5 Significant Questions to Ask on a First Date

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No matter how great you are at dating, going out with someone for the very first time can make you nervous. You know why? You don’t know this person. You don’t know what they are like, so the uncertainty of what could be will leave you all up in your feelings. 

You are not the only one feeling that way. If it’s any consolation, your date is most likely feeling the same way because they don’t know what they are walking into either.

Having the right questions can make it a lot easier. Two people meeting up for a date can be very awkward if they don’t know what to talk about. Those silent moments when you’re wondering what to say next, and your date is also clueless about what to say, could be very uncomfortable.

A good way to go about it is to have a list of questions you would want to ask them. Not only will you get to know them better, but you guys will also have things to talk about without feeling awkward.

1. What Are Your Hobbies?

The first question you might want to ask your date is, "What are your hobbies?" Both of you are most likely to feel tense when you meet up initially because you don’t really know each other, so the idea is to help your date feel comfortable.

When your date is comfortable, their energy will rub off on you. To help them relax, ask them a simple question.

When you ask them about their hobbies, that’s a straightforward question because their hobbies are things they enjoy doing. By talking about their hobbies, their face will automatically light up as they begin to tell you all the things they love to do.

You can tell they are enjoying the conversation. You also get a sense of what they like to do. Naturally, they would want you to tell them yours too, and when you do, you will have a common ground to kick-start your date.

For instance, you ask them if they love to sing or dance, and they say they do, then they go quiet. You need to probe further. Some people are naturally calm and gentle. They’re not very expressive. You need to ask them follow-up questions.

If, for instance, your date says they love to dance, you could ask what kind of music they love to dance to. When they answer, you could also say something like, "Oh, you must be a very good dancer." Of course, you do expect them to laugh before even answering the question, and you can tease them about their dancing.

If they say they are good dancers, you could even say something about them teaching you how to dance one of those days. It just lightens the mood. You guys will be more relaxed and able to get on with the date.

2. How Do They Spend Their Weekends

A lot of people are busy at work during the week doing all the boring stuff, so you might not want to ask them about that because, of course, they are working. But the weekends are an opportunity for them to relax, socialize, and take a break from everything going on in their lives. Knowing how your date spends their weekend will give you an idea of who they are.

What do they do for fun? You can find out by asking them how they spend their weekends. Someone who loves to play football, tennis, or whatever would say they do so on weekends. If they love to party, for instance, they would also tell you that they party throughout the weekend. You need to know this because if both of you decide to take your relationship to the next level, you might be spending your weekends together. 

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If you’re not comfortable doing those things, you will struggle to fit in. It will be so unfair to your date for you to wake up one morning and ask them to stop doing all the things they usually do on the weekends just because you’re not okay with them.

By asking that question now, you will know whether you fit in. Both of you could exchange ideas. You could also tell them how you spend your weekends.

If you guys are into each other, you could start making plans for things you could do together on the weekends. Doing those things together could help you bond even faster and progress to other levels of your relationship.

3. What Was It Like for Them Growing Up?

You probably love what you see in your date. You think they’re a great person, but do you know what it was like for them growing up? Knowing what it was like for your date as a child will help you understand them better. It will give you a sense of their journey and how they arrived at their current position.

Talking about their childhood will help them relax and feel very comfortable around you, as they are talking about something very special to them. By telling you about their childhood, your date will be sharing a part of their life that is special to them. This is not something you tell just anybody. You don’t meet a stranger and start telling them about your childhood.

If both of you are within the same age range and probably grew up in the same country or location, there’s a chance you both indulged in activities that were popular there at the time.

Both of you will have some things to talk about, and it will make things a lot easier to know that this person did some of the same things you did as a child or went to some of the same places you did. You guys could even start talking about the jokes that were popular back then, the things kids your age used to do. It’s just a way for both of you to level up and keep things going.

When your date tells you about what it was like for them growing up, you will have something to talk about later on. You will have points to reference if you guys eventually end up dating, rather than knowing nothing about their childhood and being totally confused or clueless about what it was like for them as a child.

4. What Is Their Fondest Childhood Memory?

We all have fun childhood memories. Those memories make us happy and excited just by thinking about them. When you ask your date that question, you should be ready for a swell time because you will bring back exciting memories of their childhood.

By sharing that memory with you, your date will be sharing a special part of their life. If that memory stands out among all their other childhood memories, it means there’s something about that memory, something very significant about that occasion.

If you take a critical look at it, you can make out one or two things about the kind of person your date is. Why is that incident so significant to them? Why can’t they forget that incident? By sharing it with you, you will come to understand what truly makes up their personality. This is something deeper than most people realize. 

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Whatever question you ask your date, it’s only fair to provide the answer, too, even if they didn’t ask you. As you’re trying to get to know them, they’re also trying to get to know you. Sharing your fondest childhood memories with each other will probably be the highlight of your date and help you bond much better.

5. If Money Weren’t a Problem, What Would They Be Doing?

Money is a constraint for a lot of us, and sometimes we end up doing certain things just because we don’t have a choice - we have to earn a living.

If your date didn’t have to worry about earning a living or money, what would they spend their time doing?

This is very important for you to know because it could actually happen. We all pray for better days, breakthroughs, and moments that will change our lives. It’s only fair that we’re optimistic that such a day will come. When that day comes for your date, how will they be living their lives? It’s a first date with no guarantee you’ll be in their life when that time comes, but if you’re there with them, you’d want to know what they’d be doing.

Whatever they’d be doing, you want to make sure it sits well with you. Otherwise, both of you will have a lot of conflict because you wouldn’t want to associate with it.

As you ask that question, you need to pay close attention and don’t forget to answer it. As you both answer that question, you need to find common ground.

If both of you would rather be doing things that are entirely different if money weren’t a problem, then there’s a disconnect. You want to be with someone who shares some values with you, not someone who is the exact opposite of who you are.

A first date is meant to be memorable. Don’t be so hard on yourself. Relax and let things flow.

Don’t come on too strong on your date. You want to get to know them and understand what they’re all about, but this is just a first date. Asking overly personal questions will make them feel uncomfortable. They might not want to share those details with you right now, so give them time. Hopefully, you guys will have many more dates to get to know each other better.


Chris O

Chris is a writer and content creator. He's passionate about creating informative and engaging content. Check out his YouTube channel at https://www.youtube.com/@ChrisOdogwu1 for more engaging content.

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