On the sly Definition 1 of 1Pro Tip 1/3Cultural Context The phrase often implies disapproval or something not socially accepted. He was dating her on the sly because his parents didn't approve. Pro Tip 2/3Slight Disapproval 'On the sly' might suggest that the action is slightly wrong or naughty. She'd been eating sweets on the sly, despite her diet. Pro Tip 3/3Sneakiness Implies cleverness or sneakiness in avoiding detection. Tom completed his project on the sly to surprise his teammates.