Best Online Dating Questions: Fun Conversation Starters

Mastering Online Dating Conversations: Top Questions to Ask

You sign up on a dating app, you fill in the bio, you match with a few gorgeous people. Next comes the horrible revelation – you need to talk about something with these people, and you have no idea what to say.

Don’t fear! The Once team is at your rescue. Today, we’re going to talk about the best questions to ask on a dating app, share examples, and help you master the art of online dating conversations.

Essential Online Dating Questions to Spark Interest

First things first, let’s start with the basic, absolutely essential internet dating questions to ask someone you fancy.

There are several categories of online dating questions that you want to cover to ensure you guys are a good match.

Hobbies and interests. Asking someone about their favorite things to do on weekends and in their free time is an ever-green dating question. It is a bit cliche, but those exist for a reason. Many people tie their identity to their work, but there is so much more to every human being out there. Knowing what they’re fond of outside of their careers helps you get a more complete portrait of them as a person. For example, ask them if they’ve picked up any new hobbies recently, or if there’s something they always wanted to try but didn’t get a chance yet.
Food and beverages. Drinks and food are two of the most enjoyable things in life. Who doesn’t like a good meal and a delicious beverage along with it? Ask them what their comfort food is or something unique they’ve tried recently. If you’re in the same city, it’s a good idea to fish for their recommendations on cafes and restaurants. Also, some people ask the what-would-be-your-deathrow-meal question, but it’s too dark for our taste and can creep someone out.
Traveling. Weirdly, how people like to travel and the destinations they pick tell a whole lot more about them than many other things and even their actions. Here you can ask your match about their bucket-list destinations, favorite spots, and absolute no-nos. In fact, finding out the places someone hated and the reasons for that is very eye-opening.
Aspirations. Not everyone needs to have those grand, impossible dreams, but everyone has aspirations of some sort. Asking about such personal things can seem nosey, and sometimes it will be perceived like this, especially if you’re not on the same page with the person in terms of vibes. However, if you’re not rude or aggressive about it, most people will be eager to share what they’re thinking and dreaming about. If you’re nervous about asking this, you can start by sharing your own aspirations first. For example, “I always wanted to buy a farm and build a shelter for dogs and name it in honor of my childhood pet. What about you?” People will be more relaxed and eager to open up if they see you’re not afraid to be vulnerable yourself.
Work. It’s a bit of a weird topic to ask about right away because some people really hate their jobs and are super burnt out. On the one hand, they might want to share crazy stories and feelings about their workplaces. On the other hand, this can be a painful topic to discuss. Still, for the most part, you’ll be fine asking people about their occupation. The only trick here is to ask something that doesn’t look like a copy-pasted question from a how-to-date book. For instance, instead of asking if they like their job, ask what they find the most fulfilling and dreadful part of their current role.

If money wasn’t an issue…

Finances define our lives greatly. Those of us who weren’t blessed with a trust fund have to spend a significant amount of time earning a living.

Fair to say, if money wasn’t on our list of concerns, our average days would look very different. So, consider this as the final boss of essential online dating questions and ask your match what they’d be doing with their lives if money wasn’t an issue.

It’s a good idea to think about it yourself too. Not just to be able to share your own response quickly but to help yourself understand where your passions truly lie. For instance, would you be lazing around all day, traveling the world, applying to universities, or clubbing like there is no tomorrow? It’s an interesting exercise for both of you.

Don’t turn the dating chat into an interrogation

Your conversation needs to flow naturally. There is no rush to go through all categories right this time. If you click, you’ll have plenty of time to chat more and fill in the gaps. Focus not on the quantity of the questions asked, but rather the outcome.

Have these questions you asked helped you understand the other person better?
Were you able to find common ground with them?

It’s vital for you to see if you want to continue the relationship at this point, so instead of rushing through 20 questions in one sitting, focus on a few and explore them deeper. If you end up going through the whole list, that would be marvelous! If not, don’t worry, there’s still time.

If you push them too hard while trying to get to know them, you’ll risk looking weird and invasive.

How do you spark deeper conversations with the right questions?

Fun questions are important and light-hearted conversations are paramount to getting to know each other and checking if you like one another.

However, you need to go deep at some point if you want to create a genuine, solid connection with the match.

Deep conversations start with open-ended questions. As banal as that, you need to ask someone proper questions to get the answers you’re looking for. Don’t go as broad as “Tell me about yourself”, but avoid overly narrow questions, such as “Do you like pizza?”.

Another trick to get longer, more detailed answers is to ask the other person about their passions. If somebody is obsessed with cinema, they’ll be happy to chat about it 24/7. If you look at the person’s dating app bio, they most likely will have something hinting at their hobbies, interests, and areas of expertise.

Also, the way you respond matters. You can ask the best online dating questions in the world. Yet, if you don’t pay attention to the answers and don’t follow up with more questions, then it all goes to waste. Be an active listener, respond thoughtfully, and engage with their responses properly.

Lastly, try to have a balanced conversation. If someone is talking or messaging 80% of the time and the other person is only doing 20%, then something’s off. It’s hard to orchestrate an ideal chat, but try to build an environment where you’re both eager to speak up, so you both share approximately the same amounts of information.

Tailored Questions for Specific Scenarios

Now that we’ve covered the essentials, let’s move on to more specific and tailored questions to ask online dating matches.

Good icebreaker questions for online dating

Everyone likes a good dating icebreaker. It eliminates the tension, helps you ease up into the conversation, and kick start the chat with something positive.

Here are some examples to get you inspired.

What is something that makes your day instantly better, no matter where you are and what you’re doing?
What is your proudest moment in life?
What is the best advice you’ve ever received?
What is the best advice you’ve ever given?
If you could be any animal for a day, what would you pick?
Window or aisle seat on the plane?
What’s your drink of choice at 7 am in the airport?
Do you have any secret talents?

Questions to ask guys online

We’re fans of universal online dating questions that work for both sexes and, for the most part, all questions can be addressed to both men and women.

Still, sometimes it’s nice to lean into the sex-specific things or dive into what you, as a woman, would need to learn about a man before you start dating him.

What is the one moment of your life you’d like to relive?
What is your hobby outside of work?
What is something that you like doing around the house?
Why are so many men obsessed with watching sports?
If paternity leave was possible, would you take it?

Questions to ask a woman in online dating

We’ve shared examples of questions for men, so it’s only fair we share some great online dating questions to ask the women you like.

What’s one book that you keep coming back to?
How would you plan your perfect weekend?
What do you think I would be surprised to learn about you?
If we had the same salaries across all jobs, which career path would you pick?
Would you like to be a mentor to someone one day?

Crafting the Perfect Opening Question on a Dating App

The best questions to ask on online dating aren’t always spontaneous.

Sometimes, a little planning helps craft your opening message to perfection. Here are a few tips to master the art of first questions on the dating app.

Make your opening question:

Personal
Engaging
Easy to respond to
Friendly

Ask them about the photos of information in the dating profile, be positive with the way you phrase them, and don’t go into too personal topics as your opening line because people will be hesitant to respond.

Your best bet is to follow up on something mentioned in the profile. For instance, if a guy says he’s an avid cook, ask what the most complicated dish he’s prepared yet is. Or if you see someone mentioning their passion for tennis, ask if they have a favorite player and if they’ve ever had a chance to see them play.

You can ask flirty questions too, by all means, but be prepared that you’ll be perceived not as a potential long-term partner but rather as a hookup or a quick romance.

Recognizing and Responding to Red Flags in Online Conversations

Red flags and inappropriate behavior are a problem in dating overall, but online dating specifically. People feel more relaxed and safe when they’re typing away in their homes miles and miles away from the people they’re speaking to. That’s why sometimes you’ll get the wildest texts and instantly understand that this person is a huge No.

Unfortunately, not everyone is so forthcoming with their downsides and they manage to hide red flags well. If you add your infatuation with the person to the mix, it becomes twice as hard to spot anything bad about them.

Here are the common red flags and signs that something isn’t quite right.

They’re inconsistent with how much they text you and the tone of their texts.
Their story is inconsistent too. For example, they said they’re an investment banker but they don’t know what derivatives are.
They’re pushing for intimacy when it’s clearly too early for that.
You can’t get them to have a call or a video chat with you.
They’re asking you for too much personal information and demand details too.
They’re asking for money.

How do you deal with red flags? There are a few key strategies:

Block them and move on. You don’t owe anybody your time or attention. If something seems off, block and move on.
Report and block. If you think that the person can be threatening to other users of the dating app, you can report them first to ensure their profile gets deactivated.
Wait and see before taking action. If nothing terrible happens and you’re not 100% sure that the red flag is real, you can wait and monitor the situation for a while.
Address the elephant in the room. If you like this person but their behavior is bothering you – ask them directly. There’s no harm in clearing the air. If you mention your concerns and they belittle or ridicule you, then great – you’ve just dodged a bullet! And if they’re ready to have a talk and explain what’s going on – even better. With texting it’s easy to misinterpret what the person is trying to say, so it’s a good idea to double-check something weird first before taking radical action.

The bottom line is that you shouldn’t tolerate worrying signs. Online dating opens up access to so many people around the world, that it makes no sense to stick to someone who is not a good match and might mistreat you too.