Should I play his game or be mature?

My crush loves to play games with me. I don't like it but I umed it is part of his insecurity. I am going out tonight to meet up with another guy in his fraternity at my crush's favorite bar. His fraternity brother and I are friends but we flirt every now and then. Last week, my crush told me how he made out with another girl and I was hurt. Should I call/text him tonight to tell him that I'm going out with his frat brother and to his favorite bar?