Source: Timeline:Post-Island - Lostpedia

2007
Prior to April 5th, 2007
At least Jack and Kate escape the Island under unknown circumstances.
Thursday, April 5th, 2007
"Through the Looking Glass"
April 5th, 2007 is 2 years, and 108 days after contacting Naomi's Ship.
The man in the newspaper clipping dies at 4:00 AM.
Jack has left the island and since become deeply depressed, addicted to prescription painkillers, and alcoholic. He tears the newspaper clipping (which establishes the timeframe) from a newspaper and carries it with him.
Jack contemplates suicide on a bridge, causing a bystander to crash.
April 6th-On
"Through the Looking Glass"
Jack attends the viewing for this person at the Hoffs-Drawlar Funeral Home, and is the only attendee. He tells the funeral director that he is neither friend nor family to the deceased.
Jack calls Kate and requests a meet. They eventually meet up and Jack insists that they have to return to the island and that they should have never left. However, Kate disagrees.

__________________
Please don't give up, Des. Because all we really need to survive is one person who truly loves us. And you have her. I will wait for
you. Always. I love you, Pen

DESMOND: I love you, Penny. I've always loved you. I'm so sorry. I love you!
PENNY: I love you too.
DESMOND: I don't know where I am, but--
PENNY: I'll find you, Des--
DESMOND: --I promise--
PENNY: --no matter what--
DESMOND: --I'll come back to you--
PENNY: --I won't give up--
BOTH: I promise. I love you.

I thought I heard Jack ask for Kennie on one of his phone calls???

Yes I understand he called Kate also

My ears or he slurrin speech

Don't believe so. He was calling Kate each time.