and feel you know him well enough by now.

Rehearse asking.

If it helps you to gain confidence, practice beforehand.

First, write down what you want to say.

Then, practice in the mirror.

Look at your body language and facial expressions.

Practice until you feel confident. , This is especially important at the middle school and junior school levels.

This isn't about determining your love match for life; it's about gaining a fun and carefree romantic friendship and the main thing is that you both feel comfortable with one another.

Say something like, "Want to go for a slurpee over lunch break?".

This is perfect.

Make sure his lunches are free first.

Or, casually ask "So do you have band/yearbook/practice, etc. today? Mind if I come too".

Or, "Hey, would you like to come with me to the movies/park/skate rink, etc. this weekend?" If asking him out over text message, say something like: "My friends think we should get married.

Spring wedding sound good?" Expect a "lol" as a response.

Then after he responds, say something like, "Yeah, but I really do like you." Do try to use full words as often as possible; text messages can look really stupid if you use text language (u for you, r for are). , Realize that he may need time to process your request to get together, hang out or go on a date, and that's fine.

Let him know it's fine and that he can get back to you.

If he says no, that's all right.

He's probably embarrassed, or he hasn't made up his mind.

Be understanding, and don't become defensive or act hurt.

Never stall or make excuses.

But at least he knows you like him and he might start looking at you in a different way.

If he says yes, say "great" and start planning your date, make sure you pay, unless he insists.

Some guys love it when the girl pays, it makes them feel loved, others feel guilty and feel like their being given sympathy. , Bite your head off? No he will either say yes, no or I'll think about it (if the later, don't let him leave you hanging indefinitely; move on).

Only ask if you really like him! Don't do it if you're just making it up! If he gives you something, try to give him something back the next day. , He may be with his friends more often than when he is with you.

This is normal, and part of a healthy relationship! , If he sees that you care and want to see him more often, he may become more committed to the relationship. (Try to have a few activities in mind to do together, like playing video games, baking brownies, watching a favorite show or movie, shooting hoops at the nearest basketball goal, etc.) , Depending on the sort of guy he is, if he comes around to your house, find a comfy spot and lean in.

Boys love kissing! However, if you aren't comfortable, don't force yourself. , You want to keep in touch with him, but not 24/7! He might think you're a nag, or that you don't trust him.

Text him once or twice a day, if he responds, YAY! But you can't expect him to.

Also, if you see him in the hallway just say hi.

If he stops you to talk, stay there and have a short conversation or tell him you'll talk to him at lunch. , If he is mean, cruel, or disinterested, just move on.

He may be cute or cool, but it's just not worth being mistreated to try to pursue him.

Pick someone new to like.

Always remember that boys don't control your happiness.

About the Author

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Amber Palmer

Professional writer focused on creating easy-to-follow pet care tutorials.

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