Well, I think it's just like you said. If you let someone know what you need you are taking a risk, they may or may not give it to you. But I think you need to take that risk. For one, people want to feel needed, they need to even

. Really needing something and being evasive about trying to get it is much worse than being direct and giving the other person a chance to give you what you need and feel good about themselves. Plus if you don't ask you often won't receive, people in general are all very self-focused so keep in mind that almost no one is going around guessing at what you need from them... but that doesn't mean that people don't want to help!
In therapy it has been very embarrassing for me to admit how much I need my therapist and how much he means to me. I don't know why it is... because I'm sure from his point of view it's good if anything to hear someone cares so much. It would be worse if I needed him but kept it hidden and went about trying to get what I want in evasive ways, and then was angry or passive aggressive when I didn't get it. Maybe you can start small by asking for something and see what happens. I'm not saying you'll always get it, but you might be surprised how much people do follow through for you. I think most people are generally good natured and want to help out when they know how to, so long as whatever you need isn't too crazy an ask. Good luck!