Be more informal and casual in your conversation. Choose "hey" rather than "hi". Ask him, "how's it going?", or "what's up?". If he asks you the same thing, don't say "same" because that will give him an impression that you are dull. Tell him anything about your day, even if it was stupid. (Saying 'nothing' could make it a dead-end conversation.) That would make him laugh and think that you have a good sense of humor!
Never gloom. Don't tell him what a bad day you've had - at least at the first chat, save that until you know him better. Otherwise, you may come off as gloomy or boring.
Show him who you really are. Get yourself a webcam, and get on to him. That not only gives him something to talk to, it gives him things to talk about. You can now show him things in the room or on yourself. If he has one too, ask if you can watch, if he doesn't offer. Be careful not to expose too much!
Avoid asking him short-answer questions. Questions like "Did you see that movie?" is one of them. The answer would be either Yes or No. That's too short. Elaborate and say "That movie looks pretty good. I wanna go see it sometime." It can give both of you a new topic. Do not forget to reply to everything he said.
Talk about anything; his favorite band, color. Don't talk about yourself all the time, considering you may come off as self-centered and self-obsessed. If he has mentioned an interest that you both have in common, talk about that! Reader Poll: We asked 178 wikiHow readers, and 59% agreed that bonding over a common interest is a great way to start a conversation with someone online. [Take Poll]
Know how to end the conversation. When he says he has to go or if you have to go, say something like "I'll see you tomorrow" or "talk to you later". Something that will imply future plans or chats with him.
Be careful about talking to him too often. Chat with him often enough to keep in touch, but not every single day. There is a chance it will become less and less special if it becomes too frequent.
Only ask a guy out online as a last resort only. It's much better to ask him out in person. When it comes to more serious times in a relationship, never ask anybody out online. This also works with break-ups.
Finished.
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