One of the most awkward things I have ever had to do was to ask a relative for money. I was about to graduate college, broke but debt free, and I desperately needed a car. So I asked a relative to give me a loan.
Yes, it was awkward, and to my surprise, she refused. While I know it was awkward for her too, she refused the loan in a way that made me feel like it was nothing personal. She knew why you should never lend money to friends or family. Instead of simply rejecting my request and leaving me to find an alternative solution on my own, she helped me find a way to afford a car.