Fun Questions to Ask On A Date

Going on a date can be exciting but it can also be a little awkward especially if it’s the first date. Whether it’s for the very first time or the 100th with your spouse, there are certain questions to ask on a date that makes the encounter worthwhile.

In this article we’re sharing with you ten questions that you can use on a first date, or really any date, to help you be more connected and more ignited.

You know, when we go on a date, right, there’s always this conversation line that happens and at some point, it either gets awkward and disconnected or it gets fun and more connected. So let’s first talk about what makes it awkward and disconnected.

What not to do on a date:

Usually, this is when you run out of things to say. So many people do this where they just fish for fact. Facts are boring. Facts don’t create any newness or any variety, and guess what?

Most people when they go on dates, they fish for facts like such as the work you do and how long you’ve been doing it or been working there, whether you have any brothers and sisters.

It kind of looks like this: “So where do you work? How long have you worked there? Do you enjoy it? How many brothers and sisters do you have? Where did you grow up? Sure has been nice weather this week. …”

And the challenge with that is it really doesn’t give you a whole lot of information, whether or not the person you’re on a date with is a good match for you because facts are really one dimensional as far as revealing who that person really is.

Now, the other mistake people make, (and this was actually more my style of mistake) is they get way too intense and they become the interrogator. I would go on dates and women, at the end of the date they would say, “God, I feel like I was on a job interview,” or like, “What? Do you work for the FBI?

Like why are you asking me these questions?” It kind of feels like this:

• So, what do you want for your love life?
• What’s your longest relationship been?
• Why did it end?
• What do you see for yourself five years from now?
• Do you want kids?
• What are your religious beliefs?
• Where do you want to live if you were to ever get married?

Not a good strategy. Not at all.

You can see how that leads to disconnection.

Questions to ask on a date – a better strategy

So let’s talk about a much better strategy to use, and that is asking high quality questions. High quality questions lead to higher quality date experiences in your life because these kinds of higher quality questions do two things that are great.

Number one, they keep things interesting and fun because they’re a pattern interrupt. Remember, routine feels boring. If you’ve done something over and over and over again, if you’ve answered the same question a thousand times, that’s boring.

But a new question that ignites your imagination keeps it fun and interesting and therefore generates a better connection.

Number two, the other thing that it does when you ask great questions is it helps reveal who the person is that’s sitting across from you or sitting next to you on this date because facts just lead to their past and what they’ve done before, but when you’re able to ask great questions, that helps reveal his thinking process, right?

What does he value for himself in his life? What does he want moving forward? What is his future like? When you’re able to understand those things on those levels, it’s much more revealing about what kind of partner he’s going to be for you.

So let’s dive into these ten questions and how to use them.

10 questions to ask on a date

The first way that you want to use them is you don’t want to use all ten questions on the first date, or even in one date. It’s like too much. It’s overwhelming. Just pick a couple that you want to use and use it at a strategic time. So I’ll tell you when that time is going to be.

The second thing is just be open to his answer, right? These questions are sort of off the wall, so be open and just observe how much he wants to lean into these questions or not and respect whatever answers he gives. They’re supposed to be fun, right?

The third tip is to have fun when you’re asking these questions. The more fun you make it for yourself, the more fun it’s going to be for him on this date.

So here’s when to use these questions, right? Chances are you’ve emailed a few times, you’ve talked on the phone a few times, you’ve gotten to know each other a little bit.

So when you’re meeting on the date, you’ll go through your niceties and you’ll say, “Hey. Hey, it’s good to see you. How’s your day today? What’d you do today?” and you kind of go through the beginning.

You don’t want to use these questions right upfront there. You want to save these for a little bit later because eventually, the conversation might get to this place where there’s a lull in the conversation where there’s potential like awkward silence and like, “Well, we’re not really connecting,” and that when you want to pull out these interesting questions.

And you can use this line. It actually comes direct from the movie Before Sunrise because it’s brilliant. And you can say, “All right. It’s Q&A time. We’ve known each other a little while now so let’s ask each other a few direct, random questions and the catch is that you have to answer 100% honestly. Are you game?”

And you kind of say it like that, a little tongue-in-cheek and playful and fun and when you preface it like that, that immediately ignites fun and interest into the conversation. It’s a total pattern interrupt.

Chances are the person you’re with has never had anyone say that to them on a date and so they’re like, “Yeah, I’m game. This is interesting. All right.” And then you just pull out one of these questions and fire away.

Now when you ask these questions, changes are they’re going to ask you right back what the questions are and that’s going to get the conversation rolling.

So let’s dive into ten questions to ask on a date. Again, pick the ones that resonate with you. You don’t have to use all of them, but use them at the right moment and it’s going to go really well.

Question #1: “What was the first time you remember having a sexual thought? Your first memory of that”.

And the person’s either going to lean into that or they’re not. You’re going to get a lot of information right out of the gate with that question.

Question #2: “Tell me about your most awkward kiss. What was your most awkward kiss that you’ve ever had?”

Question #3: You can set it up with, “Okay, here’s a random question: what was one of your most favorite vacations growing up as a kid?”

Question #4: “Okay. If you won a $250 million jackpot lottery, what would you do?”

Question #5: “If you could relive one day in your life, which day would you choose and what would you want to experience?”

Question #6: I personally love this one because it’s off the wall and it’s weird and you get a good feeling for what the other person is all about.

You say, “Okay. We’re going to give each other rapper names right now, okay? You’re going to give me one and I’m going to give you one. What is my rapper name?” And you just see what they come up with, right? And then you give them a rapper name and the more funny, the more off the wall, the better.

Question #7: “If you were told that you had one month to live, what would you do? How would you spend that month?”

Question #8: “Tell me this. What’s a book or a documentary film that you’ve either read or watched that had a significant impact on your life?”

I love that one because I’m a person who loves to grow. I love to read, I love to study, and I also allow myself to be inspired and impacted by things, and so I’m highly interested if someone else is the same way.

Question #9: “If you could trade lives with one person (it could be anyone) for one day, who would it be and what would you want to experience?”

Question #10: “If you could marry any fictional character you’ve ever seen, who would you marry and why?” I think that’s awesome.

I love that question. I was thinking about that for myself. I think mine would be Ariel from “The Little Mermaid” Yeah, man. She’s beautiful. The red hair just gets me. The red hair’s awesome. Love that.

So those ten questions are really going to support you in creating more connection and more fun on your dates. Go ahead and use them as you wish.

Again, pick and choose the ones that resonate with you. And you know, this is designed for first dates but you can also use some of it for a date you have with your wife or husband. Just make it fun and enjoy time together.