I think there is hope. The last time he might have been too inexperienced or too shy,.... you know, just not ready to date (I'm just guessing, I don't know his background). Going from 16/17 to the age of 18 is a big jump in maturity, changes in who you are, etc. It's possible he's feeling he's ready, and those comments is him putting out feelers to see if you would be on board with it. He's just being shy about it, or nervous because of what happened the last time..remember you were the one that dumped him. It may have broken his heart, so he's worried about being rejected. I would give it a little more time, but respond more positively to his slight flirtations. It may encourage him to be more forthcoming with his intentions. Not many 18 year old guys have the nut sack to ask a girl out no matter how well they know you. For example at my school reunion (20 year I think, ya ya I'm old), all these guys I knew in school came forward and admitted they liked me but were too afraid to ask me out. I thought that was just silly.