Don't start off naked or with parts of your body exposed. Girls go to Chatroulette or Omegle for "different reasons" than guys do: girls think that it is fun and exciting, and they want to feel attractive and wanted. If your webcam presents naked or exposed people, a girl is going to think that you think of her as an object instead of a person, and she'll click away. Look your best, their first impression will be looks, so try hard to be dressed well and looking dapper. Don't look like you just stepped out of bed with your pajamas still on. That will scream laziness. Start off with a prop, like a guitar or a flag, and hold it there or do something interesting with it. All you need is for a girl to be intrigued, and she may start to talk to you. Don't directly face the camera. Move your webcam so that you aren't directly facing the camera at first. You can come off as a little too intense, even if that's not your intent.
Talk for a little bit first. Get a good conversation going. Be your most interesting self. Any girl on chatroulette could go to her local bus stop and talk with a boring dude if she wanted to. But that is not what she wants. She wants you to be the most interesting man alive, like the guy from the Dos Equis commercials. Familiarize yourself with a little bit of French, Spanish, German, Chinese, and Japanese. Be able to say "hello" and "how are you?" in each language. That way, when you start chatting with someone from a different country, you can whip out your amazing language ability and surprise her in a good way. When in doubt, ask questions. If you run out of things to talk about, be sure to ask lots of questions. Questions are generally easier to come up with than interesting observations, and they make great conversation starters. Ask her personal questions, but not anything too personal. What was her childhood like? What does she like reading to listening to? What is her favorite food? Where is her dream vacation?
Flirt. After chit-chatting for awhile, start to get flirty. She will feel more comfortable around you, so they will most likely respond positively. Be playful. Girls love guys who have a great sense of humor and are playful. A great sense of humor is hard to come by, but everyone can be playful. Mess around with your props in a non-threatening way. Make visual illusions using your webcam. Experiment with your lighting. The world is pretty much your oyster; you just have to learn how it play with it. Do impersonations of famous people if you can. Ask her if she knows _______, and then knock an impersonation out of the park. The more you get her laughing, the better off you will be.
Smile, girls absolutely love it when guys smile. That is because people want to be around other people who are happy; not only is attractive, it's infectious. Laugh at her jokes. Girls are often told to laugh at guys' jokes, but guys can always do the same. It feels good for her to have someone she can laugh with. It will make her feel comfortable. The more comfortable she is, the higher your chances of success are.
Don't be pushy. If she's not ready, don't bug her. You'll get more flies with honey than with vinegar. Don't force things, let things develop organically, and project your confidence whatever happens. Confidence is a huge turn on for girls.
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