Is it small talk or is he into me?

So, I have a friend that I'm into, yet I'm not sure if he's into me. One thing that he does whenever the two of us get lunch together is that he asks about my love life in some form. Once he just casually asked how my love life was. When I said complicated, he's like, "but nothing serious, right?" I laughed and said no. Just the other day, he took me out to lunch and asked about a hookup he heard that I had earlier in the year. I avoided talking to him about it because I didn't want to give him the impression that I'm just a hookup. He clearly set up the conversation to be able to ask me about that. Did he have any intentions by doing so? Also, when I told him I don't hookup with people anymore, he said not to worry as he doesn't judge. What should I make of that?