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2.
1. A person who can ease their way through things, typically using words. Also may be a player. It seems this person may have a way with words and always knows what to say.

2. They may also be cunning, wily, and might be willing to lie, cheat, or steal to get what they want.
You can refer to the song "Smooth Operator" by Sade, read the lyrics, and it may help you.

It has good and bad connotation, it all depends on how it's used.
1. Dang, that girl don't look it, but she is one smooth operator. She just got a date after a five minute conversation with him.

2. That man is a smooth operator, he just dumped a girl and has a date with two new ones.
by Kosha February 25, 2008
 
1.
Someone who can handle multiple situations in a fashion that can only be described as "Awesome, spectucular, and, above all else, awesometacular".

Usually a smooth operator is someone who tends to be "on top of things", and in is usually in control of any given situation.
If he/she isn't in control of a situation, they usually find a way to gain control of it to make it more awesome for everyone involved.

Smooth Operators are rarely in trouble, and, when they are, they can usually get out of these situations quickly, elegantly and with a zero percent chance of casualties.
Kevin is a smooth operator.

Julie thinks "That Kevin is one smooth operator."

Everyone agrees, and life is awesome.
by Kevin Coffey April 01, 2005
 
3.
When a man tucks his penis between his legs so that it looks like he has a vagina then displays the final product to others.
Rather than mooning the crowd, I gave them the Smooth Operator.
by Markrushon September 06, 2006