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Best New Relationship Questions to Ask a Guy

Half the problem on a date is keeping the conversation flowing. Unfortunately, most of the time that’s up to you.

How many times have you found yourself carrying the entire conversation while the guy you’re with sits across from you, sips his drink, and nods every so often?

You wonder what would happen if you refused to play the game and did exactly what HE did: sat back, relaxed, and waited for him to pick up his end of the conversation.

Well, with the right questions, you can!

You can turn the conversation over to him and let him do his fair share of the work.

With a handful of interesting questions to ask a guy, you won’t find yourself wearing out your voice in a nonstop monologue. He’ll be responsible for filling the silence.

So what questions should you ask?

It all depends on what you want to achieve.

Best Question to Find Out What He Does

You’re on a date to have fun, not talk about work.

But if you’re curious about what he does and you don’t want to ask the obvious question, you can ask him this instead:

  • Working on anything exciting lately?

You’ll learn what he thinks about his job (maybe there’s nothing exciting about what he does!) and what his work actually entails, details that will tell you so much more than a job description.

If he’s the kind of guy who doesn’t like talking about work, he may shut down your question. Try following up with this instead:

  • What’s a typical day look like for you?

Best Question to Learn about His Childhood

A person’s childhood can tell you a lot about who they are as an adult.

But predictable questions like, “Do you have any siblings?” or “Does your family live close?” aren’t going to get you very far.

Here’s a much better question that can be more revealing than he realizes:

  • What were you like as a kid?

And if his answer doesn’t tell you as much as you’d like to know about his family, you can ask:

  • What family member are you most like?

Best Questions to Find Out If You’re Compatible

You might think that compatibility comes down to liking similar things, but online dating site OkCupid has done the research.

They discovered that the questions that predict whether you’ll go on to have a relationship have nothing to do with your favorite foods.

One-third of successfully-matched couples agreed on all the answers to these three questions:

  • Do you like horror movies?
  • Have you ever traveled around another country alone?
  • Wouldn’t it be fun to chuck it all and go live on a sailboat?

Best Question to Suss Out Dealbreakers

Everyone puts their best face forward on a first date.

But you need to know more than his good qualities. You need to know what makes him tick. You need to know if he’s withholding anything for fear of scaring you off.

This question may not give you all the answers, but it’s a good start:

  • What’s the most important thing I should know about you?

Best Question to Make Him Like You

The more he enjoys being with you, the more he’s going to want to see you again.

So how do you make sure he really enjoys your company?

The research is in. The secret is to ask him a question that evokes a positive feeling.

When he recalls something positive that happened to him, his mood gets an immediate boost. He feels better—and he associates that positive feeling with YOU.

So don’t ask him how his day went. Ask him one of these questions:

  • What’s something good that happened to you today?
  • What’s been the best part of your week so far?

These questions are by far the most powerful questions you can ask a man on a first date.

Ask him about something good that happened within the first 10 minutes, and you’ll prime your conversation with positivity.

Which of these questions do you think you’ll ask on your next first date? Happy dating!


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