There is definitely an “art” to conversation. The problem is that most of us are clueless as to what that might be. I mean, how do you start a conversation with a someone you have never met before? I’m sure you know that, as much fun as they are, pick-up lines are the quickest way to have yourself labeled as a loser or psycho. You want to be fun and engaging. Take something simple like “hello” and go a step further. “I thought I would come over and say (use of air-quotes optional) Hello!” And then pause and actually say, “Hello!”. or swap it up after the pause with, “but then I decided against it. You know where I could get some Cheese Doodles?”. And wait for him or her to respond. Congratulations, you have officially “broken the ice”.
Another fun thing I like to do is approach a girl from the side, stand next to her, see what she’s looking at and say, in a low voice, “So, are you planning to steal that?” Just be sure you have a comeback for whatever she says, like, “That’s good, I was going to grab it myself and you had me worried I might have to wrestle you for it”. And remember to keep a straight face.
Your goal should be to stand out, by being original – not so much in what you are saying, but how you are saying it. A key to achieving this goal is to be sincerely interested in what the other person is talking about. Be in the moment. Use humour and tease them a little about what they are saying. You want to create an atmosphere of “play”. Ask unusual questions and tell truthful and off-the-wall stories about yourself and people you know. Purposely misinterpret something they say and put a funny spin on it.

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