In this episode, Professor Frink uses science to attract women while Grampa uses a drug to relive his happiest memories.
Mr. Smithers reminds Mr. Burns about Valentine's Day and tries to convince him to let the employees leave early to stay with their loved ones.
While enjoying the party with Marge, Homer gets a phone call from Grampa saying that he is alone and scared that a cat who can smell death is staring at him.
Frink replaces his glasses with invisible blue contact lenses and uses shoe lifts for him to look taller, but even a droid that he programmed to say "yes" still thinks he is not attractive.
At the Simpsons' house, Marge discovers that Bart is taking advantage of the old people's hallucinations to win money on gambling.
Though the nurse hides the drugs in the library, Grampa finds the pills and takes them, so he can start hallucinating and win Mona back, running out of the Retirement Castle and into a 1940s-esque world.
During his hallucination, Marge, Bart and Lisa convince Grampa to leave the past behind and live in the present, where there are people that still love him.
Marge thinks they should wake up, but is distracted by Homer calling attention to Dean Martin's presence.