Dear Winter is a song about a future son Ryan, one of the AJR band members wishes to have. Although the song is sung by Jack, Ryan’s brother and band mate, Ryan confirmed in an interview that he wrote the song, and that it is, indeed about a boy. He pictures Winter growing up, from birth to taking his first shot on his 21st birthday. Repeatedly though, it seems he is snapped back to reality, with lines like “But sh*t, I gotta meet your mom first.” The whole song is so honest and it just gives it a cute, heartwarming feel.