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Did it help build an emotional connection between the two of you? When was the last time you cried, and why did you? Questions to ask a guy 1.

Are you happier single or in a relationship? Would you rather be smart or happy? Ask him to share what he wants and needs from a romantic relationship.

They say alcohol, anger, and how someone handles money tells you the truth about who they are.

Do you think some people really have psychic abilities? Are you a spiritual or religious person? You can take this further by asking of his favorite team.

What is the ideal dream date according to you? What are the things a man should have in him when he is in a relationship? What is one thing you never get bored of? Or does he struggle to let go and live outside of the box? How does he keep going when the going gets tough? Is there anything that you are insecure about? What could he absolutely not live without … and conversely, what would he be willing to give up? Do you think I can be your ideal girlfriend? What skill do you wish you could master? This question can have a million different answers, all fun to talk about.

Have you ever been jealous? What are people always surprised to discover about you? What event would you rather die than live through? For example, if a guy went to the movies today, ask him what movie it was, whether he liked it, etc.

Do you like active leisure? — Again pay attention to his answer as it gives you and insight to his preference.

If he tops them with you, you know he likes you.

Are you a competitive person? Have you ever had sex in a forbidden place? You can also take this further by reversing the question.

Are you a shy person? What are your biggest life goals? How do you picture your life? Who is the one person you go to when you need advice? We've already thought up some but here are some personal and random questions to ask a guy! Do you prefer making plans or following along with what someone else planned? What activity makes you feel at peace? What is something you think should be illegal? If you had the option to hit restart and begin life all over again, would you? Here are 10 personal conversation starters questions to ask a guy: 14.

If you could go on a date with any female celebrity, who would it be? What is your biggest fear?.