POINTPEOPLE

In my opinion, pointpeople are the easiest and most effortless way to start a conversation with a stranger you are interested in.  Going straight up to the person you are interested in poses many problems, mainly awkwardness.  So, let's set the scenario...

You are in a public gathering and you see the person you are interested in.  A few feet away is a person who you can easily start up a casual conversation with.  This person is your pointperson.  So you walk up and start up a casual convo with the pointperson and ya'll start talking about iPods, for example. 

YOU: "Hey I noticed you had an iPOD.  How do you like it?
POINTPERSON: "I like it a lot.  It's neat"
YOU: "I hear that.  (Getting excited-->) Oh man, have you heard about the new iPod coming out soon?"
POINTPERSON: "No."
YOU: "Oh wow.  You've got to check it out!  It's got digital audio recording, live television, and a video camera all in one!  Oh man."

Now, this is the important point in the conversation where you bring the person you are interested in into the conversation.  If the person or group of interest was close enough in proximity to you and your pointperson, then they should have heard or seen your enthusiasm for what you were talking about to your pointperson.  So, quickly turn around to the person or group you are interested in and quickly ask them...

"Oh man. Have you guys heard about the new iPod?  It's amazing.  It has digital audio recording, live television, and a video camera all in one!  It's amazing."  Depending on their response, you can either stay turned towards them and keep talking or just turn back around to your pointperson.  Either way, chances of rejection are greatly reduced.

You turning around and asking the person you are interested in must appear spontaneous and like they are the first people you saw to ask and that's why you asked them.  Nine times out of ten, if your delivery is calibrated correctly, you will hit a hook point where they become somewhat interested and invested in what you have to say.  Boom.  You can take the convo anywhere after this.  The good thing about spontanaeity in this situation is that it shows that you don't have an agenda by talking to them.  Therefore, they won't have their guard up or be wondering what your intentions are.  You are just spontaneously talking to them as one social being to another because that is what social beings do.  They mingle with each other.

I've found that pointpeople are the easiest and least awkward way to open a set you are interested in.  If you don't hit the hook point then don't worry about it.  Just turn back around to your pointperson.  Your pointperson is your friend.  Respect.  Signing off.  Cheers.