I think this song is a reflection written to a former love that possibly was ended by him to pursue his music career. "If I never lived without you" I would have died in obscurity never pursuing his dream. After "years spent with feeling" it was painful having to choose but "by the end of summer" he felt he was healing. Maybe as times got hard he was having second thoughts wanting reasurrance of "the love he found knowing it was gone" and trying to laugh it off. He is reaffirming the love he had. He never really committed to the love but "now you know I'd try.
I think this song is a reflection written to a former love that possibly was ended by him to pursue his music career. "If I never lived without you" I would have died in obscurity never pursuing his dream. After "years spent with feeling" it was painful having to choose but "by the end of summer" he felt he was healing. Maybe as times got hard he was having second thoughts wanting reasurrance of "the love he found knowing it was gone" and trying to laugh it off. He is reaffirming the love he had. He never really committed to the love but "now you know I'd try.