Confused

A guy I who has been trying to talk to me has mentioned several times that he wanted to take me out for dinner. He also has talked to me about his family, shown me pics of his mom, called me cute, would ask how my day was going, said he wanted to keep getting to know me, see me for lunch every week, etc. but today, after seeing a picture of a friend of mine, said she was pretty. I jokingly said, “what? Am I your wingman now?” And he said “I wouldn’t mind”. But then later he said he was kidding. After I said “are you??” He said “I don’t know what to say”. So I don’t think he was kidding. Now I feel like a fool for opening myself up to this guy, even though he sent me so many strong signals. Am I stupid? Is he just messing with me? Or is he stupid and not being serious about all of the flirting? I need help