The Best Online Dating Questions and Icebreakers

Online Dating
October 20, 2021

Online dating is becoming one of the primary ways for people to connect.

In 2021, 30.4 million Americans are finding their dates through the online dating websites and apps. It’s clear that online dating has become an extremely popular way to find the types of relationships you’re looking for! 

Nowadays there are so many different online dating options to try that it’s easy for someone to either experiment with many platforms or find one that suits them best. 

But as normal as online dating is becoming, it can still be a pretty intimidating experience. 

And despite profiles and photos, there’s always the questioning of who is on the other end of the screen, whether they are who they say they are, and if you are going to really connect in-person. While you’ll never know for sure until you meet them, there are ways to find out more before committing to an in-person encounter. 

Of course, one of the benefits of online dating is that you can talk to someone before meeting them in person. Keeping an open and straightforward conversation can help you figure out if this is someone you can have fun with. It can be a great way to date safely and have overall better dates.

But, it all depends on the questions you’re asking before the first date! 

Here are our best online dating questions you can ask anytime!

Online Dating Icebreaker Questions

You might be asking yourself...What questions should I ask on a dating app?

One of the bigger complaints about initial online dating conversations is that people don’t enjoy the flat and tired greeting of “hey” or “hi”. 

Even worse is the waving emoji or GIF!

When figuring out how to greet a match, one of the most important keys to success is knowing what exactly you want to get out of the exchange. 

Are you looking for a fling or are you seeking someone to date long-term? Do you want the physical nature of the relationship to be the main focus or are you looking to take it slow? You don’t have to spell out just what exactly it is that you’re aiming to get, but knowing what you want will help your opening lines. 

The good news is that there’s really no wrong answer to how you approach someone online as long as you’re being respectful and honest about what you want. The bad news is that it’s not always going to align with everyone — which is unfortunately just part of the dating game. 

The better news is that a good icebreaker can be a great way to weed out bad matches and people who just aren’t on the same page as you. 

Try starting with a funny but tame joke! 

“Why do bartenders use blenders? To break the ice.”

Funny openers can be tricky — but if they land, you might get a date with someone who really gets you! 

If you do decide to go for the funny opener, consider making the punchline something silly, or maybe even some self-deprecating humor - but not the person you’re trying to strike up conversation with. What may be playful teasing may come across as rude when you can’t convey body language or tone. 

Another option is to compliment something in their photos or bios.

“The photo of you hiking is amazing — what a beautiful sunset! Do you hike often?” 

This is complimenting their photo but in a way that is not about their physical appearance.

If there is a solid universal approach to first online dating questions, it would have to be this. 

Find something interesting in their profile and incorporate it into the opening line. If it’s in their profile, chances are it’s something important to them that they’re proud of. 

“What are you looking for on [insert dating app name]?”

The direct opener can be a good method if you know exactly what you want.

It can be a relief to cut to the chase rather than go through a few rounds of stilted small talk before realizing you and your match are on different pages.

“Hey there! How’s your week going for you?” 

Worse comes to worse, this line may be a little generic but it’s still miles ahead of just saying “Hi”. It’s a friendly opener that doesn’t put on too much pressure but still invites them to open up. 

Other online dating icebreakers include: 

  • Asking their pet’s name if they have a dog, cat, or even a weird one like a lizard!
  • Asking their favorite restaurant if they talk about their love of food
  • Commenting about their music tastes (if they feature something like Spotify on their profiles!)
  • Asking about one of the prompts in their profiles (like “best travel story” or “never have I ever…”) 
  • Talking about their Instagram photos if they’ve connected that to their profile


We wouldn’t be doing our job if we didn’t say what online dating icebreakers to NOT use! 

  • Don’t compliment their physical appearance - this can be off putting and show that you only care about looks
  • Don’t ask about their job/what they do for a living - that’s just BORING! (unless it seems like a really cool job and you’re genuinely interested in it!)
  • Don’t ask about other people in their photos - also you should NEVER include other people in your online dating profile photos for safety reasons. Asking about other people shows you’re more interested in them than the person you’re trying to talk to!


How do you keep a conversation going with online dating?


It happens to everyone - you’ve sent a great opening line, they seem interested, and the two of you are having a great conversation!

Then, out of nowhere, they don’t reply. 

The first assumption you could make is that they’re not interested anymore — but considering that online dating is so different from going to a bar and talking to someone in front of you, chances are they just got distracted by real life. 

There are ways to draw them back in without ruining the good vibes or seeming a little desperate!

“Something really funny and weird happened on the way to work today...”

By offering a story to tell, you’re not only showing a piece of your life to them but also what your sense of humor is like. Plus, it’s a really organic way to get them to re-invest in the conversation. 

“Have you seen [this movie]? I just saw it for the first time and it was so good!” 

By sharing your excitement for something you enjoyed, you can bring a positive vibe to their inbox. Movies and TV shows are great conversation fodder because pretty much everyone has opinions about them. 

“I just tried [something new]!” 

This sort of line is great because not only does it show that you are open to trying new things but also invites them to share their opinion. Plus, depending on what it is, you can show them the result! 

But, don’t lie. You should have actually tried something new that you can potentially explore with this person.

“The sunset is so gorgeous right now, I wish my camera could do it justice.” 

More positive vibes. Some people, whether they’re new to the game or have been through the ringer a few times, tend to associate online dating messages as a chore before the actual date. By messaging nice things that are unrelated to dating, you’re also reminding them that meeting new people can be really fun.  

“So [subject we were previously talking about has an update!]” 

If you guys both previously expressed interest in something, mentioning it again is a great way to bring them back into the conversation. A common interest is a great way to make connections. By geeking out together over something, you start the relationship with excitement and fun. 

Now, let’s look at some examples of quality questions to ask different genders (okay, okay, we’re not into stereotyping genders, but this is a popular Google search that we want to help answer!).

Best Online Dating Questions to Ask Her

“What’s your favorite spot [for X] in town?” 

This is a great question to ask because it shows interest in her opinion as well as let’s you know what her ideal night out looks like. It might even lead to her sharing an anecdote!

This should be used a bit further into the conversation rather than as an online dating icebreaker. It could put off the wrong vibe that you’re trying to know where she frequents at first. 

But, it’s a great way to follow up with “Well, can I take you there sometime?”.

“What is your idea of a perfect date?” 

By asking her this, you’re allowing her to set the context for a night out. It’s letting her know that you care more about what she wants than a prescribed idea of what a date should look like. 

Again, maybe not a good opener, but once you’ve both committed to a conversation, it can be a good way to take the next step.

“What’s your love language?”

Asking her how she likes to share affection - and also sharing what works for you - is a great way to get to know how this other person gives and receives love. It can be a great way to get a sense of her boundaries ahead of time - it’s good to know if she’s not into romantic gestures, for example, when you go on a date. 

“What do you like most about your job?” 

Alright, alright. I know we said DON’T ask about the other person’s job — but that was as an icebreaker question. It’s okay if you ask further on into the conversation. This is also a more interesting way to phrase the question than “what do you do for a living?”.

If you ask about her career, you show that you’re paying attention to the whole picture. You’re acknowledging that you’re interested in her individual life and what her aspirations are. 

Alternatively, if she actually doesn’t like her job, you can provide an opportunity for her to vent about something - which is a bonding experience for a lot of people. 

Best Online Dating Questions to Ask Him

“What is something that you’re really great at doing?” 

This can be an opportunity for him to show something that he’s proud of. It might be career related or hobby related, and you could end up finding out something really interesting about him that isn’t on his profile. 

“What makes you laugh?” 

What makes him laugh can help show you whether or not you have chemistry and what his sense of humor is like. It shows him that you want to know more about him and what he enjoys most about spending time with people. 

“What are you looking for on this app?” 

You may not want to kick off the conversation with this question, but it’s a good idea to ask it at some point for anyone to make sure that you two are on the same page when it comes to dating and save you both a headache later down the road. 

“What was your favorite movie/book/sport as a child?” 

We typically want to know what our partner was like as a child, but it can be a hard question to answer sometimes. By asking a specific question about what they liked to do as a kid, we can help them feel less on-the-spot and allow them to paint a picture without using vague adjectives. 

Online Dating Questions to Ask Before the First Meeting


Now for the next step - asking them to meet in person! Before springing the big question on them, it helps if you gauge their feelings with questions like the following:

“Would you like to connect further — maybe over the phone or in-person?” 

This is a little straightforward but can help deflate any tension in the conversation if they like you but, for any reason, you’re not sure where you stand. It can also help them open up about what is holding them back, rather than them keeping those feelings bottled up. 

“What’s your ideal first meeting?”

By asking them to describe what they want to have, it not only helps describe what they are like as a partner but if they would prefer a virtual date first, it would be a good opportunity for them to say so. It also can help you plan what kind of a fun night you could have! 

Rather than saying “what’s your ideal first date”, saying “meeting” lessens the pressure as well!

“What’s your opinion on [topic]?”

If you have strong beliefs about certain topics, knowing upfront how another person views them can be important to understanding if continuing the conversation is worth your time. 

“What’s your typical Saturday night look like?”

Understanding how someone spends their weekends can be a big indicator of who they are. If you’re looking to party, someone who says they love going out is perfect! But, if you’re looking for someone who likes to stay in and watch movies, this might be a deal breaker!

“What do you like most about our conversations?”

Their answer will show a lot about how they think about you! If they say something about your appearance they did not understand the question at all - what a fail! If they say something generic like “they make me happy” or “you seem interesting” they’re either lying or just boring as hell. It should be something deep like your aligned interests or how you’re passionate about something!

“What are your friends like?”

Understanding who someone hangs out with is a good representation of who they really are and what they like in other people. If they don’t have any friends, that can be a major red flag!

“Are you close to your family?”

Everyone’s family dynamics are different. But, if they start talking sh!t about their family, this can also be a major red flag! Save the family drama for a later time, not before the first date!

“Where do you see yourself in five years?”

This question can help you understand their personal, relationship, and work goals. If they say something like “I’m just taking it day by day” - this could be a turn off - unless you’re also YOLO’ing. If you’re looking for something more committed, like having a family in that timeframe, it will reveal potential long-term alignment!

Questions for When You’re On the First Date

Ok, it’s happening. You’re going on an in-person date. 

Now for the hard part...What are you going to talk about? Here are some ideas that are way more engaging than simply saying “tell me about yourself”!

“What’s something that you want to learn how to do?” 

This is the sort of thing that most of us don’t get to talk about in our everyday lives and is a great way to get to know another aspect of them. Plus, who knows, depending on what it is, maybe you guys can go to a class together.

“What’s your ‘happy place’?” 

This can be a literal place, like a vacation spot or a favorite bar, or it can be a state of being, like enjoying a Sunday morning off. It’s an intimate question without asking for anything too private. 

“What was your first concert?”

By asking a specific question like this, you might be able to open them up to sharing a story that they find fun. Any question that gives them an opportunity to tell a story is usually appreciated! 

“Where did you go to school? Did you have a favorite class?” 

This sort of question works better during in-person dates because it feels less like an interrogation of their credentials and more like a chance for them to tell you their life’s story, more or less. It might also hint at what their plans are for the future. 

“Do you think you would enjoy being famous?”

Asking them a fun hypothetical question is a fun way for them to tell you who they are in a new and interesting way rather than the usual run-down. 

“Is there anything that you think shouldn’t be joked about ever?” 

This is a great way to gauge not only what a daily conversation with them would be like, but also how aware they are or are not about privilege, politics, and traumatic life experiences. 

“What in your life are you most grateful for?”

This is a positive question that will let them show you what their priorities are like as well as who is in their life. Their answer may surprise you and let you see a different side of themselves. 

You’ve got all the online dating questions you need to succeed!

Now that you're armed with good online dating icebreaker questions, how to keep the conversation going when online dating, and questions to ask before the first in-person meeting, you're ready to take the online dating world by storm.

Of course, remember the most important thing when meeting someone that you met online is being safe!

Safety practices can include meeting in a public place, picking an off-day like a Tuesday, letting your friends know ahead of time when and where you’re going, having a safe word to text friends to give you a ring to escape the situation if it’s going downhill, and choosing to meet people through more popular apps that have identity verification. 

Have fun!


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