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I give money all the time.
One time I was in Mcdonalds and they were tossing this old homeless guy out for asking for fries so I bought him a meal.
I think its more a matter of your natural generosity than experience. Some people just give, others really aren't comfortable with it.
PS. I have also bought penniless inebriated sorority girls food in the wee hours of the morning.
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