If you want to know where he skates, ask about parks in town: “Where do people usually skate around here? Who goes to that park?” If you want try and know whether your crush is single: “How come he doesn’t have a girlfriend/boyfriend?” Ask about their friendship with him: “How did you guys become friends? What do you do together?”
You can be extremely casual if you don’t want him to know you like him just yet: “Hey, what’s going on, mind if I hang out with you?” You can be completely blunt and honest. This lets you know right away if he’s interested in you, and you can put a comedic twist on it as well: “Hey, I like you. Want to hang out?”
”How long have you been skateboarding?” This shows your interest in what he does and learning more about him. ”How often do you hang out here?” Not only will this tell you how passionate he is about skateboarding, but gives you a chance to know when you can next bump into him. ”What do you do when you’re not skateboarding?” This gives you a chance to find out about common interests the two of you might share.
Don’t always play it safe. Skateboarders like to take risks; try doing the same, within reason. Try an extreme sport or explore an abandoned building. Experiment. Leave your comfort zone and try things you were too scared to try. Conquer your fears and be adventurous. Go on spontaneous road trips or try a new hobby. Playful teasing. There’s a fine line between mocking someone (“That trick really sucked. ”) and teasing them (“Is that the best you’ve got to show me?”).
