He's nuts, plain and simple. He's confused and is still looking for that brass ring. Of course, he's not where he wants to be, i.e., 18, single, having the time of his life. He honestly doesn't have a clue as to where he wants to be right now.
You've got to let comments such as this roll off your back. There's absolutely no way we can analyze his every sentence because he's bouncing all around and hasn't landed yet.
BTW, I'm glad you did something special for your special day.
Sit quietly, the answers will reveal themselves when you least expect them to. The past is gone, the present is a gift and you need to focus on today, allow the future to reveal itself when it is ready.