Good approach buddy. I felt you were asking for some validation when you kept asking "you enjoyed the conversation" and that wasn't necessary because she looked like she did enjoy the conversation.
Keep them coming
Hey man! Thanks for the comment, that’s just one of the things I say and I react according to her answer basically. It’s something that I do quite often, I don’t do it to get validation from her more to know how she feels. It’s a great way to build up the conversation.
If she says “ This is weird” I go with my “ What can be more normal than 2 human beings talking?” I will upload a video soon where I pretty much say that and she had no come back for that… At the end it’s just a man and a woman talking.