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The Proven Secrets To a Great Date


Before you meet that next potential suitor, I want you to think about questions to ask a guy on a date.

Asking questions is a great way to get to know someone quickly, but asking the wrong questions can make him feel like you’re interrogating him.

Instead, I want you to focus on questions like the following as a way to develop the conversation on that date, not interview him as your next husband! In a moment, I’m going to go into different types of questions to ask a guy on a date, but first, let’s address why you need to even care about this.


Why It is Crucial To Know What Kind of Questions To Ask a Guy On a Date

Why do you even need to worry about what questions to ask a guy on a date? Why does it matter?

First of all, you don’t want to waste your time. If you and a man aren’t on the same page in terms of values or what you want out of life and love, there’s really no point in spending more time together.

Let’s say you love your hometown and see no reason why you should ever leave it. You’re on a date one night, and the subject of travel comes up. Your date tells you that in six months, he’s moving to Timbuktu. Isn’t that kinda important for you to know about a guy you’re considering dating and investing emotional energy into when clearly there’s no long-term potential??

Yea, a bit.

And another reason to think out what you want to bring up on a date: you want to avoid coming off as an interrogator…yet you want to read into what this guy is all about. The right questions (which we’ll cover here) will help you get insight into who this man is without making him feel like he’s being grilled.


Some of the following questions to ask a guy on a date work well on a first date, while some (like those pertaining to finances) you should save for the third or so date. After that, it gets easier to ask questions as you know him better and better. Let’s dive in.

Questions to Ask a Guy on a Date to Get to Know Him

Most people are nervous on their first date with someone new. You may be at a loss for what to say. Having some questions in your back pocket can make for icebreakers that warm up the date and help you get to know the guy you’re with. These aren’t your typical have you ever been married questions, and that’s a good thing. Your goal here is to ask open-ended questions that invite him to start a conversation without freaking him out. Try questions like:

  • Who has been the biggest influence in your life?

  • If you could live anywhere in the world, where would it be?

  • What makes you laugh?

  • What are you passionate about?

  • What are your three favorite things in the world?

  • Where are you from originally?

How these questions help you figure out compatibility: Like I said earlier: you want to know what a man is all about without giving him the third degree. Questions about what makes him tick and his experiences can actually tell you a lot about his personality. Does he eagerly answer your thought-provoking questions, or just shrug his shoulders and say I dunno? The first one is a guy you want to continue to get to know. The second? Well, be honest: do you really see potential there?


Questions to Ask a Guy on a Date to Learn About His Family

Family values are important for most of us when we’re looking for a life partner. Is he close to his family? Does he have a similar upbringing to you? Or one that’s completely opposite?

Usually, asking someone about their family is a great way to get them to open up (unless there’s some tragedy or drama there. Still, if that comes up, it could be a red flag for you to pay attention to.). Even if he’s just telling stories about wrestling with his brother as kids, you can still glean information about who he is as a man.

Here are a few questions to ask a guy on a date about his family:

  • What was your family like growing up?

  • Does your family live here or somewhere else?

  • Who in your family are you closest to?

  • What is a tradition your family had when you were a kid?

  • Do you have any siblings?

  • Are you more like your dad or mom?

How these questions help you figure out compatibility: From my experience working with women, most of