Jolly along Definition 1 of 1Pro Tip 1/3Casual Encouragement Used when motivating someone in a friendly, non-pressuring way. When she hesitated to join the game, I jollied her along with a warm smile. Pro Tip 2/3Positive Vibe Implies a cheerful or upbeat approach to persuasion. He needed a mood boost, so we jollied him along by recounting fun memories. Pro Tip 3/3Subtle Persuasion It's about influence without direct pressure or obvious argument. I'll need to jolly her along with gentle hints if we want her at the surprise party.