Finding a Place to Meet
Spend time near the places they hang out. Get a sense of the kinds of places they hang out either inside or outside of school and ask your friends to meet up at nearby places. Getting close will set the stage for possible encounters. Don't follow or stalk them! Just identify a few key places you could meet: near their locker, their lunch table, or a club they go to after school.
Stand next to them in line. Standing in line offers opportunities to strike up a conversation. It gets boring waiting in lines, and this makes people more open to talking to individuals they don’t already know. School lunch lines, long lines at cafes, and waiting for rides are good chances to catch their attention. You can say something like, "I think I'm going to die of boredom if you don't help me. Know any jokes?" Or if you're in a lunch line, you can open with your own joke by saying, "Mind if I cut you? I'm really hungry."
Bump into them in the hallway. When you see them coming down the hall, walk towards them while pretending to read something or talk to a friend. When they get close, gently bump shoulders to strike up a conversation. You can apologize sincerely, ask if they're okay, and then introduce yourself. Or you can be more flirtatious. In an exaggerated and clearly playful manner, pretend to be hurt and ask them why they ran into you. Then make it clear that you were kidding and introduce yourself.
Asking for Help
Get help carrying something. Select an awkwardly shaped or heavy item. Walk past them while struggling to carry it. When you see them, smile and ask for help. Ask sincerely, or you can have fun with it by putting the item down and casually gesturing for them to get over there as if you already knew them.
Spill or drop something when you’re nearby them. If they're near you in class, drop a pencil near them. Or if you’re feeling bold spill water or soda, so you’ll have a chance to chat while cleaning it up. While you're cleaning it up, make a joke about being clumsy. Say something like, "You don't understand, I do this all the time. Hey, you know, you cleaned that up really fast. You should come to all my classes with me."
Enlist their help resolving a humorous debate. If you see them nearby, strike up a debate that you know will divide your friends--like which sports team is better or what’s the best brand of chocolate. After debating for sometime, announce that you need an outside opinion and walk over to your crush to ask them to settle the debate. This approach works best if the debate is humorous or absurdly silly in nature. If you’re too scared to approach them, you can ask a friend to do it but make sure the group follows her!
Ask them to take a picture of you and your friends. Pose with your friends and then ask them to take the picture. Not only will it make total sense to talk to them for this reason, but it shows them you’re social and fun-loving at the same time. Be sure to thank them after you take the picture. If this is at an event, ask them if they're having fun.
Ask them to sign a petition. There’s always something that needs improving at any school or organization. If you’re the kind of person who gets passionate about issues, then you can start a petition. When you ask them to sign it, you’ll have a natural conversation starter that you can build on. Be respectful of their reply. If they tell you that they don't want to sign the petition, don't push them or pester them.
Using Common Interests and Mutual Friends
Use social media to connect over shared interests. Don’t just send a message out of the blue. Instead, learn as much as you can about their interests by scrolling through their feed, pictures, and posts.Then reach out to them indirectly by liking or commenting on one of their posts. To make a comment seem less random, ask mutual friends to tag you in pictures or posts for a few days beforehand, so they'll have a chance to learn about you. Lots of relationships work because the couple share values and interests, so that's something really important to look for.
Ask a mutual friend to introduce you. Getting an introduction works best when the friend mentions something that you both have in common.This will provide you with a conversation starter. A friend could say something like, "Pat, have you met Jamie? You're both totally obsessed with Star Wars, by the way."
Use their possessions as conversations starters. Pick an item like a computer or a book they're reading. It helps if you know a lot about the item or topic. Begin by expressing interest in the item. Then move on and compliment something about them. Start by saying something like, "Is that a new smartphone? I really like the decal on the case. Did you draw it yourself? And after staging a few fun meetups, you might be ready to tell your crush how you feel! Just remember to be open, honest, and respectful of whatever their feelings may be. Reader Poll: We asked 456 wikiHow readers about the best ways to ask out or confess feelings to someone, and 82% agreed that it’s best to have a face-to-face conversation about your romantic interest. [Take Poll]
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