Young Diana enjoyed living in the stucco double as she could walk to Howe High School, a place she loved. Each morning she dressed up in her cashmere sweater, long dress, hose, and flat shoes and entered Miss Motley's homeroom class. She loved to draw so Mr. Howard, an art instructor, was one of her favorite teachers. She joined a social club called "Smiles" and hung out with friends after school. After graduating from Howe in 1952, Diana matriculated to Butler University. She continued to dwell with her parents
Then Diana decided to do something crazy. In 1956, she bid her bid parents "farewell" and headed off to New York City with a few other friends. She landed a job with the Benton and Bowls Ad Agency as an art secretary. While she mainly kept the files organized for the executives and ad men, she occasionally helped out the creative directors by posing for test shots before the models would be brought in for the actual photo shoot. Diana had to pinch herself as she met famous people like Norman Rockwell, Grandma Moses, and fashion designer John Weitz. She also fell in love, but in 1964 she learned that her mother was ill so she packed up her bags and made the long ride home to Irvington, where a new life awaited her.
|Diana Wilkens posed for this shot with her date, Paul Ross, in her home at 5120 East Washington Street in 1954|
|All Dressed Up: Diana Wilkens on the front steps of 5120 East Washington Street in 1954|
|Diana Wilkens playfully held up "Ming" to the Christmas wreath hanging on the door at 5120 East Washington Street in 1955.|
|Mr. Wilkens fed a tame squirrel on the rear stoop of 5120 East Washington Street in 1954|
|Exciting Times: Diana Wilkens and Alan Pentaleri posed for a test shoot for an ad while working at the Benton and Bowls Ad Agency in New York City in 1958.|
|The Wilkens family moved into the double at 5118-20 East Washington Street in 1950 would remain there throughout the decade.|