40. Your First Time?

Everyone remembers their first time no matter how much they try to forget. Finding out about a guy’s first time is fun but a personal question. He might still have fond memories or has a funny story to tell. It’s probably a short story but funny nonetheless. It’s an intimate question that’ll lead to a deep conversation. 

41. What Is Your Dirtiest Fantasy?

A flirty question is a great question to ask a guy. First of all, guys love when girls flirt. However, it’s also a revealing question that’ll tell you more about their emotions, fantasies, and kinky side. Plus, dirty questions can lead to all sorts of fun places. A popular response most guys give is role-playing. Depending on their age, they’ll say Princess Leia in a gold bikini, C.J. Parker running down the beach, or Harley Quinn with a bat.

42. What Does It Mean To Say “I Love You?”

Saying “I love you” is a big moment for any relationship. However, the conversation about the phrase shouldn’t come too early. It’s a fair question to ask a guy and gives great insight. Some guys might have said it in the past and not meant it. It’s also possible the question will lead to a discussion about a past relationship. It’s one of the biggest questions to ask a guy.

See more about – The Top 101 Best Questions To Ask on a First Date