This is one prayer for the gift of tears but not the one I was thinking of which is in my old Latin missal that I do not have with me - it's ok to pray for such a gift and I have found when answered it makes my prayers more real. I love the Seven Sorrows Mysteries and one of Mary's promises attached to this is a deeper understanding of the mysteries. In this deeper understanding we cannot help but get to know Jesus and Mary better. Your experience sounds much like mine. Prayer for the Gift of Tears St. Augustine, Bishop and Doctor Translated by M.F. Toale, D.D. (PL 40, Book of Meditations I, Ch. 36, col. 930..) 1. O Lord Christ, Word of the Father, Who came into this world to save sinners, I beseech Thee, by the innermost depths of Thy mercy, cleanse my soul, perfect my actions, put in order my manner of life, take from me what is harmful to me, and what displeases Thee. Grant me what Thou knowest is pleasing to Thee, and profitable to me. Who but Thou alone canst make clean what was conceived of unclean seed? Thou art the Omnipotent God, Infinite in mercy, Who makest sinners just, and givest life to the dead; Who changest sinners, and they are sinners no more? Take from me therefore whatever is displeasing to Thee; for Thy eyes can see my manifold imperfections. Stretch forth, I beseech Thee, the hand of Thy mercy, and take from me whatever in me offends the eyes of Thy goodness. In Thy hands, O Lord, are my health and my infirmity. Preserve me in the one; heal me in the other. Heal me, O Lord, and I shall be healed, save me, and I shall be saved: Thou Who dost heal the sick, and preserve those who are healed, Thou Who by Thy nod alone dost renew what is ruined and fallen. For if Thou wilt sow good seed in Thy field, there is need also to pluck from it the thorns of my sins by the hands of Thy mercy. 2. Most sweet, most kind, most loving, most dear, most precious, most desired, most lovable, most beautiful, pour out into my breast, I beg of Thee, the fulness of Thy sweetness and charity, so that I shall not think of or desire what is carnal or earthly, but rather love Thee alone, keep Thee alone within my heart, and upon my lips. Write with Thy finger upon my heart the precious remembrance of Thy sweet name, that no forgetfulness may ever from there erase it. Write Thy will and Thy law upon the tables of my heart, that always and everywhere I may have Thee and Thy holy precepts before my eyes, O Lord of unending sweetness. Inflame my soul with the fire thou didst cast upon the earth, and willed it be enkindled (Lk. xii. 49), so that with welling tears I may offer Thee daily the sacrifice of an afflicted spirit, and of a contrite heart (Ps. 51). Sweet Jesus, O good Jesus, since I long for it, and implore it of Thee with my whole soul, grant me Thy chaste and holy love, that it may fill me, hold me, possess me, completely. And grant me that visible sign of Thy love, a cleansing ever flowing fountain of tears, that these tears may also bear witness to Thy love in me, that they may show, that they may tell, how much my soul doth love Thee: that in the too great sweetness of Thy love it cannot withhold its tears. 3. I remember, O Lord, that good woman of whom Scripture speaks, who came to Thy House to implore of Thee a son, that after her prayers and tears her face was no longer changed (I Kgs. i. 18). But remembering her great virtue, her great constancy, I am afflicted with grief, overcome with shame: for I behold my miserable self lying prone upon the ground. For if she so wept, and persevered in weeping, this woman who sought a son, how should not that soul lament, and cease not lamenting, which loves and desires God, and desires to come to Him; how it should not weep and mourn, day and night, loving only Christ? (Ps. xli. 4.) Look upon me, and have pity upon me, for the griefs of my heart are multiplied. Grant me Thy heavenly consolation, and despise not this sinful soul for which also Thou didst die? Grant me, I beseech Thee, in Thy love, the inward tears that can dissolve the chains of my sins, and fill my soul for ever with Thy heavenly delight: so that I may merit to obtain, if not together with Thy true and perfect monks, whose steps I am unable to imitate, then at least with Thy devoted women, some little place within Thy kingdom? 4. There comes also to my mind the wondrous devotion of another woman, who with pious love sought Thee, lying in Thy tomb; who when Thy disciples departed from the tomb did not depart from it, but sad and grieving sat there, and long and sorely wept, and getting up again, in tears, searched with anxious eyes in every corner of the tomb, that somewhere she might see Him Whom she looked for with such fervent longing. Once and again had she entered and seen the tomb, but there is never enough to the soul that loves: for the crown of a good work is perseverance. And because she loved more than the others, and loving wept, and weeping sought, and seeking persevered, so did she merit to be the first of them all to find Thee, to see Thee, to speak with Thee (Jn. xx. 11-17). And not this only, but the first to tell the Disciples themselves of Thy glorious Resurrection; Thou commanding her, and gently instructing her: Go, tell my brethren that they go into Galilee, where they shall see me (Mt. xxviii. 10). If she then so wept, and continued weeping, the woman who looked for the Living with the dead, who with the hand of faith touched Thee not, how should not that soul mourn, and cease not from mourning, which believes in her heart, and confesses with her lips, that Thou art her Redeemer, ruling from heaven, and reigning everywhere? How ought not such a soul both weep and mourn, which loves Thee with all its heart, and longs with all its being to see Thee! 5. O Sole Refuge and Sole Hope of the unhappy, to Whom we can never pray without hope of mercy, for Thy sake, and for Thy Holy Name’s sake, grant me this grace, that as often as I think of Thee, speak of Thee, write of Thee, read of Thee, preach of Thee, that as often as I remember Thee, stand before Thee, offer Thee sacrifice, prayers and praise, so often may I weep, the tears welling sweetly and abundantly in Thy sight, so that tears may be my bread by day and night. For Thou, King of Glory, and Teacher of all virtue, by word and by example, has taught us to weep and to mourn, saying: Blessed are they that mourn: for they shall be comforted. Thou didst weep for Thy dead friend, and Thou didst weep over the city that was to perish (Jn. xi. 35). I beseech Thee, O Good Jesus, through these most blessed tears, and through all Thy tenderness, by which Thou didst wondrously come to our aid who were lost, grant me this grace of tears my soul so longs for, and now begs of Thee. For without Thy gift of it I cannot possess it. By Thy Holy Spirit Who softens the hard hearts of sinners, and moves them to tears, grant me the grace of tears, as Thou didst grant it to my fathers, in whose steps I should follow: that I may bewail my whole life, as they bewailed themselves by day and night. By their prayers and merits who have pleased Thee, and most faithfully served Thee, have mercy on me Thy most pitiful and unworthy servant, and grant me the gift of tears. Water me from above, and water me from below, that day and night tears may be my bread. May I become in Thy sight, O my God, a sacrifice, rich and full of marrow, through the fires of Thy compunction. May I be wholly consumed on the altar of my own heart, and may I as a most acceptable holocaust, be received by Thee as an odour of sweetness. Grant me a strengthening fountain, a clear fountain, in which this defiled holocaust may be continuously washed. For though by the help of lily grace I have offered myself wholly to Thee, yet in many things I daily offend Thee, because of my great weakness. Grant to me, therefore, this gift of tears, O blessed and Lovable God, especially because of the great sweetness of Thy love, and also for a remembrance of Thy mercies. Prepare this table before the face of Thy servant, and grant me this power with regard to it, that as often as I will I may be filled from it. Grant me, in Thy kindness and Thy goodness, that this Thy chalice (Ps. xxii), so good and so inebriating, may quench my thirst. Let my spirit long for Thee; let my soul burn with Thy love, forgetful of all vanity and of all misery. Hear me, O My God; hear me, O light of my eyes, hear what I ask of Thee; and grant that I may ask of Thee what Thou wilt hear. Kind and gentle Lord, be not hard to me, because of my sins, but because of Thine own goodness receive the prayers of Thy servant, and grant me the answer to my prayer, the answer to my desire, through the prayers and merits of my Lady, Mary Virgin, and of all the Saints. Amen.