De Cruz met Coral Phipps, a girl from Penang, at her cousin's house in Kuala Lumpur, fell in love with her, and asked her to marry him. She pointed out all the impossible-to-scale barriers. He did not have a job, any money in the bank, and could be picked up by the police at any time. Then, Coral had promised herself that if she survived the Japanese Occupation, she would travel around the world a bit. From Penang she had moved to Kuala Lumpur and then Singapore, where de Cruz had found her a job in the Social Welfare Department. A three-year courtship followed. He asked her to marry him and they would see the world together by working their way around. He told her also that he wanted to visit the Soviet Union to find out from the horse's mouth why the MCP had taken to the jungles. She made a bargain with him. This was August 1948. By the end of that year, one or both of them should have gone abroad. If he left first, she would join him. They would get married and make their way to the Soviet Union.

De Cruz began to look for a job to finance the trip. Doors in Singapore were closed to him because of his reputation as the leader of the Eurasian Progressive Movement, the MDU and the PMCJA. But, one day, he ran into Jacob Ballas, an old friend who was now working for the Sun Life Assurance Company of Canada, which had a large branch office in Singapore. Ballas gave him a job — selling life insurance to the Malacca millionaires whom de Cruz had got to know. He took up the offer and, in Malacca, again met Tan Cheng Lock, whose friends bought two or three large policies from him. Ballas was disappointed when de Cruz told him that he was leaving Singapore, but accepted his decision. It was towards the end of 1948. He decided to go to Karachi and visit his INA friend, Inayat Hassan, who had saved him from the pursuing Japanese soldiers at Saigon. Meanwhile, Coral continued working as confidential secretary to Sir Percy McNiece, the last Governor of Singapore. She planned to save enough in six months to join de Cruz.