How to Start an Online Conversation

You might be trying to get to know someone new. Email, dating websites, and messaging services make it easier to stay connected with friends and family, but it can still be hard to start a conversation with someone you haven't met in person. More and more people are meeting friends, partners, and spouses online, and this can make anyone feel a bit awkward! Be curious, but not pushy; relax, and just be yourself.

Stop overthinking. If you're trying to get to know someone (and maybe even flirt a little), the goal of the first few online chats is to let them know who you are. You want to be yourself, and following a script will only take you further from your goal.

• Starting an online conversation is tough for most people. You’re neither the first nor the last to feel this way.
• At worst, this will be an experience. At best, it could turn into a meaningful relationship. Nothing happens until you try.

Pick the right time. Message them when they're online. It's much easier to start a conversation in the moment rather than waiting for a response later.

• Choose a time when you're not on the move. You don't want to feel stressed, and you want the conversation to flow smoothly for the best chance of progressing.

Start with small talk. Send them a short message and ask how they've been. For example, "Hey, how have you been?". Once you kick off the conversation, it gets easier – there’s no turning back!

• They’ll likely reply to “how’s it going,” then ask about you. Be ready with your response.
• Avoid short answers like "I’m fine". Anyone can say “fine.” Let them know more about you, like "I’m doing great! Today, my friends and I explored an abandoned house on a hill. It was amazing but kind of creepy" or "My dance team made it to the national team. I’m really excited!"
• Share things that excite you but avoid boasting.

Ask about common interests. This is a classic and sincere way to start a conversation. If you’re in the same class, ask about the homework. If you’re in the same club, ask about upcoming events. It’s a great way to start naturally, removing the initial barriers for a deeper chat.

• Try saying: "Oh, I forgot to do the English homework today. Have you done it yet?"
• Or: "Hey, do you know when the next competition is? I didn’t catch when the coach mentioned it during today’s practice…"

Give them a compliment. If someone does something praiseworthy, of course, you should compliment them. This is another great way to start a conversation and make them feel appreciated. Don’t overdo it though – too many compliments can come across as flattery.

• If you’re in the same class: "You did an amazing job on that presentation today! I never realized how much I’d learn about Ulysses S. Grant!"
• If you’re on the same team: "You did an excellent job in today’s 91 km sprint. You really supported the team well."

Ask a question. If you met someone on a dating site like OKCupid or a dating app like Tinder, you may not have any real-life connections to chat about. Ask them an open-ended question about themselves. Their profile will inspire you.

• For example: "I see you’re into hip hop. Are there any good shows lately?"
• Or: "I really like your beard. How long have you been growing it?"

Be cautious with pick-up lines. Pick-up lines can have the opposite effect you expect: they might work for some people, but push others away. Lines that come off as cheesy or manipulative, especially if they don’t align with how you view yourself, can turn people off. Impress others with authenticity, and if that includes a pick-up line, be true to yourself!

Be ready to engage in the conversation. Read messages carefully and respond thoughtfully. A good conversation involves picking up on cues and understanding what the other person is saying. While chatting with them, pay attention to both the content and the flow of the conversation.

• In this regard, online chats can be even easier than face-to-face conversations. You can revisit the chat if you need to recall a specific detail.

Ask questions. Show real interest in the other person. Science has shown that people love talking about themselves. If you ask someone something, they’ll likely have plenty to say.

• Ask questions that lead to more questions. For example, if you ask "What kind of music do you like?" and they respond "I like all sorts of music—rock, pop, punk. I watch a lot of local music shows."—follow up with, "Are there any good music shows on lately?"
• Avoid yes/no questions. A simple "yes" or "no" answer can shut down a conversation. If you need to ask a question with a simple answer or two possibilities, be prepared with a follow-up question.

Don’t be too nosy. Be cautious when broaching sensitive topics. You’ll need to use your intuition here, but as a general rule: Don’t ask anyone a question you wouldn’t want to answer yourself.

Turn your answers into questions. A conversation is a two-way street, and if you want it to continue, you need to keep the momentum going once you’ve spoken. After sending a message, end with a question so the other person can respond.

• Think of it like a game of catch. If you catch the ball, great—but the game doesn’t continue until you throw it back to someone else.
• Don’t just say, "I had a great day. I think I did well on the math test!" Instead, say, "I had a great day. I think I did well on the math test! How about you?"

Don't be afraid to talk about yourself. There’s a delicate balance here: if you dominate the conversation with only talk about yourself, the other person might feel you’re selfish or vain; but if you never share anything personal, you’ll just seem mysterious.

• Be genuine. If you lie—embellishing your life or pretending to be someone else—it will backfire. Eventually, the truth will come out.
• If they ask about you, answer, but try to turn your response into a question. For instance, if asked about your dog, you might say: "His name is Duke. He’s a Border Collie. We rescued him from a cave three years ago, and now he’s like a family member. Do you have any pets?"

Use emoticons and picture characters, but don’t overdo it. Emoticons like ":)" and ":3" can add emotion and spice to your words, helping to express feelings in the objective world of online communication. They can make others like you more and help you come across as friendly. However, emoticons can reveal a lot about how you’re feeling: if someone uses a lot of smiley faces, they might be into you.

• There’s nothing wrong with expressing your emotions, but depending on the situation, you might want to be playful or wait until you understand the other person better. Be cautious with emoticons and what they imply.
• If you want to subtly let someone know you like them, use ":)". In practice, use that emoticon when you’re genuinely smiling in real life :)

Don’t force it. If the person only responds with one-word answers, despite your best efforts, they might not want to talk at that moment. If the conversation feels forced, it’s okay to wrap it up and try again later.

• It’s not necessarily your fault! It’s hard to gauge someone’s mood, especially online. Maybe they don’t want to talk because they’re feeling down, have a lot on their plate, or just had an argument with their parents.
• If you keep trying to talk to someone and they seem uninterested, stop pushing. Try to spend more face-to-face time with them if you can, but only if you have a genuine reason for doing so.
• Give them some space. No one likes feeling pressured. It’s often better to let someone go than to make them uncomfortable.

Keep chatting until there's nothing left to say. Maybe you've really run out of topics or need to leave. Either way, you'll need to say goodbye.

• Say something like, "I have to go to class now. It was great chatting with you. Have an amazing day!"
• Consider saying you have to leave, even if you don't really have to. It’s an easy way to wrap up the conversation without seeming rude.

Don't feel like you need a formal plan. Online conversations follow a slightly different protocol than in-person chats. It’s not too formal. Unless the other person has limited internet access, you don't need to set up a "second date." You can simply say, "Let’s talk again sometime!"

• If the conversation goes well, just message them again after a day or two when both of you are online. This time, try getting to know each other better. Continue chatting based on the information and jokes you've already shared.
• If the other person can only access the internet at specific times (for instance, three hours every afternoon or just at the library), you can plan a formal time. For example: "I really enjoy talking with you. I know you’re not always online—could I schedule a chat with you on Tuesday?"

Be cautious. If you plan to meet in person, use your best judgment for the situation. A conversation can tell you a lot, and people aren't always the same as they seem online.

• Consider talking to the person more online before moving to a face-to-face meeting.
• If you're using an online dating site like OKCupid or Tinder, you might decide to meet up with someone sooner—or even right away. Use your best judgment. If you’re meeting a stranger, let a friend know where you’re going and who you’re meeting. Bring your phone, and if possible, meet in a public place (like a coffee shop) during the day.