Dowling was born in the townland of Knockballyvishteal, Milltown, County Galway, Ireland in January 1837, the second of eight children, born to tenant farmer Patrick and Bridget Dowling (née Qualter). Following eviction of his family from their home in 1845, the first year of the Great Famine, nine-year-old Dowling left Ireland with his older sister Honora, bound for New Orleans in the United States in 1846. As a teenager, young Dick Dowling displayed his entrepreneurial skills by successfully running the Continental Coffeehouse, a saloon in the fashionable French Quarter. His parents and siblings followed from Ireland in 1851, but the joy of reunion was short-lived. In 1853, a yellow fever outbreak in New Orleans took the lives of his parents and one of his younger brothers. With rising anti-Irish feeling growing in New Orleans, following local elections which saw a landslide victory for the 'Know Nothing' party, Dowling moved to Houston in 1857, where he leased the first of a number of saloons, a two-story building centrally located on the corner of Main and Prairie Streets. He named it the Shades, from the sycamore and cottonwood trees which lined the two streets and shaded the building. Advertised as 'inferior to none in the state' he opened a billiards saloon on the first floor. Dowling was described as a likable red-headed Irishman and wore a large moustache, possibly to make him appear older than he looked, as he was called 'The Kid' by family and friends alike at this time. In 1857 he married Elizabeth Ann Odlum, daughter of Benjamin Digby Odlum, a Kildare-born Irishman, who had fought in the Texas War of Independence, being captured at the Battle of Refugio in 1836. Following Texas Independence, he was elected subsequently to the fledgling Third Congress of the Republic of Texas.