The son of Eleanor (born c.1827) and Charles Wooldridge (born c.1824), Wooldridge was born in East Garston and joined the Royal Horse Guards in 1886. He married Laura Ellen "Nell" Glendell (1873–1896) in 1894 when his regiment was posted to Windsor. However, as his commanding officer had not given permission for the wedding to take place she was "off the strength"' and so was unable to join her husband when his regiment moved from Windsor to Regent's Park barracks in London, forcing the couple to live apart and putting a strain on the marriage.