Dolly met 18 year old Antonio Sinatra in 1912, and crept into boxing fights dressed as a boy to watch him. She had a foul mouth, and often didn't stop talking. Dolly spoke both fluent English and several Italian dialects, and had the ability to write, unlike her husband. Dolly was known to never forget or forgive offensive comments thrown at her. She was also known for her organisational skills, and had singing skills inherited from her father. Frank Sinatra's singing skills came from both her and his father, who were both talented singers. Her parents, who were of a higher class than Marty, detested the marriage. 
Dolly volunteered to become a military nurse during the First World War, but was turned down. When Frank was three she worked as a chocolate dipper, covering the candy with chocolate and identifying them with letters.
Dolly chained herself to Hoboken town hall in 1919, as part of the campaign for women's votes. Soon she was the head of the local Democratic ward. The Irish, who ran Hoboken, used her to buy the Italian votes. She provided people with jobs, welfare checks, bags of coal and health information. She was close to both mayors throughout the period, which was known for its corruption. 
Dolly also became a midwife, and performed abortions, which were illegal at the time. She did this free of charge, and saved many reputations, as unplanned pregnancy was considered a disgrace.
Dolly had blue eyes and light skin and, during her youth, strawberry blond hair. She was very small. Her parents did not like their relationship, so Dolly and Marty ran away together to Jersey City, getting married at the city hall on Valentine's Day just a year after they met. They returned home and later got remarried in a church with their families.
It took Dolly two years to get pregnant, and she was hoping for a girl. She went into labor in December. She was less than five feet tall and weighed ninety pounds, and the size of the baby caused her a lot of agony. She was accompanied by midwives, a doctor, her mother, sister Josie and a neighbor. Fearing for Dolly's life, the doctor used forceps to pull the baby out. The baby appeared to be dead, but one of the women in the room managed to revive him with water. The experience left Dolly unable to have more children, leaving Francis Albert Sinatra her only child.