Those pics are from 2017
https://www.tmz.com/photos/image_jpg_20170601_6a034cbb32c0526797199bac7bcbed71/
https://www.usmagazine.com/celebrity-news/pictures/kylie-jenner-and-travis-scott-relationship-timeline-w505074/coachella-love-w505086/
Not for sure but a search of April to June shows this…
He was talking about Trump and Twitter
https://www.wired.com/2017/04/jack-dorsey-on-donald-trump/
Here is the link to the search, hope it works
https://www.google.com/search?q=jack+dorsey+2017&client=firefox-b-1-d&tbs=cdr:1,cd_min:4/1/2017,cd_max:6/1/2017&ei=CL7WX5yTHYrWtAag5bHgCA&start=10&sa=N&ved=2ahUKEwict7Opp8ztAhUKK80KHaByDIwQ8tMDegQIDxA1&biw=1920&bih=966