5 Ways to Ask A Shy Guy Out on A Date

3. “I have been wanting to try this restaurant but I’d hate to go there alone.” A need for some company.

By emphasizing that you don’t feel comfortable being alone in a certain setting, he may feel responsible for accompanying you. If you look helpless, he can’t possibly say no to that. Make sure he doesn’t think you’re only kidding though. You may need to put on a damsel-in-distress act.