I really enjoy this show! And Issa is quite a beauty!

This show is certainly conveying a message about her life as an independent, beautiful, strong, awkward, silly, fun, black woman - just making her way through this thing we call life. But it's also showing how she's going through the same things that women, IN GENERAL go through. We have ALL found ourselves singing, rapping, give ourselves pep talks, acting goofy, etc. while getting ready and looking in the mirror. And it's FUNNY! We ALL have made ourselves beautiful for some things that have let us down. We all have dreams and have been afraid to do something about them. We all have checked out what's going on with our exes one time or another. We all question our relationships, jobs, coworkers, friends, etc. She is like a black Hannah Horvath in how she is blatantly narcissistic, the difference being that she is somewhat apologetic about it. The two are alike as well, by way of their strength but also how they question themselves. While the show is called "Insecure," Hannah seemed a lot more insecure than Issa. But it's only the third episode, we still have a lot more to learn about Issa. What I have noticed is that she doesn't let on that someone or something is causing her insecurities. And if she does, she only makes it clear to her best friend Molly, after a little coercing from Molly. (And in the pilot's voice-over when she she states some of those insecurities, of course.)
I have to admit, I look up to Issa! She's gorgeous and funny! I love her beautiful smile! And the woman keeps it real!

Seriously though, I would NEVER ask a person a question like, "What's on fleek?" Nor would I ask them what it means, just because he or she is black. But other people might and it shows the struggles some black people have to put up with because of stereotypes. We all have had to, or may still have to, deal with the daily struggles of stereotypes.
Issa is just making light of her own, and it's pretty damn funny!