Do people ask you for money extremely often?

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No because my cloths & grooming resembles a beggar more than they resemble someone with money. People have occasionally asked me for drugs or if I wanted to buy drugs thou

People who know me know that I always have a little pocket money, and sometimes ask for a dollar or two. I refuse them, which is how I manage to buy small items(invariably cheap sodas) when I want them.

Once, a guy asked me for a nickel in an Ohio turnpike plaza, saying that was how much he was going to be short that much on his toll. I am not certain that he really needed it, or if he wanted me to take out my wallet so he could grab it and run, but I was counting out change for a vending machine at the time, so I handed him a nickel, and he left me alone.

I need to be better on saying no to money requests. I feel gullible after finding out I'd not get paid back a supposed loan or that they were a crappy person.

Yes. It's because asking for stuff is more or less of a joke from where I live.

On a serious side, I don't give in. I almost never give in.
I don't borrow or have others lend my money unless either I or the other have the means to pay back less than few hours or change.
I'd likely give things than let someone borrow. I don't like it if I have to hold my breath on it.

Bums or people acting like bums occasionally ask me for money but I always say No. My girlfriend's sister ask to borrow money every month. I loan to her but she eventually pays me back only to borrow again a couple weeks latter. She's terrible at managing her money.

Sometimes they ask for $$

Several times a day, usually they ask for cigarettes and drugs and a light

If I can help, I help. My ability to help financially is limited as Social Security is my only income, but I help whenever I can.
It makes me happy.

"If beings knew, as I know, the results of giving & sharing, they would not eat without having given, nor would the stain of selfishness overcome their minds. Even if it were their last bite, their last mouthful, they would not eat without having shared, if there were someone to receive their gift. But because beings do not know, as I know, the results of giving & sharing, they eat without having given. The stain of selfishness overcomes their minds."
Siddhartha Gautama; the Buddha

"Just practice good, do good for others, without thinking of making yourself known so that you may gain reward. Really bring benefit to others, gaining nothing for yourself. This is the primary requisite for breaking free of attachments to the Self."
Eihei Dogen zengi

"If you see that other people are suffering, and you're in a position to help, you focus not on their karmic past but your karmic opportunity in the present."
Thanissaro Bhikkhu

“Our job is to love others without stopping to inquire whether or not they are worthy. That is not our business and, in fact, it is nobody's business. What we are asked to do is to love, and this love itself will render both ourselves and our neighbors worthy.”
Thomas Merton

"What actions are most excellent?
To gladden the heart of a human being, To feed the hungry, to help the afflicted, To lighten the sorrow of the sorrowful, and to remove the wrongs of the injured."
the prophet Muhammad

"Let the man who has two coats give one to the man who has none; and let the man who has food share it with others."
Jesus of Nazareth

Exactly.