He probably DID get some women that way. So he thought he could buy you, too.
Similar story here: A friend and I were sitting at a food counter at the mall. We were 16 years old. Middle-aged man sat next to us. He smiled at us and started talking about his family. He seemed like a good family man - a nice, jolly kinda fellow with a pot belly. He showed us photos of his wife and kids. The kids were in their teens too. We both smiled and said something like, "Nice family."
Then he put his wallet away, motioned to both of us, and said, "So how much?"
I kid you not.
At first we were confused. But he just laughed as if we were playing with him, and he said: "Oh, come on. How much?" Once we understood, we said, "We were just being nice to you because you were talking to us about your family." He laughed and walked off. I'm sure we weren't dressed like nuns, but we weren't dressed like prostitutes either. He must've pulled that stunt in the past and it worked.
Honestly, I don’t know what gets into some men.