Lollipop is about Franco (Prithviraj), a young man who runs an automobile workshop near the beach. Franco's friend Eby (Kunchacko Boban), a junior doctor in a nearby hospital, has a huge crush on Franco's sister Jenny (Roma), a college student who faces a lot of problems with her enemy Rose (Bhavana) in college. Rose and Jenny argue with each other every time they meet. Franco tries to solve the problems between Rose and Jenny, but fails. In the meantime, Franco falls in love with Rose.
Paachi (Jayasurya), a pickpocket, enters at this stage. Paachi tries to pickpocket Franco, but is caught red-handed. Later, they become friends and Paachi becomes a worker at Franco's workshop. Paachi coming into Franco's life and how Franco tries to settle the Jenny-Rose fight forms the crux of the story. Actor Rajan P. Dev plays Rose's dad Chandikunju, who runs a finance company. Chandikunju has a bitter relationship with Eby's dad, played by Sreekumar. Comedian Salimkumar portrays Fr. Kuriakose, a priest who is also a lawyer.
Lollipop is scripted by Benny P. Nayarambalam. Music is by Alex Paul. Azhagappan wields the camera; art direction is by Joseph Nellikal and costumes by S.B. Satheesh.