Should I continue talking to him?

[Light of Grace]

Ok I have been talking to one of my guyfriends a lot lately we'll call him Aaron. I met Aaron last year through a friend of mine named Jessica around this time last year. So me and him have known each other for a year but didn't really start talking a lot until 2 months ago. Lately we've been hanging out together just us with the one exception where he went to a play with me and my family (that being my mother, sister, and brother. Note: They all liked him. First time meeting him) Well I knew that him and my friend Jessica had dated for a few months and he ended up hurting her, but not saying that she didn't have a part in the problem. I told her I liked him and she said that she didn't know if she wanted to (note2 they slept with each other) but she told me to be careful if I do. Now onto him. Aaron brought up a girl that he had liked while we were in the play, in a sorta sharing what happened the last time he went to a play but stopped bringing it up. Now lately he'll send me random messages or leave comments on my FB and we do talk a lot more since we started hanging out alone. The two big things that are a cause for questioning is he's getting ready to go to texas for air force training and my friend still has yet to give me an ok. I really like him but don't know if I should keep talking to him in a flirting way or should I just not wait for my friend's ok and go for the long distance relationship?

I apologize if this is a little confusing.
ok these answers so far have not made since. I'm asking if I should pursue a relationship with him even though he's leaving and that my friend hasn't given me an ok to date her ex