"Shoulda Known Better" is a song co-written and recorded by Canadian country music artist Tyler Joe Miller.

[4] Miller wrote the song with his two close friends, Dan Swinimer and Jeff Johnson, while staying in the mountains of British Columbia on a writing retreat.

[5] After a night of drinking, the trio was "a bit slow" and we’re writing a slower ballad, when Miller felt they had to "switch gears.

[6] In a press release, he added that the "song tells the story from the perspective of the 'sucker' of a guy who fell in love and got burnt again by this girl and goes on to say that this type of person should come with warning signs, but they never do".

[1] Gabby Shukin of CJVR FM described "Shoulda Known Better" as a "fun, high energy song," that is "perfect for summer".