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Connect meaningfully: 13 ways to start a real conversation online

May 12, 2022 - 15 min read


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13 ways to start a conversation online

The key to meaningful online relationships

How to start a conversation online with a stranger

6 pros and cons of online conversations

How to maintain an online friendship

Trust yourself

We spend more time online than ever, especially since the COVID-19 pandemic began. We work from home, chat with friends through video calls, and spend the time in between browsing social media. In fact, about 30% of Americans say that they are now almost constantly online

All this means you might be wondering how to start a conversation online.

The world has changed, and we have to re-think how to navigate online relationships. When we use chat apps, we can’t depend on non-verbal cues like tone or body language. If you’re starting a conversation online, there’s also an added layer of uncertainty when firing off that first message. The risk of rejection feels higher than ever.

Whether it’s a stranger, a new colleague, or an online friend, we’re happy to report that it’s possible to have healthy text conversations. Follow this guide to learn how to start a conversation online and start making new connections.


13 ways to start a conversation online

There are many fun ways to connect with others online. Here are some tips on how you can start a conversation with anyone, whether that’s an online friend or a professional connection:


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The key to meaningful online relationships

Building a meaningful relationship online is similar to forming one in person. Here are three tips for making more authentic connections:

  1. Admit when you don’t know something. You’re not there to impress them. You’re there to connect. The best way to do that is by acknowledging your humanity. When you admit you don’t know something, you’re admitting to the most human trait of all: fallibility. 
  2. Be vulnerable. This means sharing what you really think and feel. You don’t have to let everything out at once, but sharing just a little can help you build more authentic connections. 
  3. Know what you want and ask for it.  If you’re looking for guidance from a mentor, tell them. If you would like to go on a date, be clear about it. This kind of communication sets clear expectations for what you want out of the relationship.

How to start a conversation online with a stranger

Our basic tips for how to start a conversation online work in most scenarios. However, we have some bonus tips for the different types of relationships you might form online. Knowing how to talk to a stranger is difficult, but tailoring your approach for each situation will help you start strong.


How to form an online friendship

Here are some ways to approach making friends online:

1. Join an app centered around making friends

Online forums like Reddit can help you find people with shared interests. You can also use apps like Snapchat, Tinder, Bumble BFF, MeetUp, or Nearify to connect with people in your area.

2. Network on social media

If you follow someone on Twitter that shares common interests, try reaching out to see if they’d like to grab coffee over Zoom or Facetime. These virtual face-to-face interactions are much easier than constant messages back and forth. You probably have things in common if you chose to follow them on social media, so you have a great foundation to work with.

3. Be yourself 

Be authentic when you reach out. Trust that you’re good enough. People will respond if they sense you’re confident. Be honest about who you are instead of putting up a charade.

4. Try an online class

Online fitness classes or skill-building classes can provide you with opportunities to meet people with similar interests. If you’re taking a coding class for work, forming a study group with some of your peers will help you socialize while working together on assignments. 

Or, other students in a French class can help you practice over text or group calls. It’s hard to start a conversation online with a friend who doesn’t speak the same language, but at least you’ll both be learning.

Dipping your toes in online dating

The rules of good online conversations apply to dating, too. You wouldn’t start a conversation with a business connection by giving them too many compliments, right? You should avoid it with new online dating connections, too.  Here are some tips to starting online conversations with potential romantic matches: 

1. Develop your online profile

Regardless of what platform you’re using, you need to make sure that your profile reflects who you are. Use photos where you’re smiling and relaxed or that you feel represent your personality. Mention some of your favorite things — movies, bands, places — so people have something to start a conversation with. 

2. Match with people who share your interests

Once you find someone to talk to, look at their profile for potential ice breakers. They might mention a favorite movie or TV show or have a photo in a foreign city that you’ve visited. Look for common ground and ask open-ended questions to start a conversation. 

Don’t list interests that you think other people will want to read. If you hate waking up on Saturday morning to go hiking or using your weekends to go camping, avoid adding “hiking” or “outdoorsy” to your profile. That way, you’ll be able to actually find people with who you have shared interests. These things will act as good conversation starters. 

(This tip isn’t useful just for dating — it’s a fundamental part of starting any meaningful relationship).

3. Get personal (if things are going well)

Simple questions and small talk become stale if you’ve been chatting a while. After you make your first impression, look for conversation topics that will strengthen your bond. If you can keep a conversation going about movies for an hour over Zoom, it might indicate that you can move beyond a first date conversation and into something personal.


What about remote work relationships?

Networking online is remarkably easy thanks to platforms like LinkedIn and email. And with a majority of remote employees feeling left out at work, learning how to start a conversation online is more important than ever. 

Grow your professional network and connect with your coworkers online using these tips:

1. Endorse what they say

If you agree with or admire a person, share their posts on LinkedIn or Twitter. You can even add a thoughtful comment about what they said. It’s a small gesture, but people enjoy feeling heard. That small interaction will create a foundation for you to reach out to them later to ask about work experience or mentorship opportunities.

2. Be humble

Soften your language when you reach out to this person online. Avoid sending a message that’s too direct, or you might come off as arrogant. Acknowledge that you’re reaching out of the blue, explain why you want to speak with them, and thank them for their time. This tactic is especially helpful when dealing with busy people. 

3. Compliment them 

If you’re reaching out to someone for the first time, compliment them on something specific. Mention that they gave a great online presentation at a conference or you appreciated their post in a forum. This will open the door to discuss whatever they did further and indicate things that you’re both interested in.

4. Start small

Maybe you’re looking to deepen a relationship you have with a coworker that you’ve never met before. Reach out and start a conversation with them about something small. For example, you could share your excitement about a new initiative starting at your company. It will be a great way for you to chat and become friendly without jumping in headfirst.

6 pros and cons of online conversations


In the early days of the internet, naysayers said it could never replace genuine social interaction. They weren’t entirely wrong, but they also weren’t entirely right. Like most things in life, online communication has clear pros and cons.

The pros

You can meet people from anywhere. Thanks to the internet, you can make friends and connections from anywhere. You can find friends to visit in another country or new professional connections in another state. 

It’s easier to express yourself. On some social media platforms, anonymity makes it easier to express yourself. No one knows who you are, so the chances of embarrassment are less severe. This allows even the shyest people to connect with others.

It’s convenient. Making friends in person takes time. It requires us to travel and meet at a physical location. Plus, it may take multiple meet-ups to make meaningful connections. Chatting online takes away some of these burdens.

The cons

Most online friends stay online. Unless you make meeting a priority, online friends rarely translate to real-life meet-ups. 

Internet addiction is possible. Internet friends can make us feel like our social needs are met. But in reality, we’re still not seeing people in person — which is vital for our well-being. We need to strike a balance between online and real-life human connections.

You lose out on non-verbal cues. Eye contact, body language, and tone of voice add a lot to a conversation. We can try to make up for it with exclamation points and emojis — but texting still misses these core parts of communication. 

How to maintain an online friendship

Keeping up with the people in your life is difficult — especially if you don’t live in the same city. But don’t worry: there are plenty of ways to stay connected to someone virtually. Here are 6 easy ways to maintain an online friendship:


  1. Schedule time to speak, whether that’s a monthly phone call or a weekly check-in
  2. Follow-up on things you know are happening in their life, like a new job or promotion
  3. Reach out to share updates, even when they don’t ask for it
  4. Send them small things that you think they’d like
  5. Take an online course together 
  6. Don’t lie or say things you don’t mean

Trust yourself

These days, it’s more common than ever to meet people online. Whether through a dating app, social media, or online gaming, the Internet is a great tool to forge meaningful new connections. As long as we continue to meet our real-life social needs, online friends can be an excellent outlet for authentic interactions. 

BetterUp can help you develop the social skills you need to grow personally and professionally. Knowing how to start a conversation online will bolster your professional network, develop your active listening skills, and help you find your next best friend

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Published May 12, 2022

Elizabeth Perry

Content Marketing Manager, ACC

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