Lyric discussion by punkwillsaveus 

Cover art for Windows In Heaven lyrics by We Are The In Crowd

I would think that Tay (lead singer) has lost someone close to her and they are now in heaven. She wants them to see how she ended up and wants to see if they're proud of her for accomplishing her dream. (If you could see me now Would you be pleased and proud)

Its just showing how far she has gotten, even if she did struggle sometimes and basically she is asking if they, whom is in heaven, see that.

Love the song

Song Meaning