Thinking on this, I feel like it is my close family that asks how much I have lost. My sister has been my number one supporter and checks in with me every Sunday morning after my weigh in. But it is also because I then use her as a sounding board for what I did through the last week food and exercise wise. My coworkers and other friends never really ask. They ask how I am feeling and I get compliments on how far I have come, but that's it.
If someone does ask, don't be afraid to tell them that is too personal. Only share what you are comfortable with. In the beginning, I didn't really share how much I lost with anyone. I didn't want to admit to my highest weight or where I was at in the process. I was completely ashamed of myself and didn't feel like that was something to celebrate. I feel like I didn't get comfortable sharing it with my family until I was about 50 lbs down. Do what feels right for you.