How to Keep the Conversation Going on an Online Date

“It takes two to tango.” That’s the age-old adage that applies when it comes to conversation. Whether you’re on a real-life date or an online one, keeping the conversation going is an important part of getting to know someone better. So how do you ensure your online conversations flow smoothly? Here are some tips for making sure your virtual dates keep the dialogue going and create an intimate connection between both parties.

Online dating can be tricky at first, especially if you don’t feel comfortable in a digital space. However, with just a few simple steps, you can start building trust and creating positive energy during your chats. The key is to ask meaningful questions that make your date feel seen, heard and understood – because these are the essential ingredients needed for any kind of successful relationship.

By focusing on topics that bring out each person’s interests and values, as well as asking follow-up questions about their answers, you’ll be able to keep things interesting while simultaneously deepening your emotional bond with each other from afar. With this guide, you’ll have all the tools necessary for maintaining vibrant dialogue with your online partner – so get ready for sparks to fly!

1. Ask Open-Ended Questions

Asking open-ended questions is one of the best ways to keep a conversation going on an online date. It gives you, and your potential partner, a chance to really delve into something meaningful – or even just lighthearted. Rather than simply asking yes/no questions that can end up feeling like a job interview, why not ask something more engaging? For example, what are some of their favourite hobbies or activities? What type of music do they listen to? Or even share stories about past experiences. This helps build rapport by giving insight into someone’s interests and values.

It also helps if you find common ground with each other; this could be anything from shared places travelled to similar beliefs or political views. Asking about these topics can help create intimacy between two people as it allows for conversations that come straight from the heart. Plus, when there’s mutual agreement on certain issues, it can bring two strangers even closer together! When in doubt, don’t be afraid to try out different topics until you both find something that ignites further dialogue – knowing where to draw inspiration can go a long way in keeping things interesting during an online date.

2. Find Common Ground

Talking and connecting with someone on the internet can be like walking along a tightrope; you need to keep finding ways to make sure both of your feet remain firmly planted. Finding common ground between two people is essential for keeping an online conversation going, so it’s important to take advantage of this opportunity! Here are three tips that’ll help ensure your conversation keeps rolling:

1) Start by asking questions about their hobbies or interests- what books do they read? What kind of music do they listen to? Do they have any favourite recipes or restaurants? These kinds of open-ended questions give them ample room to talk and provide more insight into who they really are.

2) Look through both of your profiles for topics that you share in common. This could include anything from educational backgrounds, sports teams, shared cultures, mutual friends – even pets if you both happen to have one! It’s amazing how many things we can learn about someone just by looking at a few pictures and posts.

3) Share stories and experiences that relate back to these commonalities. Whether it’s talking about funny moments growing up or embarrassing blunders throughout adulthood, discussing similar life events will only bring the two of you closer together. Laughing together over shared memories creates a special kind of bond which is often difficult to find in traditional relationships.

By taking some time out each day to discover new things about each other, not only does the conversation stay interesting but it also deepens the connection between two people exponentially. Instead of feeling nervous about conversing with someone online, embrace this chance as an exciting adventure where no topic is off-limits!

3. Stay Positive

Keeping the conversation going on an online date can be daunting, but staying positive is key. Like a ray of sunshine piercing through the clouds of awkwardness and uncertainty, it helps to stay upbeat in order to keep things flowing smoothly.

A great way to achieve this is by focusing on topics you both find interesting. Making sure you are aware of each other’s hobbies or interests beforehand can really help build common ground that will lead to more meaningful conversations throughout your date. Similarly, try to steer away from any negative topics such as politics or religion if possible – these could quickly take a turn for the worse! Instead, focus on lighter topics like favourite TV shows or music artists; these conversations tend to open up naturally without much effort required. Furthermore, always make sure you are listening carefully to what your date has to say too so they feel heard and appreciated – don’t forget there should be two-way communication!

4. Listen Carefully

Eagerness versus stillness – that’s the challenge when it comes to keeping a conversation going on an online date. You want to show your enthusiasm, but you don’t want to come off as too eager. Listening is key:

1) Being present and attentive in each moment;

2) Not just hearing what they have to say, but really listening for deeper meaning;

3) Taking time to think before responding with thoughtful questions or comments.

When it comes down to it, connecting isn’t about speaking – it’s about being heard. When you listen carefully and put yourself in their shoes, it can deepen the connection between you two far more than any witty remark ever could. It takes practice (and some courage!) but if done right, this kind of deep listening will help build a strong foundation of trust and understanding that can sustain your relationship over long distances and even beyond the screen. As we move into maintaining eye contact, remember that true intimacy lies not only within words spoken but also within those left unsaid.

5. Maintain Eye Contact

Have you ever felt like your conversation is dying on an online date? Maintaining eye contact is essential to keeping the conversation going. It may be difficult to do this with a computer screen between you and the other person, but there are still ways that we can make meaningful connections without being in the same room together.

For starters, try looking directly into the camera instead of at the face on the screen. This will help create a sense of presence when talking to each other. Additionally, it’s important to give your undivided attention while they speak. That means no multitasking or checking notifications during conversations! Showing genuine interest in what they have to say will keep them engaged in the conversation and make sure that things don’t fizzle out prematurely.

Taking time for pauses throughout your exchange also allows for a natural flow and more intimate moments as well. Pauses don’t necessarily mean awkward silence; rather, it provides space for thoughtful reflection which encourages deeper connection. As long as both parties remain attentive and generous with one another, maintaining eye contact can help bring back life into any stagnant chat session – so let’s keep those connections alive!

6. Use Humor

Humor can be a great way to keep the conversation lively while on an online date. It helps break any tension that may have built up, and it allows both partners to relax in the conversation. Plus, laughter is often a sign of connection between two people – which is what we’re aiming for! Make sure your jokes are respectful and appropriate though; you don’t want to accidentally offend your date. Once you’ve become comfortable enough with each other to make light-hearted jokes about one another or life in general, you’ll find that the conversation will flow much more easily.

When using humor during an online date, remember that timing is everything. You don’t want to tell too many jokes at once as this could come across as overbearing or desperate. Instead, sprinkle them throughout the chat session so they feel more natural and organic. Additionally, listen closely to your date’s responses – if there isn’t a lot of engagement after making a joke then maybe try changing topics instead of pressing forward with humor.

TIP: If all else fails, watch some standup comedy together! Watching something funny can help ease the awkwardness of a first or second virtual meetup and give you both something to talk about afterwards.

7. Connect Through Shared Interests

Connecting through shared interests is a great way to keep the conversation going on an online date. It provides an opportunity for you both to get to know each other more deeply, and before you know it, hours have gone by! To make this happen, try asking open-ended questions that encourage your date to talk about themselves. This will give you insight into what they like or don’t like and can reveal commonalities between the two of you.

You could also share some stories about yourself – people love talking about their own experiences! You’ll find that everyone has something interesting to say if given a chance, so just go with the flow and see where the conversation takes you. Who knows? Perhaps one day, you might even decide to explore those passions in real life together!

8. Discuss Your Hobbies

As the warm, digital rays of your computer screen embrace you, there’s a thrill in the air. You and your online date have been talking for hours now, exploring each other’s stories and personalities with every passing word. Now it’s time to take things one step further: discussing hobbies!

Hobbies are often more than just activities; they can be windows into someone’s personality. Take a closer look at who they are – what do their leisurely pursuits reveal? Here’s how to discuss your hobbies on an online date:

• Talk about why you love them – What made you pick up that particular hobby? How does it make you feel when you’re doing it?

• Share funny anecdotes or experiences – Was there ever a moment when something went hilariously wrong while pursuing this activity?

• Ask questions about their hobby – Is there anything unique or interesting about how they approach it? Are there any fun facts related to this pastime?

• Suggest trying out new things together – Have either of you ever wanted to try something but haven’t yet had the chance? Perhaps consider taking some classes remotely as part of your budding relationship!

• Laugh and enjoy yourselves – Don’t forget to lighten the mood and have fun with each other during the conversation. Remember, laughter is key!

By learning more about each other through these conversations, both of you will get much closer in no time. Who knows where else your shared interests may lead?! Let’s move on to talk about current events–a great way for two people from different walks of life to connect over common topics.

9. Talk About Current Events

Catching up on current events can captivate conversation, creating connection and camaraderie between two people. Checking in on the news of the day brings a breath of freshness to your online date. It’s an opportunity for animated exchange as you both share opinions and perspectives about what’s happening around the world.

Discussing relevant topics can be interesting and enlightening. Ask your date if they’ve read any articles recently that have caught their attention or heard anything from friends or family about what’s going on in their hometown or abroad. You may be surprised at some of the stories your date has to tell!

Take this moment to get creative with conversation topics – explore new avenues for getting to know each other better!

10. Get Creative With Conversation Topics

Have you ever wanted to get creative with conversation topics on an online date? Here are a few ideas that can help keep the conversation going:

  1. Ask about their favorite movies, books, or music and why they like them.
  2. Share funny memories from childhood or stories of your upbringing.
  3. Discuss current events in pop culture or news headlines.
  4. Talk about random facts that you have learned recently!

These topics add some fun and excitement to conversations by allowing for more creativity than just discussing work or hobbies. Sharing experiences and learning things about each other helps build intimate connections between two people on a date, so don’t be afraid to take risks with interesting topics! You may find out something surprising about your date or learn more about yourself as well – either way it is sure to make the conversation even more engaging!

Frequently Asked Questions

What Is Your Favorite Type Of Cuisine?

Talking about food can be a great way to get closer on an online date – it’s something everyone has in common! So why not ask your date what their favorite type of cuisine is? Not only will you learn more about them and the things they like, but it can also lead to other conversations that are just as interesting.

Maybe they love Italian food because they’ve been to Italy before or maybe they’re really into Japanese flavors because of all the anime shows they watch. No matter what answers you get, talking about food can help keep the conversation going in a fun and lighthearted way. Plus, if all else fails, at least you both have something tasty to look forward to enjoying together once this pandemic ends!

What Do You Like To Do For Fun?

When it comes to having fun, everyone is different. It’s great getting to know someone and finding out what makes them tick. There are usually a few activities that we all enjoy, so let’s talk about those! Here are some of my favorite things to do for fun:

• Going on hikes and exploring nature – I love the fresh air and feeling of accomplishment after conquering a trail. • Watching movies or shows with friends – Curling up in a comfortable spot with snacks and spending time laughing together is one of life’s pleasures. • Trying new recipes – Cooking can be really creative, especially when using unique flavors from around the world. Plus there’s something special about eating dishes you made yourself! • Playing board games – Games like Monopoly or Trivial Pursuit bring out our competitive sides while also allowing us to bond over shared experiences.

No matter how much different we may seem at first glance, chances are good that if two people have their own ideas of fun then they’ll find plenty of common ground too. Getting to know each other better through conversation helps create an understanding between both parties and builds anticipation for future dates!

What Are Your Thoughts On Politics?

Politics is a hot-button topic, especially in 2020. Did you know that over 68% of people have strong opinions on political issues? With that said, it’s important to ask your date their opinion on politics during an online date. Asking this question can break the ice and lead to further conversation topics if both parties have different views.

Getting into conversations about politics can be daunting but it doesn’t have to be uncomfortable or hostile. Ask open-ended questions like “How do you feel about the current state of affairs?” or “What are some of your thoughts on recent events?” This will allow your date to share more information and keep the conversation going without feeling overwhelmed with negativity. It also gives them a chance to talk about what they’re passionate about which can show off how smart, articulate and interesting they are!

When having these discussions, make sure to respect each other’s point of view even if someone disagrees with yours. Listening actively and responding thoughtfully is key for keeping the conversation going in a positive direction. Remember, there isn’t always one right answer when discussing politics so focus on learning from each other rather than trying to win arguments.

If You Could Travel Anywhere In The World, Where Would It Be?

Travelling is a passion that many people share. According to one survey, more than 80 percent of Americans have travelled outside the country at least once in their lives! If I could travel anywhere in the world, it would be South America. From lush jungles and vast deserts to ancient ruins and buzzing metropolises – it’s no wonder why so many people flock there for an unforgettable experience.

I’d love to see Machu Picchu in Peru, spend some time exploring Rio de Janeiro, Brazil, or wander through Colombia’s vibrant streets filled with art galleries and markets. There’s something about immersing yourself in a culture so different from your own that can be truly magical – even if only for a few weeks. Plus, you never know what kind of stories you’ll come back home with!

No matter where we choose to go on our vacation, having someone special by our side makes it all the more exciting. Travelling together is a great way to get to know each other better while experiencing new things and making memories along the way.

What Do You Value Most In Life?

When it comes to what we value in life, there’s so much that shapes our outlook and perspective. Whether it be family, friends, experiences or other things, every person is different – and that’s a beautiful thing! We all have unique values that make us who we are, and conversations about them can really bring us closer together.

Getting into what someone values most gives you an insight into the things they find important in their lives. You can learn how they view relationships, ambition and goals; get to know how they see the world around them. Asking this question is also a great way to open up your own thoughts on these topics too – letting each other explore ideas with one another.


It’s important to keep the conversation going on an online date. Finding common ground and topics of interest is a great way to make sure you both have something to talk about! Asking open-ended questions like, “What do you like to do for fun?” or “If you could travel anywhere in the world, where would it be?” can help spark interesting conversations. Showing genuine interest in your partner’s interests will also help create a positive dynamic between the two of you.

Ultimately, how successful an online date goes comes down to communication and connection. Ask meaningful questions that allow your partner to share more deeply what they think, feel and value in life. That kind of openness builds trust quickly – almost as fast as lightning flashes across the sky – so use this time wisely and enjoy getting to know each other better!

Be yourself and don’t forget to have fun with it! You never know what amazing connections you might form by simply having an honest conversation with someone new. So take some time out of your day to chat with someone special; you won’t regret it!

Bernadine K. Darrell, MSW
Bernadine K. Darrell, MSW
Bernadine is a Marriage & Family Therapist with an MSW from University of South Florida. They specialize in couples & family therapy using evidence-based techniques with a focus on respect, compassion & empathy. In their personal life, Bernadine has a passion for art & incorporates it into therapy through creative interventions.

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