My mom gave me a hard time a couple of months ago because I asked to borrow her car for a date (I was later bailed on and the date never happened, it was all for the best and that point is moot). Anyway, my mom couldn't believe that I asked. She thought that I was putting her in the position where she had to turn me down and then felt like I had guilted her into feeling bad. I kinda saw her point and felt bad that she felt bad (oh no, are we entering a guilt spiral!), but only because she felt bad.
I explained to my mom that rather than wishing I could borrow her car, I decided to ask. No one ever gets what they want by wishing. You get things by asking for them. I was fully prepared that she was going to say no, but the risk was worth it on the outside chance that she might say yet. Now, this only works if you are prepared to hear the word 'NO'. And if you really want something, you have to be clear about your wants and expectations, and be willing to compromise.
It's worth taking the risk of asking for what you want sometimes. Because, sure, my mom said no when I wanted to borrow her convertible for a date, but she said yes when I asked to drive it over Memorial Day weekend! Though, she wanted to borrow my car then... ;)