Questions to Ask on a Dating App

Dating 101
30 Oct 2023
10 min read
31 Great Questions to Ask on a Dating App

Wondering how to meet anybody with your busy schedule? A working solution is to install a dating app and reach singles nearby in the comfort of your home. But how to start a conversation to actually get a date there? Some dating apps (including Hily) will offer several conversation starters to assist you here, but this may not always work. That’s why you need your personalized set of questions to ask on a dating app, and here are some working examples that can enhance your dating experience.

Know Your Online Dating Goals

What are the best online dating questions? That depends on what you are trying to accomplish and the type of person you want to attract:

  • Short-term: If you want to take things slowly or just keep it very casual, strike up a fun conversation with interesting questions that don’t dig too deep.
  • Long-term: If you want to engage in meaningful conversation while ensuring you and the person you’re with have similar views on in-depth issues, you can ask some deep questions. Yes, that may put some people off, but they probably weren’t your type to begin with.
Tips on how to use our questions to ask on a dating app

5 Tips for Asking Questions on Dating Apps

So, what questions to ask, and when should you ask them? Before you start using any of the questions below, keep in mind these tips:

  • Read the room: Don’t ruin a moment with a poorly timed question. The best words are always context-based.
  • Get a feel for their personality: Some people are more guarded than others, so you should feel whom you are talking to for the best effect.
  • Be fair: Don’t ask personal questions you wouldn’t answer yourself. Honesty is the key to long-standing and healthy relationships, so be ready for that.
  • Rely on yes/no questions: Thee are simpler to answer – thus, you’re more likely to actually get a reply with them. But be ready with a follow-up as a great ice breaker.
  • Slow Down: Don’t be in a rush. This is a conversation, not an interrogation – and the more you push, the less likely you are to actually a get.

Related reading: How to Flirt With a Girl – And Get a Date!

31 Great Questions to Ask on a Dating App

Online dating is amazing, but it doesn’t get you out of those awkward first conversations. You need some help. Surely, you aren’t going to talk about the weather. You need questions to ask that will spark some fabulous conversation. So, where do you begin? Keep reading for some intriguing questions to ensure you leave a good first impression.

1. What Was Your Most Embarrassing Moment in High School?

Sure, there’s always some risk when you ask another person to share an embarrassing story. It could end up being gross or trauma-dumping. Still, most people will pull out a slightly funny, relatable story.

Just be prepared for a bit of turnabout. There’s no way you’re getting out of this conversation without spilling your own story about your biggest, most embarrassing thing.

2. Do You See a Serious Relationship in Your Future?

This one certainly gets down to it, but it may not be a deal breaker. The future could mean tomorrow, or you could be referring to their five-year plan. Ask this question if you want to start a conversation about their intentions without coming on too strong.

3. What’s Your Go-To Karaoke Song?

This is a fun first-date question to ask. It’s light and conversational. Most people will be perfectly comfortable sharing what they sing on karaoke night or confessing that they are a karaoke version. This is a great question for keeping the conversation going and may just give you ideas for date number two.

Related reading: Should You Kiss on the First Date?

4. Do You Have a Hidden Talent?

Are you looking for some funny questions to ask that will keep things casual? This is a great online dating question. It’s interesting to learn what a person’s hidden talent is.

Perhaps they can do card tricks, sing the alphabet backward, or do an impressive front flip. You can have some interesting conversations during an online date or in person if you lead off with this question.

5. What Did You Learn From Your Last Relationship?

Now, we’re getting into some deeper topics. That’s fine as long as they feel comfortable sharing their answer with you.

Just be self-aware before you ask this question. Otherwise, you might create an uncomfortable situation from what you thought was a simple question. If you don’t mind answering, you can learn quite a bit about their past relationships and better understand where they are.

Related reading: Ex Still Renting Space in Your Head? 11 Tools to Break Free

6. Name Your Biggest Pet Peeve That’s Also Very Unreasonable

What’s an unreasonable pet peeve? It’s something that you hate but are also aware is a bit ridiculous. It’s a fun question that may hit better than asking the other person to share an embarrassing story.

There’s another great reason to ask this question. It reveals something about the other person’s personality. If they answer, it shows they have the insight to recognize when they are being silly about something. Someone who thinks none of their pet peeves are ridiculous may take themselves too seriously.

7. Are You a Cat Person or a Dog Person?

“Dogs kind of default to making friends unless provoked. Cats seem to default to making enemies unless convinced otherwise.”

Perry Elisabeth Kirkpatrick, a Christian author

This isn’t the most interesting question. Still, if pets are important to you, it is useful.

This question could count quite a bit towards measuring your potential compatibility. Besides, this is the gateway question both of you need to share those adorable pet photos.

Date based on compatibility
Use Compatibility Quiz on Hily to check if you have similar or complimentary traits before you start dating
Try Hily here

8. What’s Are the Top 3 Items on Your Bucket List?

The whole bucket list comment may seem rather trite and played out, but give it a chance. You can learn a lot about a person.

Someone’s bucket list reveals how adventurous they are, the relationships they cherish, and the dreams at the top of their priority list. That’s a lot of valuable, real-life information if you are searching for the ideal partner.

9. What’s the Most Embarrassing Nickname Your Family Called You?

If you want to get to know somebody, get them talking about their family. This question is perfect for that as it approaches the subject light-heartedly.

This question allows them to tell a funny story or start talking about their family if that’s okay with them. If not, they can just brush it off and move on to the next question. In that case, be prepared that they may have a dicey relationship with their kin.

10. What Would Make You Walk Out of a Job Interview?

This is a great way to start a good conversation about something relevant to many of us right now. If you’d like to get a conversation going on this, start with this question.

You can develop the conversation into a deeper discussion on the work environment, fair pay, remote work, and unions.

You might find out that the person you are dating is passionate about advocacy and organization. Then again, you may just find out that the lack of a cappuccino machine in the lounge is an absolute deal breaker for them. In any case, it’s a great question.

11. Imagine That Money Is No Object. What Is Your Dream Job?

When you ask your date about their passion, they may stumble. But their ideal job is different.

This question narrows things down; what they share can spark a neat convo. Of course, you should also be prepared if they have a similar question to ask you.

12. What City Would You Choose For the Perfect Date?

Knowing your partner’s ideal city date can tell you a lot about the way that they grew up. Many people feel most comfortable in places that connect them with nostalgia:

  • Growing up in the country may make a romantic little town a dream destination for a date
  • Someone who grew up in the city may wish to visit a place that is very loud and bright

By asking them this question, you can get a bit of a look into the type of environment they grew up in, and in return, you also get to see if the two of you would be a good match.

Surprise them with creative questions for an online dating app

13. Are Your Family Dynamics Closer to Rick And Morty or Little House on The Prairie?

Although the members of both of these families really do care about each other, the dynamics of these families are just about the same as an apple and a television set:

  • The family in the Little House on the Prairie series often shows how much they care for each other. They help and take care of the home and community in a way that makes everyone feel good about supporting them.
  • The Smith family on Rick and Morty leaves less to be desired for some. Although they obviously care about each other, with the constant fighting and insults, it can be difficult at times to fully grasp their connection.

As you can see, you can dig deep with this fun question – or get a new answer that will surprise you!

14. Your Crazy Rich Aunt Leaves You a Million Dollars: What Do You Do?

This question can help you determine if someone is good with financial decisions. After all, even though a million is a lot of money, it can disappear pretty quickly if you aren’t smart about your spending, and sometimes it can disappear quickly even if you are smart about it.

You can learn so much about them with this question:

  • Are they the type of person to put it away somewhere safe with the hope that they will be able to let it grow for future use?
  • Will they immediately pay off their debts and then do something with the remainder?
  • Are they going to forego all forms of advice and start spending immediately?

These are only a few examples of the impressions you may get from this question, but each one tells of their ability to plan out their finances. This is important if financial compatibility is a dealbreaker for you.

15. Have You Ever Been the Cause of Another Person’s Worst Date?

This question can potentially lead to a good story or a terrifying revelation. But the question itself can enter two potential answer groups. Were they deliberately causing the date to be bad, or was it just an unfortunate mistake?

16. Who Is Your Long-Lasting Celebrity Crush?

The answer to this question can give you an idea of their ideal partner. Or at the very least, the type of person their ideal partner might be.

Are they the type to have had a crush on Nikki Minaj? How about Keanu Reaves? Both are very well-liked performers who attract different kinds of people.

17. What Happens on Your Perfect Sunday Morning?

“Do not let Sunday be taken from you. If your soul has no Sunday, it becomes an orphan.”

Albert Schweitzer, Alsatian polymath

Every person has a different idea of a perfect morning, and how they answer this question will let you know what they are like. They may be the relaxed type who wakes up and immediately starts to read a book or pet their cat. They may also be the go-getter who will stop at nothing to wake up early and get the ball rolling, even on a lazy day such as Sunday.

For many people, Sunday morning is the only time that they truly get to themselves. By asking them this question, you get a better idea of what their ideal type of life might be. As well as what they may be looking for in a long-term relationship.

18. If You Could Have One Superpower For an Hour – What Would it Be?

This question might seem fun, but it can actually point out their hidden talents:

  • Wishing to fly often comes from a person who is well-read about the world and wants to experience it easily.
  • A person who wishes to read minds may already understand people very well.

This is definitely one of those dating questions that you can ask to better understand what they are good at and what they enjoy.

19. What Is Your Guilty Pleasure TV Show?

People love to talk about their favorite shows. This is a great icebreaker question on dating apps for this reason alone. It’s also a great jumping-off question for planning to binge-watch shows together or compare notes on your latest TV obsessions.

20. You Must Give an In-Depth Lecture With No Time to Prep: What’s Your Topic?

It’s always a good idea to ask a few questions about the other person’s interests and passions. This question allows you to do that but frames it in an interesting way. Essentially, you are giving them space to talk about their favorite topic. That’s sure to keep things going in a positive direction.

21. What’s Your Favorite Restaurant for a Cheap Meal?

This is one of those funny questions that can give you a really good look at the type of life they are accustomed to. Many areas and classes have a different idea of what it means to be cheap and how to get the most value for your money.

If they state that their favorite place for cheap food is Popeyes or McDonald’s, they most likely grew up in the inner city or a rougher area of town. But they most likely grew up in the middle class if they give a local restaurant.

Related reading: The Great Outdoors – 27 Date Ideas in the Open Air

22. What’s the Craziest Thing You Ever Did for Love?

Ideally, this will be a fun and flirty question. They’ll share some romantic tale of a big gesture they made to save a relationship or express how much they loved somebody. Hopefully, it won’t involve anything illegal, stalkerish, or creepy. Then again, it’s probably good to find that out now!

23. What’s The Best Compliment You Ever Got From a…

Fill in the blanks! The best compliment could be from a lover, parent, boss, teacher, or somebody else. This question can brighten up a conversation and help you get to know somebody through their real-life relationships.

24. What Is Your Favorite Cuisine?

People are passionate about food. That’s why this is almost always a fun topic of conversation. Food plays such a significant role in life events, family, and culture. Most people just love talking about it. This simple question can lead to discussions about parties, restaurants, travel, or just swapping recipes. What a great way to gain insight into their life and world views.

Ask about love languages if you want a serious relationship

25. How Do You Feel About The Whole Love Language Thing?

People tend to run hot and cold on the topic of love languages. Some people think it’s the silliest thing ever. Others see it as hyper-religious dogma that puts the responsibility of communication in a relationship entirely on the woman. Then, there are those who truly believe it is a vital life tool to help couples understand one another and ensure things work out even if they aren’t a perfect match.

26. What’s Your Best Quality? Worst Quality?

It’s good to balance flirty questions with some challenging ones. This asks your date to look deeper and provide insights about themselves. Hopefully, you wouldn’t ask this question without being prepared to answer it.

27. If You Could Learn a New Skill For Free, What Would It Be?

You want to learn how to crochet. Maybe they do too! What if the two of you could find something to learn together?

When you ask this kind of question on dating apps, you can connect with people interested in learning the same things you are. That makes planning the second date easier.

Related reading: Out with the Cliché Second Date Ideas

28. How Often Do You Talk to Your Closest Friend?

If things get serious, their best friend will be a part of your social circle. That’s just how it is.

Be honest. You’ll talk to your best friend about this emerging relationship too. So, it’s good to get an idea of just how close they are to their bestie.

29. What Universally Popular Food Item Absolutely Disgusts You?

This is another fun conversation starter. It’s a silly mood booster that keeps the convo going.

As an alternative, consider a would you rather question. These offer silly or absurd choices between objects or activities.

Would you rather eat the food you hate the most for dinner or watch the worst movie in the world on repeat for 12 hours?

30. Tell Me About Your Typical Day?

This is when you want to learn more about the other person’s life. Isn’t this the perfect question for doing just that?

31. What’s the Precious Thing You Own Worth Less Than 50 Dollars?

What are they sentimental about? People don’t always want to speak about things that are pricey. It seems too much like bragging. However, they love to discuss items that are precious to them and make life just a bit more joyful.

What to Avoid and Why Icebreaker Questions Are So Important on Dating Apps

Two of the biggest challenges of online dating are learning about the other person’s life and personality. You are just beginning to start a relationship with them or determining whether there is potential for a relationship. Use these questions to help that process along.

But be careful about questions that might bring up bad memories or spark discussions you aren’t ready to have. For example, bringing up past relationships might trigger sadness, anger, or regret. That’s probably not the mood you are looking to create. So, avoid a question that asks them what caused their previous relationship to end

Dating Tips Author
Shelly Standford
After a devastating relationship breakup, I threw myself into the dating scene by registering on Hily. I had over 100 dates - some absolute disasters, some pretty average, and some that were actually great. So many stories to tell and insights to share with you guys!

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