He lived in Lula, Georgia with his parents, Clyde and Gertrude, and sister, Blanche, until his enlistment in the U.S. Army in May 1940.

The raid was meant to bomb the Japanese in response to the December 1941 attack on Pearl Harbor.

In a well-known account of the raid, Thirty Seconds Over Tokyo, author and raider Ted Lawson mentions eating blueberry pie with Lt. Truelove, ignoring the battle-stations drill.

On April 5, 1943, his unit was attacking an Axis shipping convoy in the Mediterranean Sea.

Of the crew of six on board, Truelove, Captain Richard T. Norvell, and Technical Sergeant Warren V. Richardson were not recovered and were declared Missing in Action (MIA).

He was also awarded a Chinese air force medal by Madame Chiang Kai-Shek.