Here are 30 questions to ask a guy you're dating, because there's always question, it's sometimes fun to ask a question they're not expecting. 21 Questions to Ask a Guy or Girl You Kinda Want to Get With Questions to Ask Your Crush/New Bae. 1. What's your dream date night? Don't just ask a question; be sure to ask follow up questions to make the make it to a first date, asking for proof is another great icebreaker.