From paulstips.com: "One of the big differences that I've noticed between those who get what they want and those who don't comes down to one simple behavior - whether they're willing to ask for it. Why are some people so afraid of making simple requests? Almost inevitably it's because of the fear of rejection. Certainly if you make a habit of asking for things, you're going to get rejected more often than if you don't. But you're also going to have your wishes granted more often. It's a trade-off - more rejection for more success. And believe me, it's a trade-off that's well worth it. The thing to understand about rejection is that it hurts less as we experience it more. With time, it starts to feel like water running off a duck's back - you hardly even notice it's there. You will become almost immune to feeling let down. Simply look upon rejection as part of the process of moving towards success. If you need to be told no ten times before you receive a yes, then you'd better start working through those no's."
I agree entirely with this sentiment, and would add one explanatory comment. Much of our fear of rejection is an evolutionary relic. Such fear was appropriate in a small hunter-gatherer community in which a single rejection could result in permanent social ostracism, and our genes were shaped by such an environment. But in modern society, communities are fragmented and often non-overlapping, and many of the people you meet today you'll never see again. Retaining this evolutionarily induced caution when interacting with strangers and casual acquaintances is maladaptive and unnecessarily restrictive. When your instincts tell you one thing and your reason tells you another, it's often better go with your reason. Get out there, make a few mistakes, make some slightly outrageous requests, and don't worry about what people think. As long as you don't break the law, it probably won't go on your permanent record.