Striking up a conversation online is a lot like talking in person, only easier. You’re in the comfort of your own home or in some other familiar surroundings, so it’s easy to relax and just be yourself.
One key is to put a little twist on the normal questions. Instead of “Hi, how are you?” try, “Hey! How has your day been so far? Did you do anything exciting?” Try not to let her get away with one or two word answers, and make sure you don’t give short answers either.
You’re a man of the world, so portray your life as full and fun. “Fine,” “nothing,” and “not much,” will not win you the girl of your dreams. Tell her about the truck that almost ran over you when you were getting into your car after work, or the movie you just picked up from the Red Box machine. Any little thing could lead into a conversation, if she picks up on it.
You can also “branch out” from things she mentions. She drove to the grocery store. So ask her what kind of car she drives. You just paid $60 to fill up your tank? Ask her how much does it costs her? What supermarket has the best prices or freshest meats? Just keep connecting the dots and the conversation will keep going.
It’s best to avoid obvious come-ons like “Hello, beautiful.” Instead, tell her she reminds you of your favorite teacher in grade school or has a smile like a certain actress (who just happens to be beautiful). Ask her how she likes the dating website or instant messenger she’s using right now. Is she online often? Tell her you never know what to say to a girl online. Just put some words together and build a conversation on the responses.