Diana Trask was born in Melbourne, Australia on the 23rd of June 1940. Diana’s parents, Lew and Thelma Trask, were married in 1926 and had three children Peter, Patsy Anna and Diana. Patsy Anna sadly died at the age of two. They had a country house at Warburton and Lew ran a furniture business in Melbourne. Diana was educated at the Lilydale Convent and Presentation Convent in Windsor. At the age of 17 Diana won the Swallow’s Parade television talent quest on Channel Seven. This led to a job miming the popular songs of the day on Channel Nine in a show titled The Astor Show. By 1958 Diana Trask was singing her own ballads on the local television variety show In Melbourne Tonight hosted by Graham Kennedy.
Diana made her first recording on the W&G label - Comes Love with Tommy Davidson and his Orchestra. In 1959 American promoter Lee Gordon signed her as the support singer for the Stan Freberg tour of New Zealand which also featured the Australian Jazz Quartet and Frank Ifield. Lee was impressed and immediately signed Diana to tour Australia with the Frank Sinatra show. Diana was rehearsing My Funny Valentine when Frank Sinatra and his manager came into the room. The manager exclaimed, "This kid can’t sing that song! That’s Frank’s song!” Frank quietly said, "If the kid wants to sing the song let her sing it. She sings it better than I do.” So, Diana’s version of My Funny Valentine was in the concert. Diana opened the show and there were calls from the audience to "get on with it” but they soon were won over by the beautiful young singer. Diana’s memories of that concert were that she was very conscious of the starched petticoats she was wearing and trying to hold her dress down. Stan Freberg, a very good friend of Frank’s, was also a support act. Sinatra was very impressed with the young Melbourne singer and suggested that she should try her luck in the US. He very kindly spoke to people on his return and Diana decided to go. In 1960 Diana Trask opened at the Blue Angel Nightclub in New York and Sinatra sent a good luck telegram. Frank Sinatra was there later in the season with a group of about 20 people. Many months of hard work followed with tours and singing engagements. After an appearance on Don McNeil’s Breakfast Club, Diana was noticed by Mitch Miller and this led to a recording contract with CBS. Diana released several albums and singles on the CBS label.
In 1961 Diana landed a regular singing spot on the national television series Sing Along with Mitch and was signed to a three year contract by NBC television. It was a "Sing Along Show” hosted by Mitch Miller with a strong male chorus and Diana Trask was one of the featured singers. Sing Along with Mitch was produced and directed by Bill Hobbin and choreographed by James Starbuck (who became a great friend of Diana). The show was screened nationally on the Nine Network in Australia. Diana became a household name in the US and was a big attraction when she performed in Las Vegas. Diana worked with the big names in show business and formed friendships with performers such as, George Burns, Danny Thomas and Jack Benny. She tested for a role in the 20th Century Fox film State Fair opposite Pat Boone as part of her 20th Century Fox starlet contract. There were constant trips backwards and forwards between Australia and the US for concerts with Pat Boone and Sammy Davis Jnr.
Around this time, the young singer was on a plane when Johnny Mathis introduced her to Thom Ewen. Johnny invited Diana and Thom to make up a foursome in a card game to while away the time. Little did anyone know that the chance meeting would lead to many happy years of marriage.
Thom and Diana were married in Australia in 1962. In the same year, their first son Shawn was born and Patrick was born in 1964. Thom was now Diana’s manager. In 1964 the family returned to Australia for The Diana Trask Show on the Nine Network. This was a national half hour variety show which was produced by Thom.