Striking up a conversation online is hard for almost everyone. You’re not the first, and you won’t be the last. Worst case, it’ll be a learning experience. Best case, you’ll connect with somebody in a deep way. Neither case applies until you try.
Pick a time when you don’t have anywhere to be. You don’t want to be stressed-out, and you want to give the conversation a chance to grow.
They will likely respond with how they’re doing, then ask you how you’re doing. Be prepared to say how you’re doing. Avoid dead-end answers like “I’m good. " Anyone can be “good”. Respond with something that tells your conversation partner about who you are, such as “I’m good! My friend and I explored this abandoned house up in the hills today. It was really cool but super spooky” or “My dance team just made it to nationals. I’m so excited!” Mention things that make you seem interesting, but avoid bragging.
Try something like this: “Hey- I completely blanked and forgot to write down the homework for English today. Did you happen to get it?” Or this: “Hey, do you know when our next track meet is? I must have tuned out when coach announced it during practice today. . . "
If you’re in a class together: “You did a great job on your presentation today! I never thought I’d learn so much about Ulysses S. Grant!” If you’re on a team together: “Nice work in the 100-yard sprint at the meet today. You really put the team on your back”
For example: “I see you’re into hip hop. Been to any good shows lately?” Or: “I dig your beard. How long have you been growing that sucker?”
In this respect, talking to people online can even be easier than speaking in person. You should be able to scroll back through the conversation if you need to remember a specific detail.
Ask questions that lead into other questions. If you ask “So what kind of music are you into?” and they respond “I like a lot of music- some rock, some pop, some punk. I go to a lot of local shows”–ask them something like, “Been to any good shows lately?” Avoid asking yes-or-no questions. A simple “yes” or “no” can stop a conversation in its tracks. If you must ask questions with basic or binary answers, be prepared to ask follow-up questions.
Think of a conversation like a game of catch. If you catch the ball, then that’s great–but the game cannot go on until you throw the ball back to the other person. Do not merely say, “My day was good. I think I did really well on my math exam!” Say, “My day was good. I think I did really well on my math exam! How was yours?”
Be honest. If you weave a web of lies–building yourself up to be something you’re not–it may come back to bite you later on. [5] X Expert Source Maria AvgitidisMatchmaker & Dating Expert Expert Interview. 20 December 2019. Things have a way of coming to light. If your conversation partner asks you about yourself, answer- but try to turn your answer back into a question. If they ask you about your dog, for example, consider something along the lines of: “His name’s Duke. He’s a border collie mix. We saved him from a shelter three years back, and he’s like one of the family now. Do you have any pets?”
It is not wrong to reveal your feelings, but depending on the situation you may want to play it cool until you’ve gotten to know someone better. Be careful with your emoticons and what they tell your conversation partner. If you want to subtly let the person know that you’re interested, then make use of the “:)”. As a rule of thumb: use it at points in the conversation when you would actually smile in real life :)
It is not necessarily your fault! It can be so difficult to tell how someone is feeling, especially online. For all you know, the person doesn’t want to talk because they’re feeling depressed, or they have a lot of work to do, or they’ve just had a fight with their parents. If you try to talk to someone over and over again and they do not seem interested in conversation–let it go. Try to get to spend more time with them in person, if possible, but only if you have a good reason to do so. Give them space. Nobody likes to feel pressured. It is better to let someone go than to make them feel uncomfortable.
Say something along the lines of, “Alright, I need to go to practice. Nice talking to you! Have a great day”. Consider saying that you have to go, even if you don’t actually have to go. This is an easy way to get out of a conversation without feeling rude.
If the conversation went well, simply message the person again in a day or two when you are both online. This time, you should be more familiar with each other. Build upon the information and the jokes that the two of you shared in your first conversation. If your conversation partner can only access the internet at certain times or in certain places (say, for three hours each afternoon, or only at the public library), then feel free to make a formal plan. Type something like, “I really enjoyed talking to you. I know that you aren’t online all the time- can I plan to talk to you again on Tuesday?”
Consider talking with the person more online before you make the leap to meeting in person. If you are using an online dating site like OKCupid or Tinder, then you may very well decide to meet up with the person soon–or immediately. Again, exercise your best judgment. If you meet up with a stranger, tell a friend where you are going, and with whom. Bring your phone with you and, if possible, meet in a public place (such as a coffee shop) during the daytime.
