MAKE YOURSELF WEEP
Ibn al Qayyim rahmatullah alayh says in Zaad al-Ma’ad “It [weeping] is sought after to soften the heart and to increase one’s deep fear of Allah (swt), and it is not for the sake of being heard or seen by the people.”
Making yourself weep earns less of a reward than actually weeping. However it is the way towards weeping, that is because the one who makes himself weep, is among those who strive heard and fight their souls, and take account of themselves, and endeavor to attain the pleasure of Allah azza wa jal. Allah (saw) says “And those who strive hard in Us [Allah’s cause] We will surely guide them to our paths.” [29:69]
So whoever strives to make his soul weep, then Allah (swt) will guide this person to sincere weeping and give him success in achieving it.
On the authority of Anas (raa) who related that he heard rasulullah (saws) say “O people weep, for if you cannot weep then make yourself weep. Indeed the inhabitants of the hellfire will weep until their tears pour down their cheeks, as if they were streams until the tears are used up and then blood will pour down, and the eyes will be covered with ulcers.” [hasan in sahih at targheeb wat tarheeb]
Reflect over the way rasulullah (saws) ordered us to weep or to make ourselves weep.
On the authority of Ibn Abi Mulaykah who said “We were sitting with Abdallah ibn Amr (raa) on a rock. He said, `Cry and if you cannot cry, then make yourself cry. If only you knew, you would pray until your back broke and cry until you lost your voice.'” [alhakim reported in marfu’ form and it is sahih, adhdhahabi states its authenticity, ibn al mubarak reported it in mawquf form]