This is a song about uncertainty and doubts.

In the the first verse, he speaks about the doubts he had(or still has) of the person he is with. "time that called for space, unclear where you drew the line." He is not sure about her because she probably hesitated to go into the relationship and wonders why but can't fully answer this. So he wants to just stop thinking about it and hope for the best in future.

The second verse is speaking about the doubts he has in himself. He has a history; probably failed relationships and for reasons most likely of his fault. so he wonders if he really has it in him to change. In the end, there is no way to answer that unless you take the chance and see for yourself so he "...closes his eyes..." and jumps in

All in all, the song is saying take a risk and don't keep asking questions you cannot fully answer that will hold you back.