Approach him when the time is right, but don't go out of your way to flirt with him. If you leap at every chance or create excessive opportunities to flirt with him, you will appear too aggressive.
Gage where he is. Ask simple questions, such as if he's in a relationship, dating, looking for someone special or taking things one day at a time. His response will help you flirt within appropriate boundaries. If he is in a relationship, you should move on to someone who is available. If you are uncomfortable asking questions directly, you may say something like, "Dating is so hard these days. What do you think?"
Ask him questions about his interests, and find things the two of you have in common. Keep things light, asking about movies, hobbies or current pop culture events. Avoid political discussions or hot button issues, as this can take things from flirtatious to heated quickly.
Compliment him. Tell him things you like about him, but keep your compliments PG-rated, as sexual references can be too much. If he is wearing a nice outfit, say "I love your outfit today" rather than "You look amazingly hot in that tight shirt right now."
Joke with him. Light teasing is appropriate when flirting, as is joking. Make jokes about things you have in common, but don't reach to make things funny. Only make jokes about things that are relevant, such as a funny story about what happened to you over the weekend.
- Ask him for his number, and send flirtatious yet nonsexual text messages once or twice a week to keep him interested.