Frank Sinatra was nearly 50 years old when he met actress Mia Farrow, who was only 19. Yet Frank Sinatra decided to win her affections by taking her on a private plane ride to Palm Springs. To further show his affection, Frank Sinatra took Mia Farrow’s deaf cat, Malcolm, along for the ride.

When a man not only cares for a woman but her cat at the same time, you can see how that would win over any woman’s heart. Eventually Frank Sinatra and Mia Farrow broke up, partly because of their age differences. Mia Farrow said, “Poor Frank, saddled with such a child. I would be falling asleep at the table at Las Vegas, trying to talk to people about their cats. He was very patient with me.”

To learn more about Frank Sinatra and Mia Farrow (and her cat), click here.