8 Revealing Questions You Can Ask Him on a Date

Dating is tough. The person we’re meeting up with may have been on multiple other dates this month. How can we stand out when there seems to be so much competition?

In today’s video, I cover the “what to say” part—specifically, how to stand out by asking one of 8 tried-and-tested questions I’ve put together for you. 



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Hey everyone. I wanted to give you something super practical today, eight questions you can ask on a first date to get beneath the surface, out of small talk. Learn a bit more about who someone is. See if you are compatible with that person and in the process, make you appear more interesting, and likable and unique to the person you’re on a date with. Pay particular attention to question number eight, because if you do it right, I think that question is the most revealing about a person. By the way, if you haven’t already go over to YourDatingSolution.com, where I have a tool that allows you to input your dating challenge right now and it will recommend you the solution of mine that best fits where you are in your love life right now go check it out now. YourDatingSolution.com.

Okay. Question number one, who is someone you really admire? I believe that when we ask someone who they admire, we start to actually learn their values. What is it they value? What traits do they think are important in another human being? Because that says what traits they feel are important for themselves to aspire to. By the way, the key to this question is asking why. What is it about that person? For me Jameson Mr. Rogers and Steve Irwin. Mr. Rogers because of his just kindness that was consistent in every situation and Steve Irwin because of his just insane passion for what he did that made you get excited about whatever he was doing because of the energy that he fired out like a cannon. Ask your date next time, “Who’s someone you really admire?”

Number two, “What kind of vacations do you love the most?” I think this is just a fun question in general, because it gets you talking about something fun. It gets you away from work. Even if someone hasn’t taken a vacation in a while, it just gets us into that kind of fantasy of where we like going, what we like doing when we are being carefree. Oh as a follow-up, you can ask someone, “If you had to spend a year in a different country altogether, where would you choose?” I think I would choose Japan. By the way, with all of these questions, you get to ask why? What is it about that place? And what’s more fun than describing the soul of a place that you love.

Number three, “What book do you think everybody should read?” This book for me is Four Thousand Weeks by Oliver Burkeman, which talks about basically FOMO on an existential level. The fact that we don’t have enough time in life, there’s so much we want to do and that leaves us all overwhelmed, and despairing and constantly doing too much. I love this question. What book do you think everyone should read? ‘Cause it’s another way of saying what’s a message that you think everybody should hear. When you hear the message that someone thinks everybody should hear, then you are learning what they think is really important in life.

Question four, “What do you love most about what you do?” Now not everyone loves what they do, but what you’re going to learn is A, whether they are passionate about what they do for a living and B, even if they’re not, can they find something that they love about what they do? If they say oh mate, I really struggle with what I do. I’m not enjoying it. Then say, “What do you want to do instead? Or is there something you’d much rather be doing?” Then you learn about something they’re moving towards. But you are seeing if they can find passion in things. I always think that it’s a bit scary if someone says, I don’t like what I do. Then if you say is there something else that you’re working towards that you would love to do and they say not really.

I would find that troubling, because I’d think, oh, we don’t have a lot in common. I could live with the fact that you don’t enjoy what you’re doing now as long as you were working towards something that you did enjoy. But the fact that you’re doing neither scares me because it makes me feel like we have a different passion towards life, or we have a different standard for passion in our lives.

Number five, “What’s something you love doing, but don’t do enough?” Traveling, probably everyone’s answer right now after the last two years, I realize. Not just mine. I almost feel like this activates a part of our brain that really loves doing something and gets excited when we think about it or when we talk about it. But maybe we haven’t gone there in a minute. You’re inviting them to tell you about hobbies or passions that they’re not indulging nearly enough and so you learn what their thing is.

Number six, I borrowed this question from my dear friend and publisher Karen Rinadli, who wrote a book called It’s Great to Suck At Something. The question is, “What do you suck at?” By the way, you can even use Karen’s book as the inspiration for this question. You can say there’s a book that I saw on the bookshelf recently called It’s Great to Suck At Something and it got me thinking what do I suck at? What do you suck at? When you ask that question, you invite someone to a place of humility that a lot of people can’t go to. A vulnerability that a lot of people aren’t comfortable with, but I like being around people who can be vulnerable.

Can you have a moment of actual vulnerability? I suck at karaoke. I get very shy when I’m in an environment where I might be called upon to do something like that. Some people, they’re like a duck to water when there’s a microphone around. I am the opposite of that and it’s probably because I can’t sing.

Number seven, “What is a film you are embarrassed you like so much?” I had to really think about this one. Deep Blue Sea. That is a pretty bad movie. For some reason, Deep Blue Sea. There can’t be a screen that Deep Blue Sea is on that I don’t end up watching for the full two hours. I just think this question’s fun. I also think you find out how seriously a person takes themselves.

A bit like asking someone what’s the most embarrassing song, if I looked at your top 25 most played songs, what would be the most embarrassing one among them? Firstly, it’s adorable to learn something that someone listens to or watches that’s bad, but it’s also revealing of their ability to laugh at themselves.

Number eight, now this is the one I said I think is the most revealing. “How would your closest friends describe you?” What I like about this question is it gives someone an unselfconscious way to talk about themselves. It’s very hard. If you say to someone, describe yourself, that’s really difficult. Most people are too self-conscious to do that. But if you say, how would your best friend describe you? Then you’re allowing that person to ventriloquize the person that knows them the best and say things from an objective standpoint, from some distance that actually say things about themselves.

Now of course, all of these questions, one of the things they do is they give this person a platform to talk about things that are important to them. Things they love, things they connect with. It does it in ways that a lot of people don’t ask. So inherently you giving someone a platform to talk about all of these things that they enjoy talking about is going to make you more interesting to that person.

I also want to add that it’s incumbent on us to have good answers to the questions we ask. Anytime you’re going in with questions like these have a sense of if someone asked me these questions, I would have rich and interesting opinions and things to say about the very things I’m asking. I’m not asking someone else to be interesting without being prepared to be revealing, and vulnerable and interesting myself.

Don’t forget to go over to YourDatingSolution.com if there’s a particular challenge you’re facing in your love life right now and you want to know what I would recommend for that challenge. It’s all there waiting for you. Don’t forget, leave me a comment today. I want to read them. Like this video, subscribe to this channel and hit the notification bell said that the next time a video comes out, you are the first to be notified. I’ll see you next week.