and it starts with middle school...ya know, where most of us start to become self aware and get very insecure behind the comments of others on our appearance, social status, etc.

Her being an adult, you'd think, would be immune to it but the kids actually went in on a few of her adult issues (career choice, relationship status, social status) and even drove it home with clowning her appearance.

It immediately set the tone for the episode:

-Career choice: you can see her wondering 'why the hell am I here' everytime they show her at her job
-relationship status: both Issa and Molly go thru it, from different angles
-social status: envy of Molly's career/status
-appearance: though she made it something fun, the whole lipstick thing and her trying out personalities based on the lipstick color was a direct b-line to insecurity...until she decided to just be herself

...and it was funny.