Saint Catherine is not promoting the morbid idea that we should love just any kind of suffering for its own sake.  There is lots of unhealthy suffering in the world – all kinds of misery where love is absent.  The suffering of the Cross in which those who love God delight is really an “anguished love”, and not the suffering brought on by self-indulgence, self-pity or self-loathing.  

These forms of ignoble sufferings always debase one’s dignity.  They always involve subordinating the truth about who we are to pleasure, possessions, or power or some combination of these.   These kinds of self-hatred are really a hatred of God.  St. Catherine clumps such unhealthy suffering together under what she calls “selfish self-centeredness” and she believes that the Father vehemently detests these kinds of destructive self-preoccupations.  She hears God say about those who wantonly choose this kind of misery, “Their filth harms only themselves, not Me.”  (See The Dialogue, 121)

How does she look at this self-centeredness?   It is a tragedy over which we should weep for one another.   This is because she sees selfishness over and against the great purpose for which we were made.   We are meant to minister the bright warmth of the sun, but selfish love makes us dark instead.  This description almost anticipates what astronomers today call “black holes.”  Saint Catherine describes this lack of self-knowledge as a matter of eternal peril.

Without the liberating self-knowledge that comes from God, self-love is such a trap of rash judgment that it renders us incapable of loving those entrusted to us.  We are callous to the poor and to all those God loves unless we humble ourselves and turn to the Son of the Father.  In response to our selfishness to God and the those He loves, the Father gives us His Son on the Cross.  The Father yearns for us to reach out to the Cross of Christ where alone we find the freedom of the His love for us and freedom from ourselves.

For her, the Holy Cross is always the bridge from the
alienated misery of sin to the merciful love of the Father.   It is on this bridge that we become familiar
with Christ, that we confess our sins and come to feast on His Eucharistic banquet.   In the Eucharist, this bridge becomes a table.   It is a feast of faith which establishes
real communion with the Lord in our lives.  
The more we partake of Him by faith, the more we are taken by Him in
love.  A desire to share completely in
Christ is born in the soul.   Nourished
by the mystery of the Cross, she puts into the mouths of such souls the words
of St. Paul, “I glory in the hardships
and shame of Christ crucified” (see 2 Cor. 12:9-10).

The beauty and force of Saint Catherine’s thought, however,
is that she does not attribute her teaching to herself, but rather to God the
Father.  She is Christ-like: her teaching
is not her own (see John 7:16).   For her, the Father is the one who delights in the beauty and splendor of His Son.  If the Father is disappointed by sin, it is secondary to the Father’s vision of what is good and holy in the world.  He sees through the disguise of suffering into the beauty of His Son’s love at work.   He sees souls so motivated by love for
Christ that they dare to traverse the Mystery of the Cross.  The Father is delighted that they are attracted to His Son’s anguished love because He delights in this love too.   He always sees the Son in whom He is well pleased reflected in the suffering of those who share in His Son’s anguish for the salvation of the world.   Reporting
what the Father spoke to her in prayer, she explains:

Such souls glory in the shame of my only-begotten Son….[they]
run to the table of the holy cross, in love with my love and hungry for the
food of souls.   They want to be of
service to their neighbors in pain and suffering, and to learn and persevere in virtue while bearing the marks of Christ in their bodies.  Their anguished love shines forth in their
bodies, evidenced in their contempt for themselves and in their delight in
shame as they endure difficulties… To such very dear children as these,
suffering is a delight and pleasure is wearisome, as is every consolation and
delight the world may offer them. (The
Dialogue, 78)

The references to “children” in this passage are not merely sentimental terms of endearment, but they have theological weight in the broader theological tradition.   The attitude of trust in the face of suffering implied in this passage really is the attitude of a child, the kind of child the Lord declared would inherit the Kingdom (see Luke 18:17).   Saint Catherine’s spirituality is marked not by great achievements of psychological gymnastics.  Rather than elaborate systems of meditation, the prayer she advocates is humble, a simple movement of the heart to the Father.  Such prayer is commensurate with the faithful remnant of God’s people, the persecuted who hope in the Lord.  The Father judges these suffering children, these anawim, these lowly and despised as “very
dear.”   There is something in this that
anticipates the “Little Way” of Saint Therese of Lisieux.    

If the humble suffering of His little ones is exalted above pleasure by the Father, it is
because He judges these things in relation to His crucified Son, the One who
offers fallen humanity the bridge to His mercy.   One notes throughout the Dialogue that the Father’s condemnation of sin contain almost a reluctant note: His desire that sin should be punished is always secondary to His hope that the sinner will come home.  The Father sees the whole drama of sin through the obedience of His Son,
His Word, His Eternal Utterance from which all things come and in which they
find their ultimate end.

Furthermore, the Father’s hope for His children does not stop with their liberation from sin: He also wants them to have the joy of sharing in His Son’s work of redemption.   If the
Father finds His rest in His Son, it is because the Son knows the peace of perfect obedience, the suffering obedience of love.  The Father longs to see the obedient love of His Son at work in his beloved children.  This is how they will participate in His Son’s redemptive work.

Obedience – to welcome another into one’s heart so that they might find their rest there.  This means tenderly accepting the will of another into one’s own heart.  It is treasuring ones neighbor’s desire as one’s own, to allow the pain, the joy and the plans of another to define one’s life out of tender love.  This vulnerability of heart is rarely possible between sinful people and that is why, instead of obedience, we relate to one another in different forms of submission or rebellion.  In contrast, the divine suffering of obedient love in our humanity reveals the very life of God.   Saint
Catherine personalizes this truth: since the Father rests in His Son’s love, the Father also rests in those who are animated by the anguished love of Christ, “I am always at rest in
their souls both by grace and by feeling.” (The Dialogue, 78).

The hope of conversion lives in these lines.  It is a call to come to our senses.   The soul in which the Father rests no longer allows itself to suffer self-indulgence, self-pity or self-loathing.  The Eternal Father is not content with
sin.  That is why He sent His Son, to
free us from these dehumanizing burdens that we might be raised up, that we
might realize the greatness of our humanity.   
For Saint Catherine, Christ frees humanity from sin by setting hearts on
fire with charity, “The fiery chariot of
my only-begotten Son came bringing the fire of my charity to your humanity with
such overflowing mercy that the penalty for sins people commit was taken away…
There is no more need for slavish fear”  
(The Dialogue, 58).

Those who welcome the flaming chariot of God’s Son – humanity on fire with divine love – soon discover that their own humanity is on fire too.   Burning with the suffering love of Christ, pleasure, security and power no longer drive them.  They are content with suffering all kinds of inconveniences and hardships for the sake of Christ (and for those entrusted to them) because they are driven by the fire of the Father’s very charity Christ’s burning humanity has brought into our own humanity.

When there is no fear of death, suffering takes on a different meaning, and men and women find the freedom that sees hardship through the eyes of God.   If the Father contemplates hardship through the lens of the Cross, then, when we cross this threshold with Christ, we gain an invincible perspective.  Bound to Christ, we find ourselves bound to one another in suffering love, a love that suffers anything that the dignity of one’s neighbor might be protected.  United to our Crucified and Risen Master, fear of sacrifice melts away before the burning fire of divine mercy and tender friendship.

This is the perspective Saint Catherine invites us to share when she describes souls that find pleasure wearisome and rest in suffering.   To be nourished with divine love is to find a courage that lifts us above our own nature and the self-centeredness to which it is subject.   In the face of the fear that inhibits our nature, this fear of not being able to save ourselves, this fear of losing ourselves, Saint Catherine shows us, through the eyes of the Father, how communion with Christ crucified infuses our hearts with the audacity of anguished love.    

The passages from The Dialogue come from Catherine of Siena: The Dialogue, translation and introduction by Suzanne Noffke, O.P. with a preface by Giulliana Cavallini, Classics of Western Spirituality, New York: Paulist Press (1980) 112, 144-145.