Sissy/ˈsɪsi/ Definition 1 of 3Pro Tip 1/3Negative Connotation The word 'sissy' can offend someone by implying they’re not brave or strong. Don't call him a sissy; it's hurtful and rude. Pro Tip 2/3Informal Use ‘Sissy’ is not suitable for formal conversations or writing. He jokingly called his friend a sissy for not trying the spicy food. Pro Tip 3/3Stereotypical Gender Roles ‘Sissy’ is often based on stereotypes, expecting boys to be tough. At the playground, the older kids taunted the gentle boy, calling him a sissy.