Many thanks to ixio5 for sharing his selfie with Keanu on instagram. While the tags say Rome 2017, Keanu’s hair says otherwise. The photo was most likely taken on December 9, 2014 when he filmed the episode of the Italian show, You’ve Got Mail (C’e Posta per Te), that aired on March 7, 2014. It was covered here.
Many thanks to teamheadkick for sharing his selfie with Keanu on instagram and to @rebeccaedwardsc for tracking down that the photo was taken in April 2015 at The Replacements concert.
Many thanks to eugeneashin for sharing his photo with Keanu on instagram. Photo is a throwback and the comment indicates it is from after the release of John Wick. Based on his hair, I’d say the photo was taken some time in Spring 2015.