We’ve Got The Official Trailer For HBO’s Insecure Season 2 Mastermind June 29, 2017 04:09 pm It’s. Going. Down. Introducing the official trailer for #InsecureHBO S2, July 23 on @HBO. pic.twitter.com/KJ5CQm1LyV— INSECUREHBO (@insecurehbo) June 29, 2017 If you didn’t watch season one of Insecure yet, do yourself a favor and catch up so you can be up-to-date for the second season when it starts July 23.