Issa New Bae? Insecure’s Season 3 First Trailer is Here June 5, 2018Blackaphillyated By Dymond Alexis Twitter: @dymondalexis Instagram: @dymondalexis Issa Reunion! Insecure is coming back August 12th and guess who her boo is? Daniel! Remember at the end of season two Issa returned to her ex’s house and it looked like things weren’t too promising. Check out the teaser above!