I'm having trouble with prayer and my faith

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I have never doubted the existence of God and I have always prayed and trusted him.

Lately, I think I am going through what the saints call, a "dark night of the soul."

Lately, I have found myself praying for myself, that I will have an increase in holiness, thanking God for all that I have been given and asking him for guidance and virtues.

I have also been praying for my former best friend and an ex girlfriend. She has left the church, and is battling anti social tendencies, emotional and anger issues, and what may be depression. It also troubles me that we did not leave on good terms.

I have been praying for another former friend. He was never religious, but he has become quite obnoxious, rude, selfish and has embraced new age, neopaganism while continuing to slam Christianity.

He knows of my beliefs and I have told him that I find it uncomfortable when he does this, but he continues to jump at the chance to mock Christianity or discuss various conspiracy theories about the government and the church (Hitler was a practicing Catholic, the Pope is a dictator, etc.).

He has been my friend since Kindergarten, but hanging out with him is an exercise in patience and a source of constant headaches. All I can do is pray for him.

I have also been praying for two uncles and an aunt that have left the Church.

Lately, I have been fighting feelings of despair when I begin to pray. Whenever I begin to pray, I sometimes feel like my prayers aren't going to matter or be answered, that God has something else in mind and I'm wasting my time.

Whenever I begin praying for them, I begin to feel stressed and hopeless, impatient. At times, I feel like giving up, that it would be easy to say one prayer and move on with my life.

I know this isn't true. I know God hears all our prayers and answers them in some way. I know I must always pray for sinners and that with faith and virtue, God will act.

These feelings, though, are constantly appearing during prayer. It feels like prayer itself is becoming my cross to bear. It is becoming increasingly stressful just to pray, especially for these two people, but I am .

I'm not giving up, but I need your prayers, for myself and these two people, for God's mercy, for virtues, for conversion, and for unwavering faith in the Lord. I have been praying to the Blessed Virgin, the Saints (particularly St. Jude, St. Jerome, St. Faustina, and St. Anthony) as well

I've been reading the Diary of Sister Faustina and it has been helping. Also, does anyone else have anything to say? Advice, thoughts?

God bless you all.