Would you lend money to family and friends?

The last few months have been really frustrating. Many people have been coming to me to borrow money. Mainly my brother and a friend. To be fair, when I lent them money in the past they paid it back. But it was small sums of money, I'm currently owed $985 and $700, it's been a couple of months now. They keep saying next week or this day, that day. But when the time comes.. nothing.
More people (3 people) have asked me to borrow money, sums between $100 - $400. I declined because I'm still waiting on those two payments. People know I have a good heart and often try and take advantage. After I get paid back, I'm going to be more careful about lending out money. After all I am also trying to get my fiancees together.