<p>You have to judge these things on the fly a lot of the time. If you are meeting in person or even talking on the phone, you can use your instincts (if your social instincts are good) to determine when you are close to crossing a boundary. To add to the confusion, some professors accept things and will do things that others won’t. But if you ask a blunt question and don’t get a straight response, you should never push it. The last thing you want to do is annoy an LOR writer – or purse an LOR writer who obviously doesn’t want to do it. You have to judge when you should back off.</p>