13 ways to start a conversation online

We spend more time online than ever, especially since the COVID-19 pandemic. 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 they’re almost constantly online.

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

The world has changed, and we have to rethink 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, new colleague, or online friend, we’re happy to report that it’s possible to carry an enjoyable conversation. Follow this guide to learn how to start a conversation online and make new connections.

13 ways to start a conversation online

There are many fun ways to connect with others online. Here are some strategies and tips for starting a conversation with anyone and making professional connections:

1. Join an online forum like Reddit to find people with shared interests

2. Be active in relevant online communities, like your work Slack or a group chat

3. Find people in your area on social media like LinkedIn or Twitter

4. Trust yourself and be authentic

5. Develop online profiles that reflect your personality

6. Ask lots of questions, including follow-up questions, to find common ground and express interest

7. Use conversation starters to prompt new topics

8. Remember that people are busy and might be slow to answer — be patient

9. Compliment things you like about the person, like their presentation skills

10. Read their messages thoroughly, just as you would listen actively 

11. Share things you think the person would enjoy, such as articles or news tidbits

12. Act the way you would in person

13. Be brave and keep going even if it’s hard at first — it gets easier

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 might mean sharing your opinions or reaching out first. You don’t have to be unprofessional about it, but just be yourself so others feel they can too. 

3. Know what you want and ask for it. If you’re looking for guidance from a mentor, tell them. If you’d like to do a presentation with a coworker, be clear about it. This kind of communication sets transparent expectations for what you want out of the relationship.

How to start a conversation online with a stranger

Our basic tips for starting conversations 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 strangers is difficult, but tailoring your approach for each situation will help you start strong.

Forming 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 from.

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.

During your first hangout, consider suggesting a conversation opener like “20 questions” to share a bit about yourself and better understand the other person. 

4. Try an online class

Online fitness or skill-building classes offer 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? Avoid it with new online dating connections as well. Here are some tips for starting online conversations with potential romantic matches: 

1. Develop your online profile

Regardless of the platform you use, make sure your profile reflects who you are. Use photos where you’re smiling and relaxed and that 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

While dating sites call themselves “matchmakers,” getting a date requires more work than simply matching with someone. 

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

Don’t list interests you think others want to read. If you hate waking up on Saturday morning to go hiking or camping, avoid adding “hiking” or “outdoorsy” to your profile. That way, you’ll be able to actually find people with 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 making your first impression, look for conversation topics to strengthen the bond.

If you can keep a conversation going about movies for an hour over Zoom, it might indicate you can move beyond a first-date conversation and into something personal and even a little flirty.

Starting conversations with remote work coworkers

Networking online is fairly easy thanks to platforms like LinkedIn. 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 befriend coworkers online using these tips:

1. Endorse what they say

If you agree with 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 later to ask about work experience or mentorship opportunities.

2. Be humble

Soften your language when reaching out online. Avoid sending a message that’s too direct, or you might come off as arrogant, not confident. 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. Express your admiration

Chances are, you’re reaching out to someone you admire who caught your attention somehow, so a great way to start the conversation is with a compliment. Mention that they gave a great online presentation at a conference or you appreciated their post in a forum.

This opens the door to further discuss what they did and indicate things you’re both interested in.

4. Start small

Maybe you’re looking to deepen a relationship with a coworker 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 to chat and become friendly without jumping in headfirst.

Conversation starter examples

Here are a few interesting conversation starters for different scenarios: 

• “Tell me about you.” While broad, this prompt allows the other person to highlight information they actually want to share instead of answering precise questions from the get-go. Ask follow-up questions to get more detailed answers and show you’re actively listening. 

• “If your day suddenly freed up, what would you do?” This is a great new-friend conversation starter. It’s more interesting than “How are you?” and prompts the listener to think about enjoyable hobbies and adventures. 

• “How do you spend most of your free time?” This question prompts introspection and curiosity. You’ll learn a lot about the other person, and they’ll feel cared for and heard. Maybe it’ll even remind them to enjoy more free time out of their day. 

• “When’s your next big adventure?” Start on an excited note by asking the listener to think about their next vacation, camping weekend, or late-night show. Their answer will also hint and shared — or not so shared — interests. 

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 — 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. You’re typically bonding over virtual activities, like video games, or you might both feel nervous about meeting in-person. 

Internet addiction is possible. Internet friends can make you feel like your social needs are met. But in reality, you’re still not seeing people in person — which is vital for your well-being.

To strike a balance between online and real-life human connections, try a periodic digital detox and prioritize in-person meet-ups. 

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. But there are plenty of ways to stay connected to someone virtually. Here are six ways to maintain an online friendship:

1. Schedule a time to speak

2. Follow-up on things like a new job or promotion

3. Reach out to share updates

4. Send small things 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, learning how to start a conversation online can lead to forging meaningful connections.

As long as we continue to meet our real-life social needs, online friends can be an excellent outlet for authentic interactions.