Updated on October 3, 2022

20 Best Conversation Starters for Online Dating

When it comes to online dating, the first impression is key. If you want to make a good first impression, you need to have an interesting conversation with your potential date.

This can be tricky, especially if you don't know what to talk about. You don't need a dating coach or listen to dating experts for hours on end. Being yourself and opening with some great conversation starters is what will get the momentum going.

Here are 20 questions you can ask when finding someone you'd like to talk to while browsing on dating apps or dating sites.

1. Ask Open-Ended Questions

Open-ended questions allow people to talk freely about themselves. They give people the opportunity to express their thoughts without being judged.

Open-ended questions are great because they encourage people to tell you more about themselves.

For example, you could ask something along the lines of, “What are your favorite hobbies?” or “How did you decide to become a doctor?” These types of questions provide insight into the person behind the profile.

2. Avoid Leading Questions

Leading questions are questions where the answer is already known to the speaker. Instead of asking, “Do you enjoy traveling?,” try asking, “Where do you plan to travel next?”

This type of question gives the impression that you already know what the person wants to discuss. Leading questions are generally considered rude and unprofessional.

3. Get Clues From Their Profile

If you want to know more about someone, take a closer look at their profile. There could be clues there that tell you something interesting about them.

For example, did they list their favorite movie or TV show? What does it say about them? Do they like sports or music? Maybe they’re into photography or cooking. You never know what you’ll discover when you dig deeper.

Look at their pictures. Do they have any pets? What kind of activities are they doing in their pictures? Did they visit a place you recognize? All of these can be great conversation starters and you might even find some common ground before even talking to them.

4. Give Them a Compliment

People love compliments and if you find something you like about their profile, let them know! Just make sure it’s genuine and specific.

For example, don’t say “you’re pretty” or “I like your smile.” Instead try something like, “Your eyes are so captivating” or “I love your style of dress.”

Compliments show that you are interested in the person and you are paying attention to detail.

5. Use Humor

Using humor gets people's attention. As an opening conversation starter online, it can be a great way to break the ice. But, you need to make sure that your humor is appropriate and not offensive.

Telling a funny story or making a witty observation can be a great way to start a conversation. Just make sure you don’t come across as mean-spirited or arrogant.

6. Ask for Their Advice

Asking someone for advice on a dating site might seem strange, especially since you have never met them before. However, it’s a great way to start a conversation and get to know someone.

People love giving advice, especially when it comes to something they are passionate about. For example, look at their profile pictures and identify if they have any hobbies or interests. If you see a dog in one of the pictures that could be theirs, then you could ask them something like, “I’ve been thinking about getting a dog. Do you have any advice on what kind of breed would be best for me?”

7. Discuss Current Events

Current events are great conversation starters because they give you something to talk about that is relevant and interesting. You can find out what someone’s thoughts are on current events, their views on the world, and their opinion on politics.

Just be sure to avoid hot-button topics that might be controversial or make the other person uncomfortable. Stick to something that is light and easy to talk about. To keep the mood positive, don't bring up any catastrophes or bad news.

8. Ask a Deep Question

A deep question is one that requires a response that goes beyond the surface level. It forces the person to think about their answer and gives you a better idea of who they are.

  • Some examples of deep questions include:
  • What is your definition of happiness?
  • How do you define success?
  • What is the most significant event from your childhood?
  • What are your thoughts on religion or spirituality?
  • Do you have any fears or phobias?
  • What motivates you in life?

Asking a deep question right off the bat might not be the best idea. You want to ease into it so that the other person doesn’t feel like they are being interrogated. Try starting with some small talk first, then transition into asking a deeper question once you get to know each other.

9. Ask What They Are Looking For

Without sounding too forward, you can just ask what they are looking for on the dating site. This is a great way to find out if they are looking for something serious or just something casual.

It also allows you to get an idea of what they want in a relationship and what they are looking for in a partner. If they are looking for a long-term relationship or something serious, then you know that you might need to take things slow. But, if they are just looking for something casual, then you can be more relaxed about the whole process.

Keep in mind that many people explicitly say what they are looking for in their dating profile already, so asking them this question might annoy them. It's also a question that many men ask at first, so keep that in mind.

10. What Do You Like About Living in (City)?

Most dating apps and sites will allow users to list the city they live in. If you are able to get this info, use it as a conversation starter. Ask them what they like best about living in their city.

This is a great way to learn more about the person and get to know them on a deeper level. It also allows you to find out if they are looking to move to another city or if they are happy with where they are.

If you live in the same city, you can also use this as an opportunity to make plans to meet up. You can suggest grabbing coffee or going for a walk in one of your favorite parks.

11. How Did You Spend Your Day?

This is an effective way to start a conversation with someone without them knowing it, especially if you're interested in learning more about them. You'll find out how they spent their day, what they like doing, where they live, etc.

People like talking about themselves, so asking about their day is a great way to get them talking. It’s also a low-pressure question that doesn’t require a lot of thought.

The downside to this question is that it can be very easy for the other person to just give a one-word answer and move on. If you want to keep the conversation going, you might need to ask follow-up questions.

12. What Are Some of Your Favorite Things to Do?

This is another great question that allows you to find out more about the other person. You can learn about their hobbies, interests, and what they like to do in their free time.

This question also gives you an opportunity to bond over shared interests and experiences.

13. How Do You Relieve Stress?

Since we all feel stress at times, this is a relatable question that can help you get to know the other person on a more personal level. It also allows you to find out how they cope with stress and what their triggers are.

This question can lead to some interesting conversations about mental health, self-care, and ways to deal with stress.

14. What’s Your Sign?

Ok, this is probably the most used "one-liner" in dating history. But, it can be effective especially if the other person is really into astrology. In fact, some people will only date others who are compatible with their sign.

But, if the other person is not into astrology, this question might fall flat. So, it could be a bit risky to ask this one. But, if you're feeling bold, go for it!

Some people will actually list their sign in their online dating profile. What you can do is check for sign compatibility. If you're a match, you could lead with that.

15. Do You Have Any Pets?

This question is a great way to find out if they are an animal lover or not. It's also a fun question that can lead to some interesting conversations about their pets, why they got them, what kind of pets they would like in the future, etc.

Do they prefer dogs or cats? Or maybe they don't like animals at all? This question can help you gauge their level of interest in animals.

16. Do You Like to Travel?

This is a great question for finding out more about the other person's interests. Do they enjoy traveling or are they more of a homebody? What kind of places do they like to travel to? Do they prefer adventure or relaxation?

This question can also lead to some fun conversations about your own travel experiences. You can bond over the places you've been and the places you want to go.

17. What's Your FavoriteFood / Movie / TV Show

Everyone has a favorite food, so this is a great question to ask. It's also a great way to find out if you have any shared interests when it comes to food.

For example, if they say that their favorite food is pizza, you can suggest getting pizza together sometime. Or, if they say that their favorite movie is The Shawshank Redemption, you can talk about how much you love that movie too and maybe even quote a few lines from the movie.

18. Do You Have Any Hidden Talents?

Hidden talents can sometimes border on the weird and wonderful. But, it's always fun to find out what hidden talents the other person has.

Do they have any weird or wacky skills? Can they do any magic tricks? Are they double-jointed? Do they have a photographic memory?

This question can lead to some really fun conversations. And, you might even be surprised by the hidden talents that the other person has!

19. Do You Like to Dance?

Dancing is a great way to let loose and have some fun. It's also a great way to get some exercise. So, if the other person says that they like to dance, you can suggest going dancing together sometime.

Or, if they don't like to dance, you can bond over the fact that you both don't like to dance. Either way, it's a great way to get to know the other person better.

20. Who Is the Most Influential Person in Your Life?

People usually answer questions about themselves, but this question encourages them to talk about another person.  This question can lead to some interesting conversations about the most influential people in their life.

You might find out that they are influenced by their parents, a friend, or a celebrity. Or, you might find out that they don't have anyone who is particularly influential in their life.

What Not to Do

There are some things that you should avoid doing when starting a conversation online. Here are some examples:

  • Don’t ask personal questions right away. You want to build up to it so that the other person doesn’t feel like you’re interrogating them.
  • Don’t ask yes or no questions. These can be difficult to answer and they usually don’t lead to interesting conversations.
  • Try to avoid talking about controversial topics like religion or politics. You want to keep the conversation light and easygoing at first.
  • Don’t send a generic message. This just shows that you didn’t bother to read their profile and it makes you look lazy.
  • Avoid using cliche phrases like “What’s up?” or “How are you?” These are boring and they don’t really give the conversation a good start.
  • Avoid cheesy pick-up lines. These are usually corny and they tend to fall flat. Plus, the other person might think you’re just trying to get them into bed!

You might also be interested in our article titled: Single Women's Biggest Complaints About Online Dating Sites


So, whether you’re just starting out on your online dating journey or you’ve been at it for a while and are looking for new conversation starters, we hope this list has given you some ideas.

These are some great conversation starters for online dating. Use them to your advantage and you’ll be sure to have some meaningful conversations with the people you meet online.

Will you try any of them the next time you get on a dating site? Let us know how it goes!

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