Back in their college years, Grandpa Wolfe would constantly try to persue Winnifred, only to be rejected every time. In Grandpa's mind, Winnifred was into him but was just too shy to act on her feelings. What really happened was that Grandpa was a massive sleaze and Winnifred found his attitude repulsive.Decades later, when the two met on a cruise ship for senior citizens, Grandpa tried to chat her up once again, but Winnifred only expressed disappointment that he still hadn't matured. At that moment, the cruise ship ran into the Bermuda Triangle. While there, all the senior citizens aged backwards, turning into children, teenagers and young adults. Rocko and Heffer, the only young adults on the ship at the time, became geriatrics. Grandpa and Winnifred reverted back to their college selves. When old Rocko was thrown overboard, Grandpa tried to save him, but nearly drowned in the process. Winnifred, seeing this selfless side to Grandpa, developed feelings for him.
The cruise ship eventually found its way out of the Bermuda Triangle and everyone went back to their original ages. Winnifred and Grandpa then became a couple.