updated 11/19/2013 AT 3:00 PM ET
•originally published 11/20/2013 AT 9:55 AM ET
It sounds like Simon Cowell is undergoing some major changes in his personal life.
“Simon has an engagement ring, but is being secretive about the proposal,” a source tells PEOPLE. “Simon is flying to the Caribbean for the Christmas holiday. Lauren will join him for parts of the holiday trip. Simon could be planning a special holiday proposal. It seems he will definitely propose.”
Cowell, who seems “very happy” with Silverman, is also “beyond excited about his son,” the insider says. “He loves feeling the baby kicking and acts very proud that he will be a father.”
Adds the source: “Simon is being supportive of Lauren’s divorce settlement with Andrew [Silverman]. Simon just wanted Lauren to get a quick divorce so they could start their new life together. Simon has mentioned that Andrew had a couple of divorce conditions that are not ideal, but he has not talked about the details.”
As for reports that the settlement prohibits Cowell from meeting Lauren’s son [with Andrew] until 2015, the source confirms that Cowell “does not have any contact with her son.”