Hakeemul Ummah Hazrat Moulana Ashraf Ali Thaanwi Sahib رحمه الله has said that a friend wrote to him expressing his grief because of his inability to cry. Hazrat Thaanwi رحمه الله explained to him that this grief is the actual objective since it is the grief of the heart. Shedding tears is not the objective. Hazrat Thaanwi رحمه الله further advised that he should express shukr (gratitude) unto Allah Ta’ala جل جلاله for having bestowed to him the true objective; i.e. the crying of the heart. There are numerous pitfalls in this path of Tasawwuf. Many have slipped and fallen.
(SOURCE: MALFOOZAAT OF HAZRAT MOULANA ASHRAF ALI THAANWI SAHIB رحمه الله, PART 6)