Starting in 1928 and lasting until the mid 1930s, Ryan would enter into a romantic relationship with Rosamond "Róisín" Jacob, a fellow Republican and Socialist. The pair met through Ryan's Irish language classes. Because of a number of factors, such as the age difference between the two (she was 40 and he was 26 when they met, at a time when the norm in Ireland was that women should be younger than their partners), their different religious backgrounds (Ryan was nominally a Catholic, Jacob nominally a Quaker) and the fact that they were unwed, the relationship was considered "an affair" and they believed that it had to be kept a secret.