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Then, insert in a nice and suave manner your point of view and advice. You can tell him something like:
"Your shirt seems to be very comfortable to wear, Paul. Since this is your very first date, I think Sandra (his date) will be much more impressed if you would wear something like outfit that you wore on my birthday. You look smashing when you put on clothes like that."
Afterwards, make another positive statement. You could say something like:
"You would definitely make a big impact on Sandra. She would fall heads over heels over your gorgeous appearance and cheerful personality. Have a great time on your date, Paul."
Do you think Paul would be offended by such pleasant comments? Not a chance. You have wittingly inserted a slightly negative feedback into a plethora of acceptable and ego-boosting remarks.
People love compliments. They believe they got qualities. They want other people to intensify great abilities that they believe to possess. People wanted to hear their greatness purported from someone else's mouth, and they would be very glad if other individuals would know about it.
So if you want to criticize anybody, remember to praise him first. It will leave a positive impression that you're a nice guy. Then say what you have to say, but in a smooth and non-offensive manner. Finalize with another positive reinforcement to establish a foundation of goodwill.
Michael Lee is the author of "How To Be A Red Hot Persuasion Wizard," an ebook that reveals powerful secrets on how to get anything you want, including how to fully improve your relationships, explode your profits, win arguments, and magically influence others. Grab a sample chapter at http://www.20daypersuasion.com