5 Ways to Ask A Shy Guy Out on A Date

4. “Can you teach me more?” Ask for a small favor.

If you happen to know his forte, ask him to teach you more about it. Show your enthusiasm and interest and let him know this may take longer than just a brief chit-chat in the hallway. You may even want to invite him to Starbucks and see where things take you. The only challenge to this ploy is that you have to know his areas of strength and be prepared with plausible questions.