Clearly about a guy that has a girl that strung him along and he has/is convincing himself of the futility of the situation. The first verse means he would fall for her bad but there was something she was witholding, commitment or ahem. The last 2 lines of the chorus clarify this, he keeps up with her over and over and then its clear it won't work out, the whole thing about filling his cup has a second meaning besides a booze refrence. The second verse refers to a time or the times when he sees her at a place (probably a bar, club or coffee shop) and just seeing her, wants her, and thinks to himself that if she thinks it didn't turn out it was because of something she withheld.
Clearly about a guy that has a girl that strung him along and he has/is convincing himself of the futility of the situation. The first verse means he would fall for her bad but there was something she was witholding, commitment or ahem. The last 2 lines of the chorus clarify this, he keeps up with her over and over and then its clear it won't work out, the whole thing about filling his cup has a second meaning besides a booze refrence. The second verse refers to a time or the times when he sees her at a place (probably a bar, club or coffee shop) and just seeing her, wants her, and thinks to himself that if she thinks it didn't turn out it was because of something she withheld.