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.
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?”
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.
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.
It’s probably better not to message at some weird time like 3 in the morning.
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.
Practice giving yourself affirmations like, “You can do it!”
Remember, you’ll never know if he wants to go out if you don’t ask.
Keep it short and simple. There’s no need to write a whole love letter at this point.
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.
