In the 2012 episode "Gone Abie Gone," Grampa disappears. Homer and Marge follow a clue to a once-fancy nightclub called Spiros, where 35-year-old Abe worked as a busboy following the departure of his wife Mona. He also played piano and wrote songs, and he teamed up with Spiros' singer, Rita, to became a successful musical act. They fell in love, got married, and were about to tour Europe, only for Abe's duties as a father to keep him in Springfield. Abe and Rita split up.
That's not Abe's only misbegotten romance. Just before he fought on D-Day in World War II, he met an English woman named Edwina, with whom he had a one night stand. When the Simpson family visited England, Abe reconnected with her... and her daughter, a Homer lookalike, meaning Abe is her father.
Abe Simpson is a romantic, but also a philanderer. While courting Mona, the woman he'd marry and Homer's mother, he had a fling with Gaby, a prostitute and worker in a traveling carnival. After one night together, she left town, but when the carnival came back a year later, she had a baby son. They surrendered him at the Shelbyville Orphanage, and he grew up to be auto magnate Herb Powell.
