Penelope Penny Widmore is the love of Desmond's life, but he deems himself unworthy of marrying her after her father tells him so. Penny is the heir to a great fortune and Desmond was a lowly theater worker. Desmond gives up on Penny and then enters the Royal Scots Regiment for a time before being dishonorably discharged and put in prison. Desmond enters a sailing race around the world -- which Charles is hosting -- in an effort to prove himself to Penny. She never fully gave up on finding Desmond and has people all over the world looking for him.