Haunted, I'm sorry your time at the fair wasn't the best. I'm going to suggest that when he begins talking about his life, the possible ow, etc., that you either change the subject or walk away. You and your daughter do not need to be subjected to this utter gibberish.
He wants you to be okay and find someone because then it alleviates the guilt he has for doing what he's doing, as well as then it would be okay for him to bring this so called fantasy relationship out in the open.
Walk away, do not sit there and listen to that stuff because all it does is upset and frustrates you and your daughter. There's a time to be a friend and listen and then there are those times when you need to say I've got something else to do or be somewhere else.
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.