How to Ask a Boy out in Middle School

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Co-authored by Suzanna Mathews

Last Updated: February 24, 2025 Approved

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Getting to Know Him

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Asking the Question

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Has a cute boy in middle school caught your eye? Asking someone out is nerve-wracking, but there are some things you can do to make it easier. First get to know your crush, and then move on to flirting. You can ask them out in person if you’re feeling brave, or with a text message if that feels easier.

Part 1

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Getting to Know Him

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1
Talk to him casually about what he’s interested in. Ask him about any books, movies, or music that he likes—maybe you’ll find something you have in common. You can also just chat about the classes you have together. Finding a mutual interest can help you form a connection. ^{[1]
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- Try asking: “Do you play any sports?” or “What’s your favorite movie?”
- Start up a conversation in the hallway between classes or after school.
- Try some playful flirting to build a connection with him and make him smile.
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Find out if he’s available. If he’s already dating someone, or not interested in people of your gender, you can save yourself a lot of trouble by just being friends. If you’re not sure if he’s in a relationship, try checking social media or asking your friends. ^{[2]
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- Try asking your friends or his friends, “Do you know if he’s dating anyone?” This will make it pretty obvious you’re interested in him, so be prepared for that.
- You can also ask him directly, if you’re feeling bold: “Are you single?”
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3
Text or message online to get to know him better. Texting is a good way to flirt with someone, because you’ll probably be less nervous than when you’re talking in person. You can send him memes that made you think of him or talk about your day. If you have contact with him outside of school, it will let him know you are interested in getting to know him better. ^{[3]
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- Share a song you like or a funny meme.
- Try not to send too many text messages at once, and instead wait for him to respond.
4
Decide if you want to date him. Dating in middle school can mean many different things. It might mean you hang out with him with groups of people, you him text a lot, you eat lunch together, or that you hang out outside of school. There’s no one right way to date! It also might depend on how your parents feel about you dating. ^{[4]
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- If your parents don’t want you to date, try explaining that you will just hang out with him in groups, or that you will be back by a certain time.

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Asking the Question

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Pick the right time and place. Try to ask him out when he’s alone and not surrounded by friends. This will reduce the pressure on both of you, so it’s not a big public moment. If you don’t want to ask him in person, message him after school. ^{[5]
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- It’s probably better not to message at some weird time like 3 in the morning.
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Plan what you are going to say ahead of time. It can be stressful in the moment, so if you’ve planned what you want to say specifically, there’s less chance you’ll chicken out. It’s best to include a time in your question, instead of a vague, “do you want to hang out sometime?” ^{[6]
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- Try to be direct to avoid confusion: “You seem really cool. Want to go out this weekend?”
- You can also ask him to a specific activity: “Want to hang out after school sometime this week?” “Want to go get ice cream on Friday?”
- Try to avoid asking him to the movies for a first date, because you won’t be able to talk very much in the theatre. A dinner date might also be too much pressure.
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Give yourself a pep talk. It’s okay to be nervous when you’re asking him out. It’s actually a good sign, because it means you really like him. If you’re feeling scared, ask your friends for support. Write down 5 qualities about yourself that you admire. It might help to give yourself a deadline to ask him out, so you don’t keep putting it off forever. ^{[7]
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- Practice giving yourself affirmations like, “You can do it!”
4
Ask him in person, when there aren’t too many people around. Remember to smile and make eye contact. Start by saying hi and a casual question, like “how’s your day going?” Then move on to asking him out. If you chicken out the first time you try, just try again!
- Remember, you’ll never know if he wants to go out if you don’t ask.
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Ask him out with a text or a note if you’re feeling shy. Write the note ahead of time and fold it up. Give him the note directly, instead of passing it to him in class with a lot of people in between. You don’t want the whole class to read your note! ^{[8]
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- Keep it short and simple. There’s no need to write a whole love letter at this point.
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Be prepared for a yes or a no. If he says that he’s busy, but suggests another time to meet, then that probably means he’s interested. But if he says no, respect his decision. It doesn’t feel good to be rejected, but it’s something that everyone experiences in life, and it doesn’t say anything bad about you. ^{[9]
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- Keep your response really casual and chill if he's not interested. You could say, "Oh, well, that's a bummer. Good chatting with you, though." and leave it at that.
- It’s okay to be sad if asking someone out doesn’t work. Try talking to your friends about it and doing some activity that you love to take your mind off it.

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I like this boy name Brayden and part of me thinks he likes me back. He stares at me in class and he makes me laugh and I am not sure what to do first. Give him a note or say it in person? I am shy.

Zoe Mahony

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If you're feeling shy, giving him a note or sending him a text is a good option!

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Only ask him out if you like him. You don't have to date someone to be cool.

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If he’s already in a relationship, don’t ask him out.

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The advice in this section is based on the lived experiences of wikiHow readers like you. If you have a helpful tip you’d like to share on wikiHow, please submit it in the field below.

Follow his eye contact. If he looks you in the eyes and smiles a lot, he likely likes you back. If he looks anywhere other than your face or the ground, he might be nervous or only like you as a friend. And if he says no, give him a little time and then return to being friends.
Boys in middle school can be shy and quiet about their feelings. Make sure to ask him out privately and alone. If he says no, just say, "I understand" or something like, "I respect your opinion."
If you feel too shy to talk to your crush, write a note and give it to him. Or, ask your friends to tell him.

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