Winifred Cooper’s birth as a middle-class expatriate followed parental decisions to embark on challenging mobile employment and adventure. However, the chapter shows how expatriate opportunities worked for young girls in unique, gendered ways. The expatriate social mobility argument here takes a more complex turn, charting a growing girl’s ability to exploit frequent travel and greater freedoms of privileged life abroad. Her education and social life shifted frequently between sites in Georgia, London and Tehran, and later Ahwaz, fostering a degree of maturity and linguistic ability. Her engagement with local politics and multicultural friends in Georgia, her work as a telegraphist, her popularity as a multilingual and fashionable ‘young lady’ at the Persian court and among Tehran expatriates, and management of successive hopeful suitors, underline the potential of expatriation to enable women’s independence and cosmopolitanism. Told mostly through a diary and letters, it ends with a compelling account of Winifred and Edgar’s early love story and a fashionable expatriate wedding in Tehran. It moves from two unknown English men, prospering in overseas service, to a complex dynamic of how expatriate identity could be exploited by the next generation and contribute to an unconventional, cosmopolitan marriage.