“If you can’t cry about yourself you need to learn a lot more to see and then feel the great gap of what we can be and what we are. We need to put ourselves in a private place with no phone and no distractions and learn the Hakdamah and first perek of Mesilas Yeshorim and see how we measure up.”
“Crying” can be symbolic and metaphorical. It is unfair and unreasonable to say that if you can’t physically cry, you’re doing something wrong. It is possible to feel a world of emotion without shedding a single tear.