[1] The track marked Ross's first new release after signing a major label deal with Universal Music Canada and The Core Entertainment.

[2] Ross and co-writer Mason Thornley were at a Virgin Hotel rooftop bar in Nashville, Tennessee going through ideas when they first began to write "On a Different Night".

[3] Ross referred to it as a "personal track," noting that he "wrote the song about going out places with an ex-girlfriend and how difficult it was to revisit them without her and to have fun knowing that we used to share those moments."

He added that he "wanted listeners that may have gone through a similar situation to relate and connect with the lyrics while giving the energy and momentum to uplift the song.

[6] Erica Zisman of Country Swag referred to "On a Different Night" as "nostalgic, heartbreaking, and relatable," stating that it "paints the picture of what it’s like being out, but not really being in the mood to drink and have fun."