After the release of "Dear Winter", AJR put out a statement that "the song was a letter to [Ryan's] future child about the awkwardness of dating".

[3] Ryan Met explains in an interview with iHeartRadio he wrote "Dear Winter" "after I asked a girl to hang out and she said no.

[5] "Dear Winter" is composed in 44 common time and in the key of F major, with a tempo of 94 beats per minute (bpm).

[10] The version received additional production from Michael Mangini with vocal effects and added instruments such as drums, strings, and synths.

[14] "Dear Winter 2.0" is composed in 44 common time and in the key of F major, with a tempo of 94 beats per minute (bpm).