1. Mention something you like about the person, then make a vague and friendly proposal: “You always make me laugh. Would you like to go out sometime?” Have a couple of ideas in mind for what you could do, in case they say, “Sure. When and where?”
2. Mention an interest you have in common, and then make a fun and specific proposal (but stay flexible): “I like how we’re both into graphic novels. There’s an apple festival in my neighborhood this Saturday. Want to meet me there, eat some apples, and check out the comic store stand?” If they say, “I’m allergic to apples,” that might be a no, but it might be a real allergy. You could follow up with, “Would you like to go to a movie instead?”
3. Bring up an event you are already both going to, then suggest meeting early or going out alone afterward. If your crush is already a friend in your group, you might say: “After we all go out to the game, maybe just you and I could go get ice cream?” Or simply jump on the chance to let them know you care that they’ll be there.
4. Text or email a link to an event (movie showtimes, lacrosse game, etc.) along with a proposal that you go to it together. Follow up in person to prevent the awkwardness of going on a date in the flesh with someone you’ve only talked to about it electronically.