In the early 1980s, Shawkat met Bushra al-Assad, who was at that time studying pharmacy at Damascus University. Bushra was the first child and only daughter of Hafez al-Assad, and she had a close relationship with her father. Bushra's father and her younger brother Bassel al-Assad were strongly opposed to Bushra's relationship with Shawkat, who was ten years her senior and a divorced father of five from a modest background. Bassel briefly had Shawkat jailed in 1993 to block their relationship. However, there is another report stating that the reason for his imprisonment was related to his wrongdoing.