Lyric discussion by raviolicadillac 

Cover art for Sideways lyrics by Let's Go Sailing

I think this is about a someone who starts to find out that they have deeper feelings for one of their friends than they had thought.

"I have no problems Dipping in my feet But the trouble comes when I have to jump."

I think this refers to the fact that the person has no trouble flirting and playing around with their friend, but to "jump" all the way in, or to tell them how they really feel (I love you more than that), is too much. this is a beautiful song.