What’s the nicest thing a woman has ever done for you?

Whether it was coaching him for an important class or giving him the perfect gift for his birthday, this is a conversation that will allow you to measure up. You don’t need to improve upon his amazing experience, but the gesture he discusses can tell you a lot about how others value him.

What do you think is the most impressive thing you’ve ever done?

A man loves to talk about his accomplishments, so be sure to give him space in a conversation to discuss the most impressive thing he’s ever done. Not only will this allow him to shine, but it will shed light on the kind of guy he is.

What do you think is something that reveals a lot about a person you’re dating?

Perhaps he thinks your charity work reveals a lot about your generous nature, or your intense gym schedule is indicative of a driven personality. The answer to this question is likely to vary, so listen intently.

What do you tell women about yourself to impress them?

We all have incredible stories that make us look amazing on paper. Although it’s unlikely that he’s saved someone from a burning building, hearing his most impressive story or anecdote is sure to leave you two with plenty to talk about.

What is one thing you never get bored of?

Is it long hikes during the summer or an intense session of video games? Something a man never gets bored of often speaks volumes about his hobbies and interests. If you can, suggest that you engage in one of these activities together. He’s sure to appreciate your willingness to be part of his world.

Would you ever change career paths or do you see yourself having your current job until retirement?

Not everyone is head over heels in love with their job. He may be happy with where he is, but if he isn’t, offer the support that will encourage him to move on and find something that he can’t wait to wake up for each morning.