If you’re in school together, make jokes about the class or school in general. Friendly joking, especially if it’s complimentary, is a great way to break the ice and help someone overcome their self-consciousness.
For example, if she says that she would like to be an engineer one day, ask her exactly what type of engineering she’d like to go into. If she tells you something interesting about herself, respond in a sincere, complimentary way. For example, if she tells you she wants to be an engineer, say, “Wow, that’s so awesome!” Don’t push her if she doesn’t seem to be comfortable with a question.
Don’t interrupt her. Let her say what she wishes to say at her pace. Talk only a little about yourself. She can find out more later, and a little mystery is a great thing.
Sit with her in the cafeteria at lunch and simply chat about everyday life. Compliment her on her reading choices and talk about books together.
Ask if you can join her when she is hanging out with her friends. Don’t push it if she says no. She might think you like one of her friends if you put too much emphasis on spending time with them. Try to spend time with them only when she is around—at least at first. Say positive things about her to her friends.
Don’t overdo the compliments. One or two nice compliments to begin with is enough.
Don’t be angry with her if she says she’s not interested.
If she doesn’t like ice cream, suggest going out for lunch or dinner.
For example, you could say “I’ve really enjoyed getting to know you. I’ve come to like you a lot, and I was wondering if you would like to be my girlfriend?”
