How and how not to start a conversation: a comparison analysis

Here is how to start a conversation:

Stranger Man waves to me

SM1: Hello!

Mush: Hello.

SM1: Do you remember me? I'm the guy who tipped you five thousand dollars the other night.

Mush: I don't work nights and I don't have five thousand dollars!

SM1: oh maybe it was some other girl.. haha I'm just kidding. I just wanted to have a conversation with you and get this type of effect.

Mush: and what effect is that?

SM1: To have you stand here and talk to me. Otherwise I don't think you would. You're very beautiful.

And so the conversation continued..

Let's clarify for a bit- firstly SM1 was not a good looking guy but wow. his confidence was beyond phenomenal, geez, look what you can do with a little self esteem. And secondly, I knew I was being conned- come on guys I've read that book too-however, however am I still being conned if I know and I enjoy it?

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Here is how not to start a conversation [four hours later]

Mush gets into a lift with three other men, SM2, a janitor and a dealer. [Haha, that sounds like the beginning of a bad joke.] No-one is talking.

Stranger Man 2 [smiles at me]: Hey Elizabeth, hows it going?

Mush: Sorry?

SM2: [mimics my intonation] sorry? [rolls his eyes to the janitor] God, why are people so boring today?

The janitor is looking at him quizzically. I'm trying not to punch him in the head. The entire lift is .. angry silence...

I get out of the lift and mumble.. "Douchebag" which is not really the most eloquent thing I can say-but is probably the most appropriate.