Ileana's engagement to Archduke Anton of Austria, Prince of Tuscany, was announced at Freiberg on May 4, 1931.
King Carol II, eager to remove his sister from Roumanian affairs as she had taken Helen's side in the divorce, arranged for his cousin, the Prince of Hohenzollern, to invite Ileana and Anton to the family's castle at Umkirch. This was done, and Ileana became engaged to the archduke. Other guests at the castle included Queen Marie, her brother-in-law, Grand Duke Kyril of Russia and his daughter, Grand Duchess Kira Kirillovna and the Prince and Princess of Hohenzollern.
Ileana is said to have met Anton in 1929 when she accompanied her mother on a visit to Spain.