Sean Penn Ready to Propose?

Sean Penn is reportedly planning to propose to Charlize Theron.

Friends close to the couple, who began dating at the end of last year and flew to Hawaii to celebrate New Year's Eve together in December, predict the Milk actor and the South African actress will get engaged in the very near future, but insist they haven't started making wedding plans just yet.

An insider told PEOPLE.com that they "wouldn't be surprised" by a proposal, adding, "But she's not engaged - yet."

The duo, who went public with their relationship at Sean's third annual Help Haiti Home gala in January, were "inseparable" when they flew to Cabo San Lucas in Mexico for Valentine's Day weekend in February. "They held hands everywhere they went," an eyewitness said at the time.

The 53-year-old actor is set to direct his Oscar-winning girlfriend and Javier Bardem in The Last Face, which is expected to begin filming in Africa later this year.

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Simon Cowell Plans Proposal

Simon Cowell is planning a "special holiday proposal."

The music mogul will reportedly ask pregnant girlfriend Lauren Silverman to be his wife during his annual festive break and has even splashed out on a ring. "Simon has an engagement ring, but is being secretive about the proposal. 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," a source said.

Simon is said to be excited about becoming a father for the first time next year, and is looking forward to Lauren's baby shower. "He is beyond excited about his son He loves feeling the baby kicking and acts very proud that he will be a father. Lauren's friends are planning a New York city baby shower that Simon will attend," the source added.

A spokesperson for the X Factor boss refused to confirm his engagement plans. "The matters are private and there will be no comment on it," they said only.