Awesome First Date Questions to Ask Your Date

If you’re the type who usually is not armed with the right questions to ask on a first date, you may end up with a regrettable experience. Going on a first date could prove tricky.

While you might be excited with the thought of finally getting to be with your long-time crush. You often find out that you become nervous and unable to string coherent thoughts together. We understand.

Though this is quite normal with lots of people. However, it is important that you get past this mental barrier and engage in meaningful conversation on your first date.

Now, you must remember that it is necessary to strike up a meaningful conversation on your first date. It is equally important that your first date questions are not too personal, or recipes for boring debate. So, you should avoid asking questions about topics such as politics and religion on your first date.

So, what are the first date questions you should ask?

In this article, we have put together several questions that you could ask on a first date. To help break the ice and keep your conversation flowing.

The chances of a next date depend largely on the success of the first one. Therefore, you will find our tips for first date questions most helpful.

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Below are some of the best questions to ask on your first date:

1. What are you proud of?

The goal of a first date is to get a fair idea of your partner’s personality. It would be great if you allowed them to talk about themselves. What better way to get someone talking about themselves than asking them about their favorite moments?

Everyone has their biggest achievements and their proudest moments. They always feel comfortable talking about them whenever they get the chance.

Besides giving you a hint of their most cherished accomplishments, how they respond to this question could also give you provide you with a good assessment of their true personality.

2. What’s your most embarrassing moment?

Certainly, everyone has got bloopers. Ranging from an epic wardrobe fail or making a total joke of yourself in front of the class. We all have days that we would rather not remember.

While some feel comfortable recalling the incident and having a good laugh over it, others do not share the same feeling.

However, this question is the ideal ice-breaker and a great way to learn more about your partner’s character.

3. What places would you like to visit?

Whether it is the mystical Land of Oz or the next town, chances are that your partner has several destinations on their bucket list. So, why not ask about those on your first date?

And don’t just stop at knowing where these places might be. Also, ask questions that get your partner to open up about their interests in those locations. You might learn a thing or two.

This could help improve your knowledge of the world and its locations. Besides, asking this question could give you some useful ammo for springing up pleasant surprises in the long run.

4. What superpowers do you wish you have?

Although this question may appear a bit ridiculous for adult conversations. However, it is a great way to get your partner to open up about their favorite fantasies.

Everyone grew up watching superheroes do their thing on the silver screen, and wishing we were in their shoes. There’s no point denying it.

There’s no better way to lighten the mood and also share a good laugh than watching your partner describe possible scenarios of what they would do with their superpowers.

5. Would you rather… First Date Questions?

This never gets old. This type of question is great for triggering lengthy conversations.

Would you rather have a chocolate flavor or vanilla? Lakehouse or city flat? Rock concert or opera?

These first date questions are great for getting your date to talk about their hobbies and personal preferences.

6. What’s your favorite principle?

It’s hard to find anyone without a guiding principle. Let’s face it. We all have personal mantras that influence our lifestyle and condition our responses to even terrible circumstances. And we also feel comfortable telling others about these principles.

So, it’s cool to ask your date about their favorite mantra. Besides telling you what it is, chances are they would go on to tell you how they came about their guiding principles. And how it has worked wonders for them.

This is a great question for sustaining lengthy conversations. It also gives you ample opportunity to understand your partner’s attitude towards life.

7. What game would you beat anyone at?

Asking your date about their favorite games is also a great way to keep the conversation flowing. Even if they do not enjoy playing any games, you could easily learn about their hobbies and their favorite activities or interests.

8. What chores bore you the most?

House chores are boring. No jokes. And chances are that your date has chores that they resent. Go ahead and ask about it.

This question could get your partner to open up about the chores they would rather have someone else do. It also provides a good opening for sharing childhood memories.

9. What if… First Date Questions?

Just like the “would you rather…” questions, this type of question is open-ended as well. It allows you to fit in whatever scenarios you wish.

What if you won a million-dollar lottery? What if you could speak to your favorite superstar? What if you were 16 again?

These first date questions allow you to understand what your date would do in likely – or unlikely – scenarios. Remember, the aim is to keep the conversation flowing. So you can stick to highly unlikely scenarios that allow your date to unleash their imagination.


It’s easy to have the most rewarding first-date experience without any stress. Just use any of these first date questions we have shared to make your partner comfortable and keep the conversation flowing.

Although the questions we have listed are great for striking conversations on a first date, it is important that you pay attention to the responses you receive, and use them as leads for continuing your discussion.

Remember, there is no rigid principle to follow on a date. So, do not appear boring by sticking to an already prepared list of questions.

If you want to take your relationship further, endeavor to check out this post Dating With Purpose.