longb

I think this summarises. Move on.

He may be flirting, how do you feel about that?

It might not be too late but you need to align your expectations with your abilities to achieve your goals. Usually prioritising and dealing with one issue at the time taking into account how each goal depends on the others helps.

Difficult to say how long it will take or whether the third round could work but I'd definitely leave it with him - the ball's in his court.

Although your extensive description may lead to think these circumstances are very specific, this situation is typical of relationships at work. I'd just keep work and private life separated. Over the years I observed that this is the best way to keep things good at work and have a happy relationship outside.